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Updated: Jul 28, 2025
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Published on: November 9, 2019
Cobalt-Catalyzed Facial-Selective Hydroalkylation of Cyclopropenes
Zhi-Lin Zhang1, Zhen Li1, Yuan-Tai Xu1
1Department 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.
Abstract:
Cyclopropene 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.
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