Nickel-Catalyzed Reductive Cross-Coupling of Chlorobismuths with Aryl Halides

Chuanqi Liu; Xiaoqian Wang; Zhao Du; Yilei Wang; Zhihua Peng

doi:10.1055/a-2681-5943

Synthesis, Table of Contents

Synthesis
DOI: 10.1055/a-2681-5943

Paper

Published as part of the Special Topic Dedicated to Prof. Paul Knochel

Nickel-Catalyzed Reductive Cross-Coupling of Chlorobismuths with Aryl Halides

Authors

Chuanqi Liu

¹Department of Chemistry, College of Chemistry and Chemical Engineering, China University of Petroleum (East China), Qingdao, Shandong 266580, China (Ringgold ID: RIN71136)
Xiaoqian Wang

¹Department of Chemistry, College of Chemistry and Chemical Engineering, China University of Petroleum (East China), Qingdao, Shandong 266580, China (Ringgold ID: RIN71136)
Zhao Du

¹Department of Chemistry, College of Chemistry and Chemical Engineering, China University of Petroleum (East China), Qingdao, Shandong 266580, China (Ringgold ID: RIN71136)
Yilei Wang

¹Department of Chemistry, College of Chemistry and Chemical Engineering, China University of Petroleum (East China), Qingdao, Shandong 266580, China (Ringgold ID: RIN71136)
Zhihua Peng

¹Department of Chemistry, College of Chemistry and Chemical Engineering, China University of Petroleum (East China), Qingdao, Shandong 266580, China (Ringgold ID: RIN71136)

Abstract

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Dedication

Dedicated to Professor Paul Knochel on the occasion of his 70th birthday.

Abstract

A straightforward and efficient method for the synthesis of valuable arylbismuthanes via nickel-catalyzed cross-electrophilic coupling of chlorobismuths with aryl halides has been reported. This cross-electrophile C(sp²)–Bi coupling reaction is conducted under mild reaction conditions and exhibits a broad substrate scope. Notably, the described protocol tolerates various sensitive functionalities including alcohol, nitrile, ester, ketone, and aldehyde. Moreover, the application of the generated arylbismuthanes to the Pd-catalyzed cross-coupling reaction is demonstrated.

Keywords

Cross-electrophilic coupling - Arylbismuthane - Aryl halide - C(sp²)–Bi coupling - Nickel catalyst

Full Text

References

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Supplementary Material

Supplementary Material (PDF)