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Contents Vol 68(9)

RhI-Catalyzed Stille-Type Coupling of Diazoesters with Aryl Trimethylstannanes

Zhen Liu A , Ying Xia A C , Sheng Feng A , Shuai Wang A , Di Qiu A , Yan Zhang A and Jianbo Wang A B C
+ Author Affiliations
- Author Affiliations

A 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.

B State Key Laboratory of Organometallic Chemistry, Chinese Academy of Sciences, Shanghai 200032, China.

C Corresponding authors. Email: xiayingbit@163.com; wangjb@pku.edu.cn

Australian Journal of Chemistry 68(9) 1379-1384 https://doi.org/10.1071/CH15218
Submitted: 26 April 2015  Accepted: 28 May 2015   Published: 17 June 2015

Abstract

A RhI-catalyzed cross-coupling of diazoester with arylstannane was developed. This reaction represents the first Stille-type coupling that uses a diazo compound as the coupling partner. The reaction is operationally simple and can be carried out under mild conditions, thus providing an alternative approach for the synthesis of α-aryl esters. RhI–carbene migratory insertion process is suggested to be involved as the key step in this Stille-type coupling.


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