Citation: 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. doi: 10.6023/cjoc202003038 shu

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
d.
Zhejiang Jinhua CONBA Bio-Pharm. Co., Ltd., Jinhua, Zhejiang 321016

Corresponding author: Zhang Yicheng, lbqzhych@163.com Wang Lei, leiwang@chnu.edu.cn

^†

Received Date: 15 March 2020
Revised Date: 18 May 2020
Available Online: 27 May 2020
Fund Project: National Natural Science Foundation of China 21772062Project supported by the National Natural Science Foundation of China (No. 21772062)

Figures(2)

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