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Catalysis with Diboron(4)/Pyridine: Application to the Broad-Scope [3 + 2] Cycloaddition of Cyclopropanes and Alkenes

Zhengwei Ding, Zhi Liu, Zhijun Wang, Tao Yu, Ming Xu, Jingru Wen, Kaiyan Yang, Hailong Zhang, Liang Xu* and Pengfei Li*

*Shihezi University, Shihezi 832003; Xi’an Jiaotong University, Xi’an 710054, China, Email: xuliang4423shzu.edu.cn, lipengfeixjtu.edu.cn

Z. Ding, Z. Liu, Z. Wang, T. Yu, M. Xu, J. Wen, K. Yang, H. Zhang, L. Xu, P. Li, J. Am. Chem. Soc., 2022, 144, 8870-8882.

DOI: 10.1021/jacs.2c03673



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Abstract

The combination of a diboron(4) compound and a pyridine catalyzes a metal-free [3 + 2] cycloaddition of cyclopropyl ketones to alkenes with 1,2-disubstitution and 1,1,2-trisubstitution patterns to provide challenging cyclopentane compounds with various levels of substitution in generally high to excellent yield and diastereoselectivity.


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proposed boronyl radical catalysis



Key Words

cyclopentanes


ID: J48-Y2022