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Rh(II)/Pd(0) Dual Catalysis: Regio-divergent Transformations of Alkylic Oxonium Ylides Zi-Sheng Chen, Xiao-Yan Huang, Ling-Hang Chen, Jin-Ming Gao, and Kegong Ji ACS Catal., Just Accepted Manuscript • DOI: 10.1021/acscatal.7b02909 • Publication Date (Web): 19 Oct 2017 Downloaded from http://pubs.acs.org on October 19, 2017
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ACS Catalysis
Rh(II)/Pd(0) Dual Catalysis: Regio-divergent Transformations of Alkylic Oxonium Ylides Zi-Sheng Chen*, Xiao-Yan Huang, Ling-Hang Chen, Jin-Ming Gao, and Kegong Ji* Shaanxi Key Laboratory of Natural Products & Chemical Biology, College of Chemistry and Pharmacy, Northwest A&F University, Yangling,712100, Shaanxi, P. R. China. ABSTRACT: A Rh(II)/Pd(0) dual catalysis strategy that promotes the regio-divergent transformations of alkylic oxonium ylides from α-diazo-β-ketoesters has been developed. Poly-functionalized dihydrofuran-3-ones with an O-substituted quaternary carbon center and 2, 3-disubstituted benzofurans can be selectively obtained in good to excellent yields at room temperature by one-pot. The reaction mechanism was further investigated by the control, step-wise, and crossover experiments.
Key word: Cooperative, Dual catalysis, -Allyl palladium complex, Rhodium-carbenoids, Oxonium ylides, Quaternary carbon center
INTRODUCTION Dual catalysis where two different catalysts work concurrently are sought after to achieve the reactivity and selectivity of the reactions that would be difficult or unattainable with current mono-catalysis.1-5 Remarkable progress in this area has been achieved by combining transition-metal catalysts with organocatalysts.1b-f By contrast, the development of dual transitionmetal catalysis is hampered,1a, 2-5 which may be attributed partly to the inherent difficulty of ensuring redox-compatibility between the two transition-metal catalysts.5 Recent milestones in dual transition-metal catalysis have mostly been successful by combining carbophilic lewis acidic Au(I) catalyst with lewis basic Pd(0) catalyst.3-5 Blum et al.3b pioneered a valuable Au(I)/Pd(0) “catalyzed catalysis” strategy. Au(I)-associated oxonium zwitterions A,6 which were generated by Au(I)catalyzed intramolecular oxy-auration of allenoates, undergon net 1,4-allyl migration to afford substituted butenolides by Pd(0) catalyst (left, Figure 1A). Alternatively, Nevado et al. 4 developed an cooperative Au(I)/Pd(0) dual catalyzed crosscoupling of Au(I)-associated oxonium zwitterions A with ArPd(II)-I species from aryl iodides (right, Figure 1A). Herein, we disclose regio-divergent transformations of Rh(II)associated alkylic oxonium ylides B from α-diazo-β-ketoesters 17 via Rh(II)/Pd(0) dual catalysis to accomplish the synthesis of highly functionalized dihydrofuran-3-ones 38 with an Osubstituted quaternary carbon center and 2,3-disubstituted benzofurans 4,9a respectively (Figure 1B). The ylides generated in situ by the transition-metalcatalyzed decomposition of α-diazo carbonyl compounds in the presence of a heteroatom are known to undergo synthetically useful transformations.9-12 In particular, sigmatropic rearrangements of allylic ylides, such as [2,3] and [1,2]rearrangements, represent a powerful set of reactions for the synthesis of complex natural products.9 However, the competition between [2,3] and [1,2]-allylic ylide rearrangements is relatively common.10d,10f Recently, a series of elegant studies by Hu,11 Gong,11a,12 and Schneider7c demonstrated that protic oxonium or ammonium ylides, which were generated in situ
from Rh(II)-catalyzed reactions of α-diazo esters with alcohols or amines, have been utilized in cooperative Rh(II)/phosphoric acid (or Lewis acids) catalyzed nucleophilic
Figure 1. Dual Catalysis: Au(I)/Pd(0) vs Rh(II)/Pd(0) additions instead of the intramolecular proton transfer. 10c As the continuation of our interest in α-diazo carbonyl compounds13a,13c and Rh(II)/Pd(0) dual catalysis,13b-c we envisioned the Rh(II)-catalyzed decomposition of α-diazo-β-ketoesters 1 with a o-alkoxy group would produce Rh(II)-associated alkylic oxonium ylides B.8,9a The cooperative Rh(II)/Pd(0) dual catalysis may enable the allylic alkylation of the Rh(II)-associated alkylic oxonium ylides B with -allyl Pd(II)-intermediates14 generated by Pd(0)-catalyzed oxidative addition of allyl carboxylates 2, in a chemo- and regio-selective manner to achieve the construction of highly functionalized dihydrofuran-3-one scaffolds 3, which are often found in bioactive natural prod-
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ucts, such as griseofulvin (path a, Figure 1B).15 Alternatively, under the assistance of Pd(0) catalyst, the reactivity of Rh(II)associated alkylic oxonium ylides B toward net 1,4-alkyl migration9a,16 would be enhanced, in which the 2,3-disubstituted benzofurans 4 could be obtained (path b, Figure 1B).
RESULTS AND DISCUSSIONS To validate our hypothesis, our investigation began with a redox-compatible Rh(II)/Pd(0) dual catalytic system13b selecting α-diazo-β-ketoester 1a and allyl benzoate 2a as model substrates (Table 1). As expected, when the reaction was carried out at room temperature in the presence of 1.0 mol % Rh2(tBuCO2)4, 2.0 mol % Pd2(dba)3, and 2.2 mol % Xantphos, the desired cross-coupling product 3aa could be isolated in a satisfying 83% yield along with methyl benzoate 5 (entry 1, Table 1). Encouraged by this result, we attempted to optimize the reaction conditions. The reaction efficiency was largely affected by changing the Pd-catalysts or the ligands. For example, when catalytic Pd(PPh3)4 was used, no isolable coupling product was formed (entry 2, Table 1). In contrast, [PdCl(allyl)]2 as the catalyst turned out to be the most choice (entry 6, Table 1). Various other phosphine ligands were tested (entries 7-10, Table 1), but the results were not better than that observed with Xantphos. In addition, when the same reaction was conducted in the presence of Rh2(OAc)4, the reaction efficiency was also not improved (entry 11, Table 1). Other allyl carboxylates such as allyl tert-butyl carbonate did not improve the yield and resulted in 83% yield of 3aa. Table 1. Optimization of the Reaction Conditions. a
(%)c
Xantphos
4
83
-
24
0
Pd(dba)2
Xantphos
4
84
Rh2(tBuCO2)4
Pd(OAc) 2
Xantphos
4
85
5
Rh2(tBuCO2)4
PdCl2
Xantphos
32
69
6
Rh2(tBuCO2)
[Pd(allyl)Cl]
Xantphos
10
89
4
2
7
Rh2(tBuCO2)4
[Pd(allyl)Cl]2
dppp
9
84
8
Rh2(tBuCO2)4
[Pd(allyl)Cl]2
dppf
9
79
9
Rh2(tBuCO2)4
[Pd(allyl)Cl]2
BINAP
9
85
10
Rh2(tBuCO2)4
[Pd(allyl)Cl]2
PPh3
24
0
11
Rh2(OAc)4
[Pd(allyl)Cl]2
Xantphos
24
65
Rh2L4
[Pd]
Ligand
1
Rh2(tBuCO2)4
Pd2(dba)3
2
Rh2(tBuCO2)4
Pd(PPh3)4
3
Rh2(tBuCO2)4
4
aryl ring reacted similarly to the parent compound 1a. However, the yield of dihydrofuran-3-one 3da with 6-position methoxy substituent decreased noticeably, presumably for lower reactivity of rhodium carbenoids. Substrates having fluoro(1f) and bromide substituents (1g and 1h) were also well tolerated providing the corresponding products (3fa-3ha) in excellent yields. Naphthyl substituted α-diazo-β-ketoester 1i also reacted with higher yield (93%) than 1a. When changing the alkoxy group (R1) from methyl to ethyl, or isopropyl, no decrease of the product 3aa yields was observed. However, when the OR1 group was free hydroxy, the desired product 3aa can be observed a little by NMR with all the α-diazo-βketoester consumed and some of allyl benzoate 2a unreacted (eq 1). Controlling the regio-selectivity in the reaction of αdiazo-β-ketoester 1j with two o-methoxy groups is an important issue (eq 2). Gratifyingly, by elevating the reaction temperature to 50 oC, the product 3ja was selectively obtained in good 82% yield, which may be determined by their relative rates of oxonium ylide generation.9a To further demonstrate the versatility of the reaction, various substituted allyl carboxylates 2 were reacted with α-diazoβ-ketoester 1a (bottom part of Scheme 1). Not surprisingly, the 3-phenyl substituted allyl carboxylates bearing an electrondonating methyl (2c) group, and the electron-withdrawing fluro (2d), chloro (2e), trifluoromethyl (2i), and nitro (2j) substituents at the para-position on the phenyl ring were well tolerated affording the corresponding products 3 with good yields of up to 93%. The naphthyl substituted allyl benzoate 2k also reacted effectively to give the desired product 3ak in 87% yield. Interestingly, the reaction with an E/Z-mixture of the sterically demanding ortho-bromide-phenyl substituted allyl benzoate 2f (E/Z = 3:1) afforded only (E)-3af, albeit in decreased yield. Likewise, reaction with an E/Z-mixture of allyl benzoates 2g-2h
3aa
Time (h)b
Entry
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a
Reaction conditions: 1a (0.11M, 1.1 equiv), 2a (0.10 M, 1.0 equiv), Rh2L4 (1.0 mol %), [Pd] (4.0 mol %, based on Pd, and ligand (2.2 mol %) in toluene at room temperature. b Time for disappearance of 2a by TLC. c Isolated yield.
After having optimized the conditions, an array of α-diazoβ-ketoesters 1 were investigated using allyl benzoate 2a as a coupling partner, which given the corresponding functionalized dihydrofuran-3-ones 3 in good to excellent yields (top part of Scheme 1). The α-diazo-β-ketoesters with electron-rich methyl (1b) and methoxy (1c and 1e) substituents on the β-
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ACS Catalysis benzofurans (4b-4d) in good yields. In particular, fluoro (1e) and palladium reactive bromide substituents (1f and 1g) were well tolerated. Furthermore, the naphthyl substituted α-diazoβ-ketoester 1h could also provide the corresponding 2,3disubstituted benzofurans 4h in moderate yield. Exchanging methyl group with an ethyl group (1i) diminished the reaction yield (4i), presumably for ethyl-palladium complex undergoing β-hydride elimination.18
Scheme 1. Synthesis of various functionalized dihydrofuran-3ones 3 with an O-substituted quaternary carbon center. a Reaction conditions: 1 (0.11 M, 1.1 equiv), 2 (0.10 M, 1.0 equiv), [Rh2(tBuCO2)4] (1.0 mol %), [PdCl(allyl)]2 (2.0 mol %), and Xantphos (2.2 mol %) in toluene at room temperature. Time for disappearance of 2 and isolated yields are in parenthesis. b An E/Z mixture of 2f (E/Z = 3:1) was used; c An E/Z mixture of 2g (E/Z = 50:1) was used; d An E/Z mixture of 2h (E/Z = 33:1) was used. e Allyl carbonate 2m was used.
bearing bromide groups at the m- and p-positions also produced the corresponding 3ga and 3ha, respectively, with (E)geometry in good yields. These results clearly imply that the πallyl Pd(II) complex rapidly undergoes η1-η3 isomerization, and the Pd-catalyzed allylic alkylation occurrs at the sterically less demanding terminal carbon.17 The 2-methyl substituted allyl benzoate 2l (R1 = H, R2 = Me) also afforded the corresponding 3al in good yield.Unfortunately, this method could not be extended to include 3-methyl substituted allyl carbonate 2m (R1 = Me, R2 = H).
To our delight, the above optimized Rh(II)/Pd(0) dual catalysis system could also be applied to the net 1,4-alkyl migration of the Rh(II)-associated ylides B (path b, Figure 1B). α-Diazoβ-ketoesters 1 bearing different substituents on the β-aryl ring were investigated. As presented in Scheme 2, it was found that the reaction was not significantly affected by the electronic property of the substituents. Thus, the α-diazo-β-ketoesters having electron-rich methyl (1b) and methoxy (1c and 1d) substituents could produce the corresponding 2,3-disubstituted
Scheme 2 Synthesis of various functionalized 2,3disubstituted benzofurans 4. Reaction conditions: 1 (0.10 M), [Rh2(tBuCO2)4] (1.0 mol %), [PdCl(allyl)]2 (2.0 mol %), and Xantphos (2.2 mol %) in toluene at room temperature. All yields refer to isolated product after chromatography on silica gel.
In order to gain more insight into the mechanism, several experiments were performed. First, the reaction proceeded with lower reactivity (6% yield of 3aa) in the presence of only [PdCl(allyl)]2/Xantphos (eq 3). No coupling reaction occurred using Rh2(tBuCO2)4, which instead provided the 2,3disubstituted benzofuran 4a in 66% yield (eq 4).9a Control experiments showed that both [PdCl(allyl)]2/Xantphos and Rh2(tBuCO2)4 were required to achieve the coupling reaction. Furthermore, we carried out step-wise reactions with α-diazoβ-ketoester 1a and allyl benzoate 2a (eq 5). Although Pirrung et al. reported the intramolecular generation and 1, 4- alkyl shift of oxonium ylide from α-diazo-β-ketoester 1a to provide the 2,3-disubstituted benzofurans 4a by just using the Rh(II) catalyst,9a the reaction efficiency was not better than that observed by Rh(II)/Pd(0) dual-catalytic system (82% yield). Next, when the isolated product 4a was treated with allyl benzoate 2a by employing [PdCl(allyl)]2/Xantphos in toluene, the scarce amount of allylation adduct 3aa was detected by NMR. These results clearly indicated that the Rh(II)/Pd(0) dual catalysis follows the cooperative mechanistic pathway. Finally, a crossover experiment between α-diazo-β-ketoester 1b and 1i was examined (eq 6). As predicted, under the Rh(II)/Pd(0) dual catalytic system, both non-crossover products (4b and 4i) and crossover products (4j and 4a) were obtained by GC-MS analysis of the reaction mixture. Although there was a small difference in the ratio of the products probably due to the different electronic effect of the substituents of 1b and 1i, the crossover products suggested that an intermolecular exchange of the migrating groups was involved in the reaction.3b,5b
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Based on the above experimental results and literature reports, a tentative mechanism for the Rh(II)/Pd(0) dual catalysis reactions is proposed as shown in Scheme 3. The Rh(II)catalyst initially promotes α-diazo-β-ketoesters 1 to give electrophilic Rh(II)-carbenoid A.7,19 The next step could be the formation of Rh(II)-associated (or) methylic oxonium ylide B8,9a by an intramolecular nucleophilic attack of oxygen atom of methoxy group on the carbon atom of Rh(II)-carbenoid A. In cooperative catalysis pathway (Scheme 3a), the Pd(II)associated intermediate D, which was generated from the interaction of -allyl Pd(II)-intermediate C (obtained by Pd(0)catalyzed oxidative addition of allyl carboxylates 2) with Rh(II)-associated (or) methylic oxonium ylide B as a nucleophile,11i may irreversibly undergo allylic alkylation,14 in which the rate of allylic alkylation may be faster than the 1,4methyl shift. Subsequently, the carboxylate demethylates the oxonium to afford dihydrofuran-3-ones 3 with an Osubstituted quaternary carbon center, along with methyl benzoate 5. The latter step is slower than the 1,4-methyl shift. In catalyzed catalysis pathway (Scheme 3b), the demethylation of Rh(II)-associated methylic oxonium ylide B might provide access to the Rh(II)/Pd(II)-associated zwitterionic intermediate E via the oxidative addition of Pd(0) catalyst,3b as demonstrated by crossover experiment summarized in eq 6. Subsequently, the elimination of the Rh(II) catalyst from intermediate E through transmetalation takes place to give the intermediate F, which most likely undergoes C-O bondforming reductive elimination to afford the 2,3-disubstituted benzofurans 4 and regenerates the Pd(0) catalyst.
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Scheme 3. Proposed reaction mechanism
CONCLUSIONS In summary, we have developed the Rh(II)/Pd(0) dual catalyzed cross-couplings that provide a range of polyfunctionalized dihydrofuran-3-one derivatives with an Osubstituted quaternary carbon center and 2,3-disubstituted benzofurans, in good to excellent yields at room temperature by one-pot. More broadly, this reactions offer a new approach for the regio-divergent transformations of alkylic oxonium ylides from α-diazo-β-ketoesters. The control, step-wise, and crossover experiments have gained valuable insight into the mechanism. Especially, the observed crossover provides an evidence for the existence of Rh(II)/Pd(II)-associated zwitterionic intermediate, which may undergo transmetalation and reductive elimination. Further exploration of this strategy of Rh(II)/Pd(0) dual catalysis with diazo compounds is underway in our laboratory. Corresponding Author
[email protected].,
[email protected].
Author Contributions The manuscript was written through contributions of all authors. All authors have given approval to the final version of the manuscript.
Supporting Information. Details of the experimental procedures, characterization data, copies of 1H and 13C NMR
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spectra of products (PDF). This material is available free of charge via the internet at http://pubs.acs.org.
ACKNOWLEDGMENT We thank the National Natural Science Foundation of China (No. 21402154 and 21502150), the Chinese Universities Scientific Fund (No. 2452016093), the Youth Training Project of Northwest A&F University (No. 2452017035 and Z111021404).
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