Cobalt‐Catalyzed Facial‐Selective Hydroalkylation of Cyclopropenes

Author:

Zhang Zhi‐Lin1,Li Zhen1,Xu Yuan‐Tai1,Yu Lu2,Kuang Jian1,Li Yan1,Wang Jia‐Wang1,Tian Changlin12,Lu Xi3ORCID,Fu Yao1

Affiliation:

1. Department of Hepatobiliary Surgery The First Affiliated Hospital Division of Life Sciences and Medicine Hefei National Research Center for Physical Sciences at the Microscale iChEM CAS Key Laboratory of Urban Pollutant Conversion Anhui Province Key Laboratory of Biomass Clean Energy Center for Bioanalytical Chemistry University of Science and Technology of China Hefei 230026 China

2. High Magnetic Field Laboratory Chinese Academy of Sciences Hefei 230031 China

3. Key Laboratory of Precision and Intelligent Chemistry School of Chemistry and Materials Science University of Science and Technology of China Hefei 230026 China

Abstract

AbstractCyclopropene hydrofunctionalization has been a promising strategy for accessing multi‐substituted cyclopropanes; however, cyclopropene hydroalkylation remains underdeveloped. Herein, we report a low‐valent CoH‐catalyzed facial‐selective cyclopropene hydroalkylation to access multi‐substituted cyclopropanes. This reaction exhibits a broad substrate scope of alkyl halides and cyclopropenes and tolerates many functional groups. Moderate‐to‐good facial‐selectivity is obtained without any directing groups. Mechanism studies provide evidence that alkyl radicals are generated from alkyl halides and irreversible CoH insertion is responsible for the facial‐selectivity. Our preliminary exploration demonstrates that asymmetric cyclopropene hydroalkylation can be realized without conspicuous auxiliary groups.

Funder

National Natural Science Foundation of China

Youth Innovation Promotion Association of the Chinese Academy of Sciences

Hefei Science Center, Chinese Academy of Sciences

Fundamental Research Funds for the Central Universities

Publisher

Wiley

Subject

General Chemistry,Catalysis

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