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Cobalt‐Catalyzed Facial‐Selective Hydroalkylation of Cyclopropenes

Zhilin Zhang, Zhen Li, Yuantai Xu, Lu Yu, Jian Kuang, Yan Li, Jia‐Wang Wang, Changlin Tian, Xi Lu, Yao Fu

2023Angewandte Chemie International Edition43 citationsDOI

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.

Topics & Concepts

CyclopropeneAlkylCatalysisChemistrySelectivityHalideCombinatorial chemistrySubstrate (aquarium)Organic chemistryBiologyEcologyCyclopropane Reaction MechanismsCatalytic C–H Functionalization MethodsCatalytic Alkyne Reactions
Cobalt‐Catalyzed Facial‐Selective Hydroalkylation of Cyclopropenes | Litcius