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Letter
Copper-Catalyzed Cross-Dehydrogenative C-N bond Formation of Azines with Azoles: Overcoming the Limitation of Oxidizing N-O Activation Strategy Kai Sun, Xin Wang, Lulu Liu, Jingjing Sun, Xin Liu, Zhenduo Li, Zhiguo Zhang, and Guisheng Zhang ACS Catal., Just Accepted Manuscript • DOI: 10.1021/acscatal.5b02411 • Publication Date (Web): 02 Nov 2015 Downloaded from http://pubs.acs.org on November 3, 2015
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ACS Catalysis
Copper-Catalyzed Cross-Dehydrogenative C−N bond Formation of Azines with Azoles: Overcoming the Limitation of Oxidizing N−O Activation Strategy Kai Sun,*,†,‡ Xin Wang,† Lulu Liu,† Jingjing Sun,† Xin Liu,† Zhenduo Li,† Zhiguo Zhang,‡ and Guisheng Zhang*,‡ †
College of Chemistry and Chemical Engineering, Anyang Normal University, Anyang 455000, P. R. China Collaborative Innovation Center of Henan Province for Green Manufacturing of Fine Chemicals, Key Laboratory of Green Chemical Media and Reactions, Ministry of Education, School of Chemistry and Chemical Engineering, Henan Normal University, Xinxiang, Henan 453007, P. R. China ‡
ABSTRACT: Here, we report the copper-catalyzed C2 selective cross-dehydrogenative C−N bond formation of azines with azoles. This straightforward method enables us to address the key limitation of prior N–O activation strategy in C2 amination of azines. The wide substrate scope, high functional group tolerance, and ease of operation of the present method are expected to promote its potential application in synthetic chemistry.
KEYWORDS: copper catalysis, C−N bond formation, quinolines, azoles, C2 functionalization Owing to the prevalence of nitrogen-containing compounds in natural products, functional materials, and pharmaceutical agents, chemists have actively sought to develop selective and efficient methodologies allowing for the facile construction of C–N bonds.1 Transition metal-catalyzed or mediated C–N bond formation is regarded as one of the most reliable approaches for nitrogen atom incorporation.2 As an attractive synthetic route, direct C–H amination methods have emerged as step- and atom-economical alternatives.3 As such, impressive achievements in transition metal-catalyzed amination of azoles have been made by Mori et al., Schreiber et al., and other groups.4 In particular, the direct amination of more challenging arene substrates (lacking directing or activating groups) was realized by Ritter et al. and others.5 Despite these achievements, continuous efforts are required, especially for five-membered heterocycles that are easily oxidized and prone to self-homocoupling6 and electron-deficient pyridine and quinoline derivatives. 5d,7 Quinolines are important structural motifs found in medicinal and materials chemistry.8 As a result, the development of synthetic procedures for the facile derivatization of quinolines has been actively investigated. However, the direct C–H functionalization of quinolines still remains a challenge, probably
Scheme 1. C2 amination/imidation of quinolines.
because of the electron deficiency of quinolines. Accordingly, to overcome the relatively low reactivity of azines, an oxygenbased activation strategy has been applied to the nitrogen atom on the azine ring,9 and subsequently examples of C2 arylation, alkenylation, alkylation, acetoxylation, and sulfonylation were
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demonstrated.10 Concurrently, a few elegant C8 alkenylation, arylation, amidation, iodination, and borylation were realized based on N–O directing group by several groups. 11 2Aminoquinolines exist widely in pharmaceuticals and bioactive antagonists.12 Relative to the classic Chichibabin-type reaction,13 two modified strategies have been developed to synthesize 2-amino-quinolines (Scheme 1), whereby expensive 2-chloro-quinolines and 2-mercaptoquinolines are used as starting materials,14 and an oxygen is added to the nitrogen atom of quinolones to increase their reactivity.7,9 Therefore, Table 1: Optimization of the reaction conditionsa
Entry
Oxidant (1.5 equiv.)
Base (2 equiv.)
Solvent (3 mL)
Yield (%)b
1
TBHP
Na2CO3
CH3NO2
0
2
K2S2O8
Na2CO3
CH3NO2
0
3
PhI(OAc)2
Na2CO3
CH3NO2
0
4
BQ
Na2CO3
CH3NO2
0
5
Ag2CO3
Na2CO3
CH3NO2
0
6
Selectfluor
Na2CO3
CH3NO2
82
7
NFSI
Na2CO3
CH3NO2
0
8
[pyF]BF4
Na2CO3
CH3NO2
34
9
Selectfluor
K2CO3
CH3NO2
89
10
Selectfluor
Cs2CO3
CH3NO2
87
11
Selectfluor
KOAc
CH3NO2
41
12
Selectfluor
K3PO4
CH3NO2
27
13
Selectfluor
K2CO3
DMF
0
14
Selectfluor
K2CO3
DMSO
0
15
Selectfluor
K2CO3
CH3CN
trace
16
Selectfluor
K2CO3
DCE
27
17
Selectfluor
K2CO3
1,4-Dioxane
0
18
Selectfluor
K2CO3
C2H5NO2
83
a
Reaction conditions: 1a (0.5 mmol), 2a (2.0 equiv.), Cu(OAc)2 (10 mol%), oxidant (1.5 equiv.), and additive (2.0 equiv.) in solvent (3.0 mL) at 120 °C. bIsolated yield.
the development of direct, highly efficient, and atomiceconomical methods to synthesize 2-aminoquinolines is highly desired. As part of our ongoing interest in C–N bond formation reactions,15 herein, we present a fundamentally different route for copper-catalyzed cross-dehydrogenative C2 functionalization of quinoline derivatives with azoles. Moreover, with this catalytic system, the desired C−N bond formation of six-membered pyridines and five-membered pyrrole, furan, and thiophene can be achieved in moderate-to-high yields. First, we investigated the model reaction of quinoline 1a with 1H-benzo[d][1,2,3]triazole 2a as the coupling partner to optimize the reaction parameters (Table 1). In our previous
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work on copper-catalyzed imidation of five-membered heterocyclic compounds, we found that the combined use of CuII and TBHP (tert-butylhydroperoxide) could efficiently promote the reaction. However, in the presently employed procedure, TBHP did not promote C2 functionalization (Table 1, entry 1). Other oxidants, such as K2S2O8, PhI(OAc)2, BQ (pbenzoquinone), and Ag2CO3, were also ineffective (Table 1, entries 2–5). In contrast, when Selectfluor (1-chloromethyl-4fluoro-1,4-diazonia-bicyclo[2.2.2]-octane bis(tetrafluoroborate) was used as the oxidant, a high yield of the C2 amination product of quinoline was obtained (Table 1, entry 6).16 Therefore, we considered other F+ oxidants including NFSI (N-Fluoro-benzenesulfonimide) and [pyF]BF4 (1fluoropyridi-nium tetrafluoroborate). However, no further improvements in the yield were obtained (Table 1, entries 7 and 8). Subsequently, a range of bases, such as Na2CO3, K2CO3, Cs2CO3, KOAc, and K3PO4, were examined. Among the bases studied, K2CO3 produced the highest yield of 3a (Table 1, entries 9–12). Notably, the system solvents employed also influenced the reaction efficiency. Conducting the reaction in DMF (N,N-dimethylformamide), DMSO (dimethyl sulfoxide), CH3CN, DCE (dichloroethane), and 1,4-dioxane gave the product 3a in very low yields (Table 1, entries 13– 17). In contrast, conducting the reaction in C2H5NO2 gave a satisfactory yield (Table 1, entry 18). After optimization of the reaction conditions, we established a highly efficient route for the C2 functionalization of quinoline (Table 1, entry 9). Using the established optimized conditions, we subsequently examined the scope of quinoline derivatives using 1Hbenzo[d][1,2,3]-triazole 2a as the coupling partner. The representative products are shown in scheme 2. Quinoline derivatives bearing electron-donating methyl group and electronwithdrawing ester, fluoro, chloro, and bromo groups at C6 position were successfully applied, generating the corresponding aminated products in good-to-high yields (66–94%). In contrast, quinoline derivative, containing a nitro group at C6 position, was unreactive under these conditions (3l). Furthermore, quinolines with substituents at different positions, such as 3-methyl, 3-bromo, 4-methyl, 4-chloro, 5-bromo, 6-methyl, 6-methoxyl, 6-fluoro, 6-chloro, 6-bromo, 6-ester, 7-methyl, and 8-methyl, were all effective substrates and generated the corresponding C2 amination products, regioselectively (3b– 3n). It is worth noting that during this C2 functionalization procedure, the C8-aminated product was not detected, not even in trace quantities. Furthermore, 8-methylquinoline, which is an active substrate adapted for methyl C(sp3)–H functionalization, was regioselectively functionalized at C2 position (3n). Isoquinoline and quinoxaline were also tested under the optimized reaction conditions, and afforded the corresponding products in high yields (3p and 3q). Azoles are the most widely used and studied heterocyclic compounds, which play an important role in medicinal and pesticide chemistry with a wide range of bioactivities.17 The scope of other simple azoles was also briefly surveyed (scheme 2). Benzimidazole 2b, pyrazole 2c, and 4chloroimidazole 2d were all effective heterocyclic sources, and could readily be introduced at the C2 position of quinoline (3r, 3s, and 3t). In addition to azoles, protected sulfonamide saccharin was also effective nitrogen source and gave the coupling product 3u in 92% yield. Isoquinoline, quinoxaline and quinazoline were also tested with saccharin,
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Scheme 2. Investigation of quinolines 1 and azoles 2a,b
Scheme 3. Investigation of 6-membered pyridines and 5membered pyrrole, furan, and thiophenea,b
Br N
N N N 3a, 89%
N
N
N N N 3c, 79%
N N N
3b, 91% Br
Cl
N
N N N 3d, 88%
N
N
N N N 3f, 77%
N N N
3e, 82% Cl
F N
N
N N N 3g, 94%
N
N N N
3h, 89%
N N N
3i, 93%
O O2N
Br
O N
N
N N N
3j, 85%
N
N N N
3k, 66%
N N N
3l, 0%
a
Cl
N
N N N
3m, 93%
Cl
N
N N N 3n, 94%
N
N N N 3o, 80%
N N
N N
N
N 3p, 78%
N
N
N N
3r, 81%
N
N
3t, 74%
N
O
N
O O S
O 3u, 92%
N N
N
Cl N
O O S N
N N
3q, 73%
3s, 71%
3v, 83%
N
N N N
O O S
O 3w, 81%
N N
N
O O S
O 3x, 64%
a
Reaction conditions: 1 (0.5 mmol), 2 (2.0 equiv.), Cu(OAc)2 (10 mol%), Selectfluor (1.5 equiv.), and K2CO3 (2.0 equiv.) in CH3NO2 (3.0 mL) at 120 °C. bThe percentage yields represents the isolated yields. corresponding products 3v-3x could be obtained in 64%-83% yields. In consideration of the wide scope of quinolines and nitrogen sources, we anticipated that our successful results in this regard would greatly widen the derivatization of quinolines, thereby further expanding the application of quinolines in medicinal and materials chemistry as well as in total synthesis. After successful exploration of the regioselective C2 functionalization of quinolines, we examined six-membered pyridines. As observed in scheme 3, reactions involving 2-, 3,- and 4-Cl pyridines were sluggish under the optimal reaction
Reaction conditions: 4 (0.5 mmol), 2a (2.0 equiv.), Cu(OAc)2 (10 mol%), Selectfluor (1.5 equiv.), and K2CO3 (2.0 equiv.) in CH3NO2 (3.0 mL) at 120 °C. bThe percentage yields represent isolated yields. cC6-Aminated product 5c′ was isolated in 15% yield, and the 1H NMR characterization analysis is presented in the Supporting Information file (ESI). conditions employed, and trace quantities of the aminated products could not even be detected. The yields of pyridines bearing electron-donating methyl and methoxy groups were relatively moderate (43–67%). Interestingly, a mixture of C6and C2-aminated products in a 1:3 ratio of 3-methyl pyridine were observed (5c and 5c′). Additionally, five-membered pyrrole, furan, and thiophene were examined, and respectivelyfurnished 5f, 5g, 5h, and 5i in high yields (81–90%). The present C−N bond formation procedure afforded suppression of the homocoupling of pyrrole, furan, and thiophene. To gain insights in the reaction mechanism, radical scavenger TEMPO (2,2,6,6-tetramethylpiperidine Noxide, 2.0 equiv.) was added to the mixture under the optimal reaction conditions. No obvious decrease in the yield was observed [Eq. (1)]. Concurrent competition reactions between quinoline 1a and its deuterated analog 1a-d1 were also performed. Calculated KIE value (kH/kD = 1.38, SD = 0.07) was obtained from 1H NMR analysis of the residual material mixture [Eq. (2)]. A comparable KIE value (kH/kD = 1.37, SD = 0.04) between pyridine 4a and its deuterated analog 4a-d5 was obtained [Eq. (3)]. Using the established optimized conditions, intermolecular competition experiment between quinoline 1a and its deuterated analog 1a-d7 was carried out, individually. Calculated KIE value (kH/kD = 1.31, SD = 0.02) was obtained. Additionally, intermolecular competition experiment between pyridine 4a and d5-pyridine 4a-d5 was carried out, individually. Calculated KIE value (kH/kD = 1.44, SD = 0.04) was obtained (see ESI). The results of the control
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optimized conditions
+ HN N N
N 1a
TEMPO (2 equiv)
N
N N N 3a, 69%
2a
N H 1a, 0.1 mmol
N D 1a',0.1 mmol
N
N N N
3a
3h k H/k D = 1.37
(D)H (D)H
H(D) N
N N N
2a, 0.4 mmol D N D 4a', 0.1 mmol .
1a
(eq 3)
5a and 5a' Cu(OAc)2, Selectfluor, K2CO3
N
(eq 2)
H(D) optimized conditions
+ HN N N D
D
3h k H/k D = 1.38
CH3NO2, 12 h, 120 oC no 2a was added
(eq 4) N
in University (IRT1061), China Postdoctoral Science Foundation (2015M572110), and Science and Technology Plan Projects of Henan Province (15A150030).
REFERENCES
optimized conditions + HN N N 2a, 0.4 mmol
N H 4a, 0.1 mmol D
(eq 1)
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F
0%, 12 h
experiments, which involved nucleophile 2a as the limiting reagent, ruled out the following mechanism: C2fluorination followed by SNAr [Eq. (4)]. Based on the current findings, we propose a reductive elimination pathway through CuIII complexes, similarly to that suggested in previous studies, although further evidence is required to support such a mechanism.7a,7b In conclusion, we have developed a straightforward and highly efficient protocol for accessing a variety of C2functionalized quinolines and pyridines. This method enables us to address the key limitation of prior built-in oxidizing N–O activation strategy in C2 amination of such azines. The reactions of substrates with functional groups at different positions successfully generated the corresponding products in moderate-to-good yields. Notably, considering the wide application of azines and azoles in pharmaceutical chemistry, this protocol is believed to generate further research interest. Mechanistic studies are underway to understand the nature of this reaction to potentially enable the discovery of new catalytic systems.
ASSOCIATED CONTENT Supporting Information. This material is available free of charge via the Internet at http://pubs.acs.org. Experimental procedures, the kinetic isotope effect experiment, and analytical data for products.
AUTHOR INFORMATION Corresponding Author *E-mail:
[email protected];
[email protected].
Notes Any additional relevant notes should be placed here.
ACKNOWLEDGMENT Financial support was provided by the National Nature Science Foundation of China (Nos. U1504210, 21172056 and 21372065), Program for Changjiang Scholars and Innovative Research Team
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