Carbene Insertion and Furyl Migration Cascade Toward Benzofurans

T Tu Zeng (School of Chemistry and Chemical Engineering Chongqing University 174 Shazheng Street Chongqing 400044 China) S Shiqing Huang (Renmin University of China , , ,) Y Yingjian Gong (School of Chemistry and Chemical Engineering Chongqing University 174 Shazheng Street Chongqing 400044 China) L Li Li K Keyi Guo (School of Chemistry and Chemical Engineering Chongqing University 174 Shazheng Street Chongqing 400044 China) S Shitian Wu (School of Chemistry and Chemical Engineering Chongqing University 174 Shazheng Street Chongqing 400044 China) H Huiyang Zhan (School of Chemistry and Chemical Engineering Chongqing University 174 Shazheng Street Chongqing 400044 China) S Shiyu Xu X Xingcan Zhang (Sichuan Food Fermentation Industry Research & Design Institute Co., Ltd Chengdu Sichuan 610000 China) B Baosheng Li (Chongqing University , , ,)

Abstract

Abstract Divergent access to complex molecular skeletons from the same set of readily available raw materials has been a primary goal of chemical synthesis, owing to their widespread application in drug research. In this study, a copper‐catalyzed insertion reaction of a disubstituted carbene into an unsaturated imine has been developed to form β,γ‐unsaturated carbonyl compounds with an α‐quaternary carbon center, which subsequently undergo an unprecedented forward 1,2‐/backward 1,4‐furyl migration cascade, ultimately affording a highly substituted benzofuran. A formal 1,3‐furan migration is involved in this multistep cascade sequence, broadening the substrate scope under mild reaction conditions.

Article Details

Volume / Issue Vol. 64, Issue 38
Published September 15, 2025
ISSN 1433-7851
Publisher Wiley

Journal Info

Angewandte Chemie International Edition

Wiley

ISSN: 1433-7851 Physical Sciences

Authors (10)

T

Tu Zeng

School of Chemistry and Chemical Engineering Chongqing University 174 Shazheng Street Chongqing 400044 China

S

Shiqing Huang

Renmin University of China , , ,

Y

Yingjian Gong

School of Chemistry and Chemical Engineering Chongqing University 174 Shazheng Street Chongqing 400044 China

L

Li Li

K

Keyi Guo

School of Chemistry and Chemical Engineering Chongqing University 174 Shazheng Street Chongqing 400044 China

S

Shitian Wu

School of Chemistry and Chemical Engineering Chongqing University 174 Shazheng Street Chongqing 400044 China

H

Huiyang Zhan

School of Chemistry and Chemical Engineering Chongqing University 174 Shazheng Street Chongqing 400044 China

S

Shiyu Xu

X

Xingcan Zhang

Sichuan Food Fermentation Industry Research & Design Institute Co., Ltd Chengdu Sichuan 610000 China

B

Baosheng Li

Chongqing University , , ,