A Silver-Catalyzed Functionalization of 1-Bromoalkynes: Highly Regio-and Stereo-selective Synthesis of (Z)-β-Bromo-1-arylvinyl Aryl Esters

doi:10.6023/cjoc202003038

Chinese Journal of Organic Chemistry ›› 2020, Vol. 40 ›› Issue (8): 2419-2425.DOI: 10.6023/cjoc202003038 Previous Articles Next Articles

银催化1-溴代炔烃的功能化反应:高区域和立体选择性合成(Z)-β-溴-1-芳基乙烯基芳基酯

孙明利^a,b, 张家俊^a,d, 张义成^a,c, 李品华^a,c, 王磊^a,b,c

a 淮北师范大学化学与材料科学学院安徽淮北 235000;
b 台州学院医药化工与材料工程学院浙江台州 318000;
c 中国科学院上海有机化学研究所金属有机国家重点实验室上海 200032;
d 浙江金华康恩贝生物药业有限公司浙江金华 321016

收稿日期:2020-03-15 修回日期:2020-05-18 发布日期:2020-05-29
通讯作者: 张义成, 王磊 E-mail:lbqzhych@163.com;leiwang@chnu.edu.cn
基金资助:
国家自然科学基金（No.21772062）资助项目.

A Silver-Catalyzed Functionalization of 1-Bromoalkynes: Highly Regio-and Stereo-selective Synthesis of (Z)-β-Bromo-1-arylvinyl Aryl Esters

Sun Mingli^a,b, Zhang Jiajun^a,d, Zhang Yicheng^a,c, Li Pinhua^a,c, Wang Lei^a,b,c

a Key Laboratory of Green and Precise Synthetic Chemistry, Ministry of Education, Department of Chemistry, Huaibei Normal University, Huaibei, Anhui 235000;
b Advanced Research Institute and Department of Chemistry, Taizhou University, Taizhou, Zhejiang 318000;
c State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Shanghai 200032;
c Zhejiang Jinhua CONBA Bio-Pharm. Co., Ltd., Jinhua, Zhejiang 321016

Received:2020-03-15 Revised:2020-05-18 Published:2020-05-29
Supported by:
Project supported by the National Natural Science Foundation of China (No. 21772062).

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Abstract

A silver-catalyzed functionalization of 1-bromoalkynes for the highly regio-and stereo-selective synthesis of (Z)-β-bromo-1-arylvinyl aryl esters was developed. In the presence of Ag₂O as a catalyst, and Et₃N as a base, the reactions of 1-bromoalkynes with commercially available aromatic carboxylic acids underwent smoothly to afford the corresponding (Z)-β-bromo-1-arylvinyl aryl esters in good yields. The investigation indicates that Ag₂O plays an important role in the reaction.

Key words: 1-bromoalkynes, (Z)-β-bromo-1-arylvinyl aryl esters, silver catalysis, regio-selectivity, stereo-selectivity

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Sun Mingli, Zhang Jiajun, Zhang Yicheng, Li Pinhua, Wang Lei. A Silver-Catalyzed Functionalization of 1-Bromoalkynes: Highly Regio-and Stereo-selective Synthesis of (Z)-β-Bromo-1-arylvinyl Aryl Esters[J]. Chinese Journal of Organic Chemistry, 2020, 40(8): 2419-2425.

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[1] (a) Corbet, J.-P.; Mignani. G. Chem. Rev. 2006, 106, 2651.
(b) Cahiez, G.; Moyeux, A. Chem. Rev. 2003, 103, 4283.
(c) Amatore, C.; Jutand, A. Acc. Chem. Res. 2000, 33, 314.
(d) Bettinger, H. F.; Filthaus, M. J. Org. Chem. 2007, 72, 9750.
(e) Uchiyama, M.; Furuyama, T. Kobayashi, M.; Matsumoto, Y.; Tanaka, K. J. Am. Chem. Soc. 2006, 128, 8404.
(f) Boukouvalas, J.; Loach, R. P. J. Org. Chem. 2008, 73, 8109.
[2] (a) Goossen, L. J.; Paetzold, J. Angew. Chem., Int. Ed. 2004, 43, 1095.
(b) Zhang, D.; Ready, J. M. Org. Lett. 2005, 7, 5681.
(c) DeBergh, J. R.; Spivey, K. M.; Ready, J. M. J. Am. Chem. Soc. 2008, 130, 7828.
(d) Tang, W.; Liu, D.; Zhang, X. Org. Lett. 2003, 5, 205.
[3] (a) Kowalski, C. J.; Haque, M. S. J. Org. Chem. 1985, 50, 5140.
(b) Kowalski, C. J.; O'Dowd, M. L.; Burke, M. C.; Fields, K. W. J. Am. Chem. Soc. 1980, 102, 5411.
(c) Kowalski, C. J.; Haque, M. S.; Fields, K. W. J. Am. Chem. Soc. 1985, 107, 1429.
[4] Barluenga, J.; Rodríguez, M. A.; Campos, P. J. J. Org. Chem. 1990, 55, 3104.
[5] Chen, Z.; Li, J.; Jiang, H.; Zhu, S.; Li, Y.; Qi, C. Org. Lett. 2010, 12, 3262.
[6] Jiang, G.; Li, J. X.; Zhu, C.; Wu, W.; Jiang, H. Org. Lett. 2017, 19, 4440.
[7] (a) Kowalski, C. J.; Creary, X.; Rollin, A. J.; Burke, M. C. J. Org. Chem. 1978, 43, 2601.
(b) Pincock, J. A.; Yates, K. Can. J. Chem. 1970, 48, 3332.
(c) Chawla, R.; Singh, A. K.; Yadav, L. D. S. Synlett 2013, 1558.
(d) Xia, X.-F.; Gu, Z.; Liu, W.; Wang, N.; Wang, H.; Xia, Y.; Gao, H.; Liu, X. Org. Biomol. Chem. 2014, 12, 9909.
(e) Wang, Y.; Lu, B.; Zhang, L. Chem. Commun. 2010, 46, 9179.
[8] (a) Wu, W.; Jiang, H. Acc. Chem. Res. 2014, 47, 2483.
(b) Trofimov, A.; Chernyak, N.; Gevorgyan, V. J. Am. Chem. Soc. 2008, 130, 13538.
(c) Yoo, W.-J.; Allen, A.; Villeneuve, K.; Tam, W. Org. Lett. 2005, 7, 5853.
(d) Hein, J. E.; Tripp, J. C.; Krasnova, L. B.; Sharpless, K. B.; Fokin, V. V. Angew. Chem., Int. Ed. 2009, 48, 8018.
(e) Crossley, J. A.; Browne, D. L. J. Org. Chem. 2010, 75, 5414.
(f) Xie, L.; Wu, Y.; Yi, W.; Zhu, L.; Xiang, J.; He, W. J. Org. Chem. 2013, 78, 9190.
(g) Wezeman, T.; Zhong, S.; Nieger, M.; Bräse, S. Angew. Chem., Int. Ed. 2016, 55, 3823.
(h) Alcaide, B.; Almendros, P.; Milla, C. L. Adv. Synth. Catal. 2017, 359, 2630.
[9] (a) Rasolofonjatovo, E.; Theeramunkong, S.; Bouriaud, A.; Kolodych, S.; Chaumontet, M.; Taran, F. Org. Lett. 2013, 15, 4698.
(b) Ye, Q.; Cheng, T.; Zhao, Y.; Zhao, J.; Jin R.; Liu, G. ChemCatChem 2015, 7, 1801.
(c) Zhu, G.; Chen, D.; Wang, Y.; Zheng, R. Chem. Commun. 2012, 48, 5796.
(d) Sauermann, N.; Gonzalez, M. J.; Ackermann, L. Org. Lett. 2015, 17, 5316.
(e) Huang, H.-Y.; Cheng, L.; Liu, J.-J.; Wang, D.; Liu, L.; Li, C.-J. J. Org. Chem. 2017, 82, 2656.
(f) Ji, F.; Li, X.; Wu, W.; Jiang, H. J. Org. Chem. 2014, 79, 11246.
(g) Zeng, X.; Liu, S.; Shi, Z.; Xu, B. Org. Lett. 2016, 18, 4770.
(h) Kreuzahler, M.; Daniels, A.; Wölper, C.; Haberhauer, G. J. Am. Chem. Soc. 2019, 141, 1337.
(i) Lyu, X.-L.; Huang, S.-S.; Song, H.-J.; Liu, Y.-X.; Wang, Q.-M. RSC Adv. 2019, 9, 36213.
(j) Pan, R.; Shi, C.; Zhang, D.; Tian, Y.; Guo, S.; Yao, H.; Lin, A. Org. Lett. 2019, 21, 8915.
(k) Zeng, X.; Liu, S.; Hammond, G. B.; Xu, B. ACS Catal. 2018, 8, 904.
[10] (a) Li, Y.; Liu, X.; Ma, D.; Liu, B.; Jiang, H. Adv. Synth. Catal. 2012, 354, 2683.
(b) Zhao, M.; Ming, L.; Tang, J.; Zhao, X. Org. Lett. 2016, 18, 416.
(c) Herrera, A. G.; Nahra, F.; Brill, M.; Nolan, S. P.; Cazin, C. S. J. ChemCatChem. 2016, 8, 3381.
[11] (a) Chen, Z.; Jiang, H.; Li, Y.; Qi, C. Chem. Commun. 2010, 46, 8049.
(b) Kawaguchi, S.-I.; Gonda, Y.; Masuno, H.; Thivũ, H.; Yamaguchi, K.; Shinohara, H.; Sonoda, M.; Ogawa, A. Tetrahedron Lett. 2014, 55, 6779.
[12] Liste, P. J. G.; Francos, J.; Garrido, S. E. G.; Cadierno, V. J. Org. Chem. 2017, 82, 1507.
[13] Li, Y.; Zhao, J.; Chen, H.; Liu, B.; Jiang, H. Chem. Commun. 2012, 48, 3545.
[14] (a) Jiang, G.; Zhu, C.; Li, J.; Wu, W.; Jiang, H. Adv. Synth. Catal. 2017, 359, 1208.
(b) Zeng, X.; Chen, B.; Lu, Z.; Hammond, G. B.; Xu, B. Org. Lett. 2019, 21, 2772.
[15] Wang, S.; Li, P.; Yu, L.; Wang, L. Org. Lett. 2011, 13, 5968.
[16] (a) Chen, L.; Li, H.; Li, P.; Wang, L. Org. Lett. 2016, 18, 3646.
(b) Tan, H.; Li, H.; Ji, W.; Wang, L. Angew. Chem., Int. Ed. 2015, 54, 8374.
(c) Ni, K.; Meng, L.-G.; Wang, K.; Wang, L. Org. Lett. 2018, 20, 2245.
(d) Ni, K.; Meng, L.-G.; Ruan, H.; Wang, L. Chem. Commun. 2019, 55, 8438.
[17] The X-ray single crystal structure of (Z)-2-bromo-1-phenylvinyl 4-nitrobenzoate (3j, CCCD:1990480).

银催化1-溴代炔烃的功能化反应:高区域和立体选择性合成(Z)-β-溴-1-芳基乙烯基芳基酯

A Silver-Catalyzed Functionalization of 1-Bromoalkynes: Highly Regio-and Stereo-selective Synthesis of (Z)-β-Bromo-1-arylvinyl Aryl Esters

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