Ru(II)-Catalyzed Cross-Coupling of Cyclopropenes with Diazo

Dec 18, 2017 - Herein, we report a Ru(II)-catalyzed carbene dimerization of cyclopropenes ... (5) Among the various transformations, transition-metal-...
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Cite This: J. Org. Chem. 2018, 83, 1026−1032

Ru(II)-Catalyzed Cross-Coupling of Cyclopropenes with Diazo Compounds: Formation of Olefins from Two Different Carbene Precursors Bo Wang,†,§ Heng Yi,†,§ Hang Zhang,† Tong Sun,† Yan Zhang,† and Jianbo Wang*,†,‡ †

Beijing National Laboratory of Molecular Sciences (BNLMS), Key Laboratory of Bioorganic Chemistry and Molecular Engineering of Ministry of Education, College of Chemistry, Peking University, Beijing 100871, China ‡ The State Key Laboratory of Organometallic Chemistry, Chinese Academy of Sciences, Shanghai 200032, China S Supporting Information *

ABSTRACT: Formal carbene dimerization is a convergent method for the synthesis of alkenes. Herein, we report a Ru(II)-catalyzed carbene dimerization of cyclopropenes and diazo compounds. The yields are up to 97% and the stereoselectivity are up to >20:1. Mechanistically, it has been experimentally demonstrated that the catalyst reacts with cyclopropene first to generate a Ru(II)−carbene species, which is attacked by nucleophilic diazo substrate, followed by dinitrogen extrusion to form the double bond.

B

is necessary. In this regard, the groups of Davies2b and Sun2c,d have made significant progress (Scheme 1, b). Recently a new strategy to achieve formal carbene dimerization has emerged.3 In this strategy, a nucleophilic diazo substrate is set to react with a nondiazo carbene precursor (Scheme 1, c). In 2001, Barluenga and co-workers achieved the reaction of Cu(I)-catalyzed diazo compounds with Fischer carbene complex.3b We have subsequently reported a catalystfree reaction of diazo compounds with Fischer carbene complexes.3c Moreover, we have also developed a catalyst-free synthesis of 1,1-difluoroolefins through formal carbene dimerization between difluorocarbene and diazo compounds.3d Other examples along this line include the cross-coupling reactions of diazo compounds with propargylic esters, as developed by the groups of Barluenga,4a Dixneuf,4b and Bruneau and Dérien.4c These reports indicate that control of the chemo- and stereoselectivity is possible following the above strategy, while a major limitation is that the nondiazo substrates are still rather limited. Thus, it is highly desirable to search for other nondiazo substrates for the formal carbene dimerization. Cyclopropene shows diverse reactivity because of the high strain of the small ring, which makes this type of unique compound an excellent three-carbon building block in organic synthesis.5 Among the various transformations, transitionmetal-catalyzed generation of vinyl metal carbene has attracted considerable attention in recent years.5b−e The metal carbene species generated from cyclopropenes undergo typical carbene transformations, such as C−H bond insertions,6 O−H bond insertions,7 and cyclopropanations.8 As a continuation of our interest in the exploration of cyclopropenes as vinyl metal carbene precursors,9 we have determined that it may be

earing a resemblance to the Wittig reaction and olefin metathesis, formal carbene dimerization is an alternative method for the synthesis of alkenes. However, suffering from the competing homocoupling and poor stereoselectivity of the formed double bond, this transformation has not found widespread applications. One way to overcome these problems is to carry out the reaction in an intramolecular manner (Scheme 1, a).1 For example, the groups of Doyle1c and Che1d

Scheme 1. Strategy for Chemoselective Carbene Dimerization

have achieved Rh(II)- and Ru(II)-catalyzed reactions of bis(diazocarbonyl) compounds to construct cycloalkenes. Some other examples of Rh(II)- and Au(I)-catalyzed cyclization of bis-N-tosylhydrazones have been recently reported by the groups of Wang1e and Sun.1g However, in terms of synthetic applications, chemo- and stereoselective intermolecular formal carbene dimerization reactions of two different diazo substrates are obviously desirable but are also more challenging.2 To achieve such a goal, fine-tuning the reactivity of two different diazo substrates © 2017 American Chemical Society

Received: October 17, 2017 Published: December 18, 2017 1026

DOI: 10.1021/acs.joc.7b02634 J. Org. Chem. 2018, 83, 1026−1032

Note

The Journal of Organic Chemistry Scheme 2. Scope of the Cyclopropenesa

possible to use cyclopropene as a source for metal carbene in the formal carbene dimerization. Herein, we report the Ru(II)catalyzed carbene dimerization of cyclopropenes and diazo compounds.10 At the outset of this study, we employed 3,3-dihexylcycloprop-1-ene 1a and methyl 2-diazo-2-phenylacetate 2a as the model substrates to optimize the reaction conditions. First, we tested various transition-metal catalysts, which could react with cyclopropene to generate vinyl metal carbene. A series of transition-metal catalysts, including CuI, AuCl, AuPPh3Cl, [Rh(cod)Cl]2, and [RuCl2(p-cymene)]2, were examined (Table 1, entries 1−5). [RuCl2(p-cymene)]2 showed the Table 1. . Optimization of the Reaction Conditions

a

entry

solvent

1a/2a

cat.

yielda (%)

E/Zb

1 2 3d 4 5 6 7 8 9 10e 11g

MeCN MeCN MeCN PhMe PhMe PhMe PhMe PhMe PhMe THF THF

1:1 1:1 1:1 1:1 1:1 1:1 1:1 1:1 1:1 1.3:1 1.3:1

CuI AuCl AuPPh3Cl [Rh(cod)Cl]2 [RuCl2(p-cymene)]2 Ru(PPh3)3Cl2 CpRu(PPh3)2Cl [RuCl2(benzene)]2 [Cp*Ru(cod)Cl] [Cp*Ru(cod)Cl] none

10 19 21 12 43 19 21 37 72 98 (88f) 0

ndc nd nd nd 3:1 4:1 10:1 2.5:1 3:1 5:1

Reaction conditions: 1a−f (0.26 mmol), 2a (0.20 mmol), and [Cp*Ru(cod)Cl] (2.5 mol %) in THF (1.0 mL) at 60 °C. All of the yields refer to the isolated products by column chromatography. The ratio of E/Z was determined by 1H NMR (400 MHz). bThe reaction time was 12 h, and 1.5 equiv of cyclopropene was used.

on the aromatic ring of the aryl diazoacetates did not significantly affect the reaction, except that strong electronwithdrawing substituents reduce the yields (3l,m). The steric effects at the ortho position of the aromatic ring had a negative effect on the results. The substrate bearing a fluoro substituent at the ortho position gave the corresponding product 3k in 58% yield, while the sterically bulkier ortho chloro substituent completely shut down the reaction (3t). Moreover, the reaction with diazo compounds bearing an alkyl group also proceeded, affording the corresponding products in good yields (3q,s). However, the stereoselectivity of the reaction was rather poor in these cases. Finally, the reaction with diazo substrate bearing two ester groups also worked well to give product in 82% yield. We have proposed two possible reaction pathways for this formal carbene dimerization reaction (Scheme 4, paths a and b). The major difference between these two pathways is which substrate, cyclopropene or diazo compound, first reacts with the catalyst to generate the corresponding Ru(II) carbene species. To gain insight into the reaction mechanism, in particular the differentiation of the two possible pathways, some mechanistic experiments were carried out. First, pairwise competition experiments of 2a/2g and 2a/2b under the standard conditions were carried out. The ratios of the products clearly demonstrate that the diazo compounds bearing electron-donating substituents on the aromatic ring are more reactive (Scheme 5). The results imply that the diazo substrate likely functions as a nucleophile in the reaction, which is in accordance with path b as shown in Scheme 4. Subsequently, the starting materials, the diazo compound and the cyclopropene, were treated separately under the standard conditions (Scheme 6). Both cyclopropene 1a and diazo compound 2a could react under Ru(II) catalysis, resulting in the formation of self-dimerization products 4 and 5 in 42% and 43% yield, respectively. The results suggest that the formation of Ru(II) carbene from cyclopropene or diazo compound occurs at a similar rate. However, the diazo compound bearing two ester groups 2m remained unchanged under Ru(II) catalysis. Thus, in the case of Ru(II)-catalyzed

a

NMR yield. bDetermined by 1H NMR (400 MHz). cnd: not determined. d5 mol % of AgOTf was used. e2.5 mol % of catalyst was used. fIsolated yield. gThe substrates remained unchanged.

highest efficiency among these catalysts (entry 5). Consequently, we proceeded to further examine other Ru(II) catalysts (entries 6−9), and it was found that [Cp*Ru(cod)Cl] (Cp* = C5Me5) afforded the optimal results (entry 9). Furthermore, changing the solvent from toluene to THF and slightly increasing the amount of cyclopropene 1a could further improve the yield. Under the optimized conditions, 3a could be isolated in 88% yield with an E/Z of 5:1 (Table 1). Finally, a control experiment was carried out in the absence of the catalyst. No reaction occurred under such conditions (entry 11). With the optimized reaction conditions, the scope of cyclopropenes was then examined. As illustrated in Scheme 2, various 3,3-disubstituted cyclopropenes reacted smoothly with methyl 2-diazo-2-phenylacetate 2a to afford the corresponding products in moderate to good yields. However, the stereoselectivity of these cyclopropenes was not satisfactory except for the reaction with 3,3-diphenylcyclopropene. Isomers of the product (3d and 3d′), which bear an adamantly substituent, can be separated by column chromatography, while all of the other products were inseparable mixtures. The configurations of these two isomers were confirmed by NOESY spectra, confirming that the E,E isomer is the major product. By comparing the products’ NMR spectra, we assume that in all the cases the E isomers are the major products. Next, the scope of diazo substrates was examined with a series of diazo esters. As shown in Scheme 3, the substituents 1027

DOI: 10.1021/acs.joc.7b02634 J. Org. Chem. 2018, 83, 1026−1032

Note

The Journal of Organic Chemistry Scheme 3. Scope of the Diazo Compoundsa

products. It is thus suspected that the alkenyl moieties may hamper the reaction. In order to confirm the effect of alkenyl moiety on the reaction, the Ru(II)-catalyzed reactions were carried out in the presence of additional alkenes (Scheme 7). Cyclohexene was found to slow the reaction, while 1-dodecene completely shut down the reaction. The negative effect of alkene to the cross-coupling reaction may be attributed to the relatively strong coordination effect of the alkene with the Ru(II) catalyst, thus preventing the interaction of cyclopropene or diazo substrate with the catalyst. On the basis of the experimental observation, a plausible mechanism was proposed as depicted in Scheme 8. First, Ru(II) catalyst reacts with cyclopropene A to generate a coordination complex B. In the presence of olefin, the olefin bonds to [Cp*Ru(cod)Cl] to form relatively stable complex C, thus competing the complexation with cyclopropene substrate. From complex B, ring opening of cyclopropene leads to the formation of vinyl Ru(II) carbene intermediate D. Nucleophilic addition of diazo compound E to Ru(II) carbene intermediate D generates the adduct F. Subsequently, dinitrogen extrusion affords the final product G, with regeneration of the Ru(II) catalyst. In summary, a new type of Ru(II)-catalyzed carbene dimerization of cyclopropenes and diazo compounds has been developed. A series of cyclopropenes and diazo compounds were tolerated in this formal carbene dimerization, and the corresponding 1,3-butadiene products could be obtained in moderate to good yields. Notably, homocoupling products were not observed, suggesting the high selectivity of the substrates toward Ru(II) catalysts. The results indicate that carbene dimerization between two different carbene precursors can be a general strategy for the construction of double bonds. Finally, it is also a demonstration of novel application of the vinyl metal carbenes that are generated in situ from cyclopropenes.

■

a

Reaction conditions: 1a,c,d (0.26 mmol), 2b−n (0.20 mmol), and [Cp*Ru(cod)Cl] (2.5 mol %) in THF (1.0 mL) at 60 °C. All of the yields refer to the isolated products by column chromatography. The ratio of E/Z was determined by 1H NMR. bThe reaction temperature was 70 °C. c2.0 equiv of cyclopropene was used. dThe reaction was carried out in PhMe (1.0 mL) at 50 °C. eThe yield was estimated by 1 H NMR (400 MHz). fReaction conditions: 1d (0.2 mmol), 2l (0.4 mmol), and [Cp*Ru(cod)Cl] (2.5 mol %) in PhMe (0.4 mL) at 60 °C.

EXPERIMENTAL SECTION

General Methods. Air- and moisture-sensitive reactions were carried out in oven-dried glassware sealed with rubber septa under nitrogen atmosphere. THF and PhMe were distilled from sodium with benzophenone as indicator. [Cp*Ru(cod)Cl] and other metal salts were commercially available. Purification of products was accomplished by flash chromatography on silica gel (200−300 mesh, from Qingdao, China). NMR spectra were measured on a Bruker ARX400 (1H at 400 MHz, 13C at 100 MHz) magnetic resonance spectrometer. Chemical shifts are reported in ppm using tetramethylsilane as internal standard (s = singlet, d = doublet, t = triplet, q = quartet, dd = doublet of doublets, m = multiplet). IR spectra were recorded on a Nicolet Avatar 330 Fourier transform spectrometer (FT-IR) and are reported in wave numbers (cm−1). For HRMS measurements, the mass analyzer is FT-ICR. PE: petroleum ether. EA: ethyl acetate. Preparation of Cyclopropenes. Cyclopropenes 1a, 1b, 1c, 1d, 1e, and 1f are known compounds and were prepared via literature procedures.9d General Procedure for the Ru(II)-Catalyzed Reactions. A 10 mL oven-dried Schlenk flask was charged with [Cp*Ru(cod)Cl] (1.9 mg, 0.005 mmol, 2.5 mol %) under nitrogen. Then dry THF (1.0 mL) was added using a syringe. Cyclopropene (0.26 mmol, 1.3 equiv) and diazo compound (0.20 mmol, 1.0 equiv) were successively added by syringe. The reaction was heated at 60 °C while maintaining stirring for 4 h, and then the reaction mixture was cooled to room temperature. The reaction mixture was filtered through a short column of silica gel eluted by chloroform. The solvent was then removed in vacuo to leave a crude mixture, which was purified by silica gel column chromatography to afford pure products.

Scheme 4. Proposed Reaction Pathways

reaction of 2m and 1d to give 3r, it is unambiguous that cyclopropene 1d first reacts with Ru(II) catalyst to generate vinyl Ru(II) carbene intermediate. While examining the scope of diazo compounds, it was found that diazo compounds bearing an alkenyl group gave no 1028

DOI: 10.1021/acs.joc.7b02634 J. Org. Chem. 2018, 83, 1026−1032

Note

The Journal of Organic Chemistry Scheme 5. Competition Experiments of the Diazo Compounds

Scheme 6. Control Experiments

Scheme 8. Proposed Reaction Mechanism

Scheme 7. Effect of Alkenyl Groups on the Reaction

25.2H), 7.20−7.22 (m, 6.3H), 6.96 (d, J = 11.8 Hz, 1H), 6.63 (d, J = 11.8 Hz, 1H), 3.82 (s, 3H), 3.75 (s, 5.3H), 2.32 (t, J = 7.4 Hz, 10.6H), 2.26 (t, J = 7.5 Hz, 2H), 2.17 (t, J = 7.5 Hz, 2H), 2.03 (t, J = 7.4 Hz, 10.6H), 1.20−1.46 (m, 118H), 0.84−0.92 (m, 42H); 13C NMR (100 MHz, CDCl3) δ 168.5, 155.3, 153.5, 138.8, 136.7, 135.5, 134.0, 130.3, 130.0, 129.6, 128.2, 127.8, 127.6, 127.38, 127.33, 121.5, 121.3, 52.0, 38.2, 37.9, 31.7, 31.6, 31.6, 31.2, 29.4, 29.3, 29.2, 29.1, 29.0, 28.2, 27.9, 22.6, 14.11, 14.07; HRMS (EI, m/z) calcd for C24H36O2 [M]+ 356.2710, found 356.2712; IR (film) 2955, 1713, 1623, 1461, 1433, 1242, 1194, 1139 cm−1. Methyl 5,5-dicyclohexyl-2-phenylpenta-2,4-dienoate (3b). colorless oil; yield 47.2 mg, (67%); E/Z = 8:1; Rf = 0.52 (PE/EA = 30:1); 1 H NMR (400 MHz, CDCl3) δ 7.93 (d, J = 12.0 Hz, 7.6H), 7.30−7.40 (m, 25.8H), 7.20−7.23 (m, 17.2H), 7.11 (d, J = 11.9 Hz, 1H), 6.70 (d, J = 12.0 Hz, 1H), 5.86 (d, J = 12.0 Hz, 7.6H), 3.82 (s, 3H), 3.76 (s, 22.8H), 2.68−2.85 (m, 8.6H), 1.97−2.08 (m, 8.6H), 0.90−1.80 (m, 172H); 13C NMR (100 MHz, CDCl3) δ 168.6, 168.5, 164.5, 162.9, 139.1, 136.4, 135.4, 134.4, 130.4, 129.7, 129.5, 128.2, 127.7, 127.3, 119.3, 119.0, 52.0, 51.7, 41.7, 41.5, 41.2, 34.3, 33.9, 30.9, 29.7, 26.9, 26.7, 26.4, 26.3, 26.1, 26.0, 25.9; HRMS (EI, m/z) calcd for C24H32O2

The reactions of 2l and 2n were carried in PhMe (1.0 mL) at 50 °C. The reactions of 1d (0.20 mmol, 1.0 equiv) and 2m (0.40 mmol, 2,0 equiv) were carried out in PhMe (0.4 mL) Methyl 5-hexyl-2-phenylundeca-2,4-dienoate (3a): colorless oil; yield 63.0 mg (88%); E/Z = 5:1; Rf = 0.55 (PE/EA = 30:1); 1H NMR (400 MHz, CDCl3) δ 7.78 (d, J = 12.0 Hz, 5.3H), 7.28−7.39 (m, 1029

DOI: 10.1021/acs.joc.7b02634 J. Org. Chem. 2018, 83, 1026−1032

Note

The Journal of Organic Chemistry [M]+ 352.2397, found 352.2397; IR (film) 2957, 1706, 1629, 1466, 1254, 1175 cm−1. Methyl (E)-2,5,5-triphenylpenta-2,4-dienoate (3c): 11 yellow solid (mp = 142−145 °C); yield 57.9 mg (85%); E/Z > 20:1; Rf = 0.38 (PE/EA = 30:1); 1H NMR (400 MHz, CDCl3) δ 7.55 (d, J = 11.8 Hz, 1H), 7.31−7.46 (m, 7H), 7.14−7.27 (m, 8H), 6.67 (d, J = 11.8 Hz, 1H), 3.69 (s, 3H); 13C NMR (100 MHz, CDCl3) δ 168.1, 150.9, 141.6, 138.9, 138.1, 135.3, 133.2, 130.6, 130.4, 128.5, 128.3, 128.2, 128.2, 128.0, 127.7, 123.7, 52.1. Methyl (2E,4E)-5-((3r,5r,7r)-adamantan-1-yl)-2-phenylhexa-2,4dienoate (3d): white solid (mp = 118−121 °C); yield 28.8 mg (43%); Rf = 0.46 (PE/EA = 20:1); 1H NMR (400 MHz, CDCl3) δ 7.84 (d, J = 11.8 Hz, 1H), 7.22−7.40 (m, 5H), 5.96 (d, J = 11.8 Hz, 1H), 3.75 (s, 3H), 1.92−1.96 (m, 6H), 1.57−1.70 (m, 12H); 13C NMR (100 MHz, CDCl3) δ 168.5, 158.0, 137.6, 135.6, 130.3, 130.3, 127.9, 127.4, 118.4, 52.0, 40.4, 39.2, 36.8, 28.5, 13.2; HRMS (EI, m/z) calcd for C23H29O2 [M + H]+ 337.2162, found 337.2156; IR (film) 2903, 1710, 1616, 1433, 1244, 1208 cm−1. Methyl (2Z,4E)-5-((3r,5r,7r)-adamantan-1-yl)-2-phenylhexa-2,4dienoate (3d′): white solid (mp = 119−122 °C); yield 12.6 mg (19%); Rf = 0.49 (PE/EA = 20:1); 1H NMR (400 MHz, CDCl3) δ 7.28−7.35 (m, 5H), 7.02 (d, J = 11.6 Hz, 1H), 6.75 (d, J = 11.6 Hz, 1H), 3.83 (s, 3H), 2.05 (s, 3H), 1.86 (s, 3H), 1.66−1.74 (m, 12H); 13 C NMR (100 MHz, CDCl3) δ 168.6, 156.3, 139.1, 135.5, 130.7, 128.2, 127.8, 127.4, 118.8, 51.8, 40.6, 39.2, 36.9, 28.6, 12.6; HRMS (EI, m/z) calcd for C23H29O2 [M + H]+ 337.2162, found 337.2156; IR (film) 2905, 1712, 1617, 1449, 1433, 1202 cm−1. Methyl (E)-4-cyclooctylidene-2-phenylbut-2-enoate (3e): colorless oil; yield 33.0 mg (58%); E/Z = 4:1; Rf = 0.51 (PE/EA = 30:1); 1H NMR (400 MHz, CDCl3) δ 7.80 (d, J = 12.1 Hz, 4.1H), 7.28−7.40 (m, 15.3H), 7.20−7.23 (m, 10.2H), 6.98 (d, J = 12.0 Hz, 1H), 6.67 (d, J = 12.0 Hz, 1H), 5.90 (d, J = 12.1 Hz, 4.1H), 3.82 (s, 3H), 3.75 (s, 12.3H), 2.52 (t, J = 6.2 Hz, 8.2H), 2.45 (t, J = 6.2 Hz, 2H), 2.36 (t, J = 5.9 Hz, 2H), 2.20 (t, J = 6.0 Hz, 8.2H), 1.62−1.80 (m, 20.4H), 1.46− 1.52 (m, 30.6H); 13C NMR (100 MHz, CDCl3) δ 168.5, 157.8, 155.7, 138.9, 136.6, 135.6, 134.1, 130.4, 129.1, 128.2, 127.8, 127.6, 127.3, 127.3, 122.2, 121.8, 52.0, 51.7, 38.7, 38.4, 29.9, 29.7, 29.4, 28.7, 28.5, 27.6, 27.4, 26.3, 26.2, 25.8, 25.64, 25.60; HRMS (EI, m/z) calcd for C19H24O2 [M]+ 284.1771, found 284.1771; IR (film) 2927, 1710, 1615, 1433, 1242, 1201, 1136 cm−1. Methyl (E)-4-cyclododecylidene-2-phenylbut-2-enoate (3f): colorless oil; yield 51.1 mg (75%); E/Z = 5:1; Rf = 0.50 (PE/EA = 30:1); 1 H NMR (400 MHz, CDCl3) δ 7.82 (d, J = 11.9 Hz, 5.0H), 7.28−7.39 (m, 18.0H), 7.21−7.23 (m, 12.0H), 7.02 (d, J = 11.8 Hz, 1H), 6.76 (d, J = 11.7 Hz, 1H), 5.97 (d, J = 11.9 Hz, 5.0H), 3.81 (s, 3H), 3.76 (s, 15.0H), 2.39 (t, J = 6.7 Hz, 10.0H), 2.32 (t, J = 6.7 Hz, 2H), 2.25 (t, J = 6.7 Hz, 2H), 2.13 (t, J = 6.7 Hz, 10.0H), 1.21−1.69 (m, 108H); 13C NMR (100 MHz, CDCl3) δ 168.6, 168.5, 153.4, 151.5, 138.8, 136.8, 135.5, 134.2, 130.4, 130.0, 129.8, 128.2, 127.8, 127.6, 127.3, 122.5, 122.3, 52.0, 51.7, 32.9, 32.8, 30.0, 29.4, 25.05, 25.00, 24.9, 24.3, 24.25, 24.21, 24.0, 23.9, 23.3, 23.1, 23.0, 22.2; HRMS (EI, m/z) calcd for C23H32O2 [M]+ 340.2397, found 340.2398; IR (film) 2934, 1712, 1624, 1469, 1433, 1245, 1195 cm−1. Methyl 5-hexyl-2-(4-methoxyphenyl)undeca-2,4-dienoate (3g): yellow oil; yield 58.8 mg, (76%); E/Z = 5:1; Rf = 0.45 (PE/EA = 30:1); 1H NMR (400 MHz, CDCl3) δ 7.74 (d, J = 11.9 Hz, 2.5H), 7.26−7.28 (m, 2H), 7.14−7.16 (m, 5.0H), 6.86−6.92 (m, 8.0H), 6.58 (d, J = 11.8 Hz, 1H), 5.89 (d, J = 11.9 Hz, 2.5H), 3.83 (s, 7.5H), 3.82 (s, 3H), 3.81 (s, 3H), 3.75 (s, 7.5H), 2.31 (t, J = 7.7 Hz, 5.0H), 2.25 (t, J = 7.7 Hz, 2H), 2.16 (t, J = 7.6 Hz, 2H), 2.04 (t, J = 7.5 Hz, 5.0H), 1.21−1.46 (m, 70H), 0.84−0.92 (m, 21H); 13C NMR (100 MHz, CDCl3) δ 168.9, 168.8, 159.1, 158.8, 154,8, 152.5, 136.4, 132.6, 131.6, 131.3, 129.6, 129.2, 128.8, 127.8, 121.6, 113.7, 113.3, 55.3, 55.2, 52.0, 51.7, 38.2, 38.0, 31.8, 31.7, 31.6, 31.3, 30.9, 29.3, 29.3, 29.2, 29.0, 28.2, 28.0, 22.6, 14.1; HRMS (EI, m/z) calcd for C25H38O3 [M]+ 386.2816, found 386.2812; IR (film) 2955, 1712, 1644, 1512, 1464, 1427, 1246 cm−1. Methyl 2-([1,1′-biphenyl]-4-yl)-5-hexylundeca-2,4-dienoate (3h): colorless oil; yield 73.5 mg (85%); E/Z = 4:1; Rf = 0.46 (PE/EA = 30:1); 1H NMR (400 MHz, CDCl3) δ 7.80 (d, J = 12.0 Hz, 3.6H),

7.56−7.65 (m, 23.5H), 7.41−7.46 (m, 9.2H), 7.29−7.37 (m, 9.2H), 7.02 (d, J = 11.8 Hz, 1H), 6.64 (d, J = 11.8 Hz, 1H), 5.94 (d, J = 12.0 Hz, 3.6H), 3.85 (s, 3H), 3.78 (s, 10.8H), 2.34 (t, J = 7.7 Hz, 7.2H), 2.28 (t, J = 7.7 Hz, 2H), 2.18 (t, J = 7.5 Hz, 2H), 2.06 (t, J = 7.5 Hz, 7.2H), 1.22−1.48 (m, 92H), 0.83−0.93 (m, 27.6H); 13C NMR (100 MHz, CDCl3) δ 168.6, 168.5, 155.6, 153.7, 140.9, 140.7, 140.2, 140.1, 137.8, 136.9, 134.6, 134.0, 130.8, 129.6, 129.2, 128.8, 128.0, 127.4, 127.3, 127.1, 127.0, 126.6, 121.6, 121.4, 52.1, 51.8, 38.3, 38.0, 31.8, 31.70, 31.66, 31.3, 31.0, 29.5, 29.4, 29.2, 29.1, 29.0, 28.2, 28.0, 22.6, 14.12, 14.08; HRMS (EI, m/z) calcd for C30H40O2 [M]+ 432.3023, found 432.3022; IR (film) 2958, 1712, 1623, 1487, 1466, 1434, 1242 cm−1. Methyl 2-(4-chlorophenyl)-5-hexylundeca-2,4-dienoate (3i): colorless oil; yield 67.3 mg, 86%; E/Z = 5:1; Rf = 0.51 (PE/EA = 30:1); 1 H NMR (400 MHz, CDCl3) δ 7.78 (d, J = 12.0 Hz, 4.8H), 7.25−7.35 (m, 11.6H), 7.14−7.16 (m, 11.6H), 6.93 (d, J = 11.8 Hz, 1H), 6.66 (d, J = 11.9 Hz, 1H), 5.81 (d, J = 12.0 Hz, 4.8H), 3.82 (s, 3H), 3.75 (s, 14.2H), 2.32 (t, J = 7.7 Hz, 9.6H), 2.25 (t, J = 7.7 Hz, 2H), 2.17 (t, J = 7.6 Hz, 2H), 2.05 (t, J = 7.4 Hz, 9.6H), 1.21−1.46 (m, 116H), 0.84− 0.90 (m, 34.8H); 13C NMR (100 MHz, CDCl3) δ 168.1, 158.3, 154.5, 137.5, 137.2, 135.0, 134.0, 133.3,131.8, 129.1, 128.6, 128.4, 128.3, 128.1, 121.0, 52.1, 51.8, 38.3, 38.0, 31.8, 31.7, 31.6, 31.3, 30.9, 29.41, 29.36, 29.2, 29.1, 29.0, 28.2, 28.0, 22.6, 14.11, 14.07; HRMS (EI, m/z) calcd for C24H35ClO2 [M]+ 390.2320, found 390.2320; IR (film) 2954, 1713, 1623, 1462, 1434, 1242, 1201 cm−1. Methyl 2-(4-bromophenyl)-5-hexylundeca-2,4-dienoate (3j): colorless oil; yield 84.5 mg (97%); E/Z = 7:1; Rf = 0.51 (PE/EA = 30:1); 1 H NMR (400 MHz, CDCl3) δ 7.78 (d, J = 12.0 Hz, 6.8H), 7.48−7.51 (m, 13.6H), 7.45−7.47 (m, 2H), 7.19−7.22 (m, 2H), 7.08−7.10 (m, 13.6H), 6.94 (d, J = 11.8 Hz, 1H), 6.68 (d, J = 11.8 Hz, 1H), 5.81 (d, J = 12.0 Hz, 6.8H), 3.81 (s, 3H), 3.76 (s, 20.4H), 2.32 (t, J = 7.7 Hz, 13.6H), 2.25 (t, J = 7.7 Hz, 2H), 2.17 ((t, J = 7.6 Hz, 2H), 2.05 (t, J = 7.5 Hz, 13.6H), 1.21−1.46 (m, 156H), 0.85−0.92 (m, 46.8H); 13C NMR (100 MHz, CDCl3) δ 168.0, 156.4, 154.6, 138.0, 137.2, 135.1, 134.5, 132.1, 131.4, 130.1, 129.3, 128.6, 128.3, 121.5, 121.4, 121.0, 52.1, 51.8, 38.3, 38.0, 31.8, 31.7, 31.6, 31.3, 31.0, 29.7, 29.4, 29.3, 29.2, 29.1, 29.0, 28.2, 28.0, 22.6, 14.1; HRMS (EI, m/z) calcd for C24H35BrO2 [M]+ 434.1815, found 434.1816; IR (film) 2954, 1713, 1612, 1487, 1434, 1242 cm−1. Ethyl 2-(2-fluorophenyl)-5-hexylundeca-2,4-dienoate (3k): colorless oil; yield 43.4 mg (58%); E/Z > 20:1; Rf = 0.53 (PE/EA = 30:1); 1 H NMR (400 MHz, CDCl3) δ 7.84 (d, J = 12.0 Hz, 1H), 7.28−7.36 (m, 1H), 7.06−7.09 (m, 3H), 5.78 (d, J = 12.0 Hz, 1H), 4.22 (q, J = 7.10 Hz, 2H), 2.33 (t, J = 7.7 Hz, 2H), 2.05 (t, J = 7.5 Hz, 2H), 1.20− 1.47 (m, 20H), 0.84−0.92 (m, 6H); 13C NMR (100 MHz, CDCl3) δ 167.2, 161.5, 159.0, 156.1, 137.9, 132.4 (d, J = 3.5 Hz), 129.4 (d, J = 8.1 Hz), 124.1, 123.5 (dd, J = 6.4 Hz, J = 10.0 Hz), 121.1, 115.4 (d, J = 22 Hz), 60.8, 38.0, 31.6, 31.3, 29.3, 29.0, 28.9, 27.9, 22.6, 14.3, 14.1; HRMS (EI, m/z) calcd for C25H37FO2 [M]+ 388.2773, found 388.2771; IR (film) 2959, 1712, 1625, 1491, 1453, 1244, 1221, 1178, 1139 cm−1. Ethyl 4-(5-hexyl-1-methoxy-1-oxoundeca-2,4-dien-2-yl)benzoate (3l): colorless oil; yield 55.6 mg (67%); E/Z = 6:1; Rf = 0.50 (PE/EA = 5:1); 1H NMR (400 MHz, CDCl3) δ 7.91−8.04 (m, 13.6H), 7.81 (d, J = 12 Hz, 5.8H), 7.39−7.55 (m, 13.6H), 7.00 (d, J = 11.8 Hz, 1H), 6.69 (d, J = 11.8 Hz, 1H), 5.77 (d, J = 12 Hz, 5.8H), 4.32 (q, J = 7.1 Hz, 2H), 4.23 (q, J = 7.1 Hz, 11.6H), 3.92 (s, 3H), 3.91 (s, 17.4H), 2.32 (t, J = 7.7 Hz, 11.6H), 2.27 (t, J = 7.8 Hz, 2H), 2.18 (t, J = 7.5 Hz, 2H), 2.03 (t, J = 7.4 Hz, 11.6H), 1.19−1.47 (m, 134H), 0.83−0.93 (m, 41.6H); 13C NMR (100 MHz, CDCl3) δ 167.7, 167.6, 167.0, 166.9, 156.0, 154.2, 139.3, 136.9, 136.0, 134.9, 134.6, 132.1, 131.6, 130.2, 129.8, 129.2, 128.8, 128.4, 128.3, 128.2, 127.9, 121.4, 120.9, 60.8, 52.1, 52.0, 38.2, 38.0, 31.8, 31.7, 31.6, 31.3, 30.9, 29.7, 29.4, 29.3, 29.1, 29.0, 28.9, 28.1, 27.9, 22.6, 22.5, 14.2, 14.09, 14.05; HRMS (EI, m/z) calcd for C27H40O4 [M]+ 428.2921, found 428.2923; IR (film) 2953, 1726, 1709, 1622, 1464, 1440, 1269, 1240 cm−1. Ethyl 5-hexyl-2-(4-nitrophenyl)undeca-2,4-dienoate (3m): yellow oil; yield 39.0 mg (47%); E/Z = 10:1; Rf = 0.40 (PE/EA = 30:1); 1H NMR (400 MHz, CDCl3) δ 8.23 (d, J = 8.6 Hz, 22H), 8.19 (d, J = 8.8 Hz, 2H), 7.85 (d, J = 12.1 Hz, 11H), 7.50 (d, J = 8.7 Hz, 2H), 7.40 (d, 1030

DOI: 10.1021/acs.joc.7b02634 J. Org. Chem. 2018, 83, 1026−1032

Note

The Journal of Organic Chemistry

+ H]+ 365.2475, found 365.2469; IR (film) 2905, 1703, 1623, 1452, 1257, 1190, 1082 cm−1. Competition Experiments of the Diazo Compounds. A 10 mL oven-dried Schlenk flask was charged with [Cp*Ru(cod)Cl] (1.0 mg, 0.0025 mmol, 2.5 mol %) under nitrogen. Then dry THF (0.3 mL) was added using a syringe. Cyclopropene (1a, 0.13 mmol, 1.3 equiv) and diazo compounds (2a, 0.05 mmol, and 2g, 0.05 mmol, dissolved in 0.2 mL of THF) were successively added by syringe. The reaction was heated at 60 °C with stirring for 0.5 min and then cooled to 0 °C immediately. The reaction mixture was filtered through a short column of silica gel eluted with chloroform. Solvent was then removed in vacuo to leave a crude mixture. The ratio of the products was determined by 1H NMR (400 MHz). Control Experiments. A 10 mL oven-dried Schlenk flask was charged with [Cp*Ru(cod)Cl] (1.0 mg, 0.0025 mmol, 2.5 mol %) under nitrogen. Then dry THF (0.5 mL) was added using a syringe. Substrate (1d, 2a, or 2m, 0.1 mmol) was successively added by syringe. The reaction was heated at 60 °C with stirring for 4 h and then cooled to room temperature. The reaction mixture was filtered through a short column of silica gel, eluted with chloroform. Solvent was then removed in vacuo to leave a crude mixture. The ratio of the products was determined by 1H NMR (400 MHz). Effect of Alkenyl Groups on the Reaction. A 10 mL oven-dried Schlenk flask was charged with [Cp*Ru(cod)Cl] (1.0 mg, 0.005 mmol, 2.5 mol %) under nitrogen. Then dry THF (0.3 mL) was added using a syringe. Cyclopropene 1a (0.13 mmol, 1.3 equiv) and the olefin additive (0.13 mmol) were dissolved in THF (0.2 mL), and the solution and diazo compound (0.20 mmol, 1.0 equiv) were successively added by syringe. The reaction was heated at 60 °C with stirring for 2 min or 4 h and then cooled to room temperature immediately. The reaction mixture was filtered through a short column of silica gel, eluted with chloroform. Solvent was then removed in vacuo to leave a crude mixture. The yield was determined by 1H NMR (400 MHz).

J = 8.6 Hz, 22H), 7.05 (d, J = 12.0 Hz, 1H), 6.72 (d, J = 11.7 Hz), 5.78 (d, J = 12.1 Hz, 11H), 4.34 (q, J = 7.1 Hz, 2H), 4.24 (q, J = 7.1 Hz, 22H), 2.34 (t, J = 7.7 Hz, 22H), 2.29 (t, J = 8.0 Hz, 2H), 2.20 (t, J = 7.8 Hz, 2H), 2.06 (t, J = 7.5 Hz, 22H), 1.21−1.52 (m, 246.6H), 0.84− 0.92 (m, 66.3H); 13C NMR (100 MHz, CDCl3) δ 166.9, 158.0, 147.0, 142.8, 137.9,136.5,131.5, 128.3, 128.1, 127.6, 123,5, 123.1, 121.4, 120.5, 61.0, 38.2, 31.6, 31.4, 29.3, 29.1, 29.0, 28.0, 22.6, 14.3, 14.1, 14.0; HRMS (EI, m/z) calcd for C25H37NO4 [M]+ 415.2717, found 415.2716; IR (film) 2957, 1709, 1621, 1601, 1346, 1241, 1187 cm−1. Methyl (E)-5,5-diphenyl-2-(p-tolyl)penta-2,4-dienoate (3n): white solid (mp = 148−152 °C); yield 61.6 mg (87%); E/Z > 20:1; Rf = 0.20 (PE/EA = 30:1); 1H NMR (400 MHz, CDCl3) δ 7.52 (d, J = 11.8 Hz, 1H), 7.39−7.46 (m 3H), 7.16−7.28 (m, 12H), 6.71 (d, J = 11.8 Hz, 1H), 3.70 (s, 3H), 2.39(s, 3H); 13C NMR (100 MHz, CDCl3) δ 168.3, 150.6, 141.8, 139.0, 137.9, 137.6, 133.2, 132.3, 130.6, 130.3, 128.8, 128.4, 128.3, 128.3, 128.3, 128.3, 124.0, 52.1, 21.4; HRMS (ESI, m/z) calcd for C25H23O2 [M + H]+ 355.1693, found 355.1689; IR (film) 2951.6, 1708.6, 1261.0, 1234.1 cm−1. Methyl (E)-5,5-diphenyl-2-(4-(trifluoromethyl)phenyl)penta-2,4dienoate (3o): white solid (mp = 108−110 °C); yield 58.1 mg, 71%; E/Z > 20:1; Rf = 0.23 (PE/EA = 30:1); 1H NMR (400 MHz, CDCl3) δ 7.67 (d, J = 8.1 Hz, 2H), 7.61 (d, J = 11.9 Hz, 1H), 7.44− 7.46 (m, 5H), 7.25−7.28 (m, 5H), 7.15−7.18 (m, 2H), 6.60 (d, J = 11.9 Hz, 1H), 3.71 (s, 3H); 13C NMR (100 MHz, CDCl3) δ 167.5, 152.4, 141.4, 139.2, 138.7, 131.6, 130.8, 130.6, 129.80 (q, J = 32.2 Hz), 128.9, 128.6, 128.4, 128.4, 28.3, 128.1 (q, J = 3.7 Hz), 124.2 (q, J = 272.1 Hz), 122.9, 52.2; HRMS (ESI, m/z) calcd for C25H20F3O2 [M + H]+ 409.1410, found 409.1400; IR (film) 2918, 1709, 1433, 1324, 1264, 1236, 1165 cm−1. 2-Methoxy-2-oxoethyl 5-hexyl-2-phenylundeca-2,4-dienoate (3p): colorless oil; yield 66.3 mg (80%); E/Z > 20:1; Rf = 0.40 (PE/EA = 5:1); 1H NMR (400 MHz, CDCl3) δ 7.86 (d, J = 12.0 Hz, 3.4H), 7.27−7.46 (m, 22.0H), 7.04 (d, J = 11.9 Hz, 1.0H), 6.78 (d, J = 11.9 Hz, 1.0H), 5.91 (d, J = 12.0 Hz, 3.4H), 4.75 (s, 2H), 4.69 (s, 6.8 H), 3.80 (s, 3H), 3.77 (s, 10.2H), 2.33 (t, J = 7.7 Hz, 6.8H), 2.27 (t, J = 7.7 Hz, 2H), 2.18 (t, J = 7.5 Hz, 2H), 2.05 (t, J = 7.4 Hz, 6.9H), 1.20−1.45 (m, 80H), 0.84−0.92 (m, 17H); 13C NMR (100 MHz, CDCl3) δ 168.6, 168.3, 167.4, 167.2, 156.4, 154.6, 138.7, 138.0, 136.0, 135.1, 130.5, 128.7, 128.6, 128.1, 128.0, 127.9, 127.5, 121.7, 121.4, 61.0, 60.8, 52.4, 51.2, 38.3, 38.0, 31.8, 31.7, 31.6, 31.4, 31.0, 29.7, 29.44, 29.40, 29.2, 29.1, 29.0, 28.2, 28.0, 22.6, 14.1; HRMS (EI, m/z) calcd for C26H38O4 [M]+ 414.2765, found 414.2765; IR (film) 2953, 1767, 1717, 1621, 1462, 1378, 1203, 1116 cm−1. Ethyl (E)-2-((E)-3-((3r,5r,7r)-adamantan-1-yl)but-2-en-1-ylidene)decanoate (3q): colorless oil; yield 41.7 mg (54%); Rf = 0.47 (PE/EA = 20:1); 1H NMR (400 MHz, CDCl3) δ 7.53 (d, J = 11.7 Hz, 1H), 6.16 (d, J = 11.8 Hz, 1H), 4.21 (q, J = 7.1 Hz, 2H), 2.39−2.43 (m, 2H), 2.04 (s, 3H), 1.86 (s, 3H), 1.66−1.76 (m, 12H), 1.27−1.32 (m, 15H), 0.88 (t, J = 6.7 Hz, 3H); 13C NMR (100 MHz, CDCl3) δ 168.8, 155.8, 135.0, 117.1, 60.2, 40.6, 39.1, 36.9, 31.9, 29.5, 29.4, 29.4, 29.3, 28.6, 26.6, 22.7, 14.4, 14.2, 13.0; HRMS (ESI, m/z) calcd for C26H43O2 [M + H]+ 387.3258, found 387.3249; IR (film) 2916, 1703, 1624, 1452, 1255, 1123, cm−1. Dimethyl 2-((E)-3-((3r,5r,7r)-adamantan-1-yl)but-2-en-1ylidene)malonate (3r). white solid (mp = 71−74 °C); yield 52.2 mg (82%); Rf = 0.42 (PE/EA = 10:1); 1H NMR (400 MHz, CDCl3) δ 7.80 (d, J = 12.1 Hz, 1H), 6.36 (d, J = 12.1 Hz, 1H), 3.86 (s, 3H), 3.80 (s, 3H), 2.04 (s, 3H), 1.93 (s, 3H), 1.65−1.76 (m, 12H); 13C NMR (100 MHz, CDCl3) δ 166.4, 165.6, 163.7, 142.3, 122.7, 117.3, 52.3, 52.2, 40.3, 39.7, 36.7, 28.4, 13.3; HRMS (ESI, m/z) calcd for C19H27O4 [M + H]+ 319.1904, found 319.1898; IR (film) 2905, 1719, 1616, 1435, 1384, 1255, 1213, 1151 cm−1. Ethyl (2E,4E)-5-((3r,5r,7r)-adamantan-1-yl)-2-benzylhexa-2,4-dienoate (3s): colorless oil; yield 36.4 mg (50%); Rf = 0.39 (PE/EA = 20:1); 1H NMR (400 MHz, CDCl3) δ 7.71 (d, J = 11.7 Hz, 1H), 7.14−7.24 (m, 5H), 6.32 (dd, J = 0.8 Hz, J = 11.7 Hz, 1H), 4.16 (q, J = 7.1 Hz, 2H), 3.79 (s, 2H), 2.03 (s, 3H), 1.90 (s, 3H), 1.64−1.75 (m, 12H), 1.24 (t, J = 7.1 Hz, 3H); 13C NMR (100 MHz, CDCl3) δ 168.5, 157.5, 140.4, 136.3, 129.1, 128.4, 128.3, 125.9, 117.2, 60.5, 40.6, 39.3, 36.9, 32.5, 25.5, 14.3, 13.2; HRMS (ESI, m/z) calcd for C25H33O2 [M

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ASSOCIATED CONTENT

* Supporting Information S

The Supporting Information is available free of charge on the ACS Publications website at DOI: 10.1021/acs.joc.7b02634. 1 H and 13C spectra for all products (PDF)

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AUTHOR INFORMATION

Corresponding Author

*E-mail: [email protected]. ORCID

Jianbo Wang: 0000-0002-0092-0937 Author Contributions §

B.W. and H.Y. contributed equally to this work.

Notes

The authors declare no competing financial interest.

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ACKNOWLEDGMENTS The project is supported by National Basic Research Program of China (973 Program, No. 2015CB856600) and NSFC (Grant Nos. 21472004 and 21332002). We thank Prof. Zhenhua Zhang (China Agricultural University) for providing azide reagents (supported by the National Key Technologies R&D Program of China, 2015BAK45B01, CAU).

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REFERENCES

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