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Well‐Defined, Versatile and Recyclable Half‐Sandwich Nickelacarborane Catalyst for Selective Carbene‐Transfer Reactions

Linghua Wang, Saima Perveen, Yizhao Ouyang, Shuai Zhang, Jiao Jiao, Gang He, Yong Nie, Pengfei Li

2021Chemistry - A European Journal25 citationsDOI

Abstract

Catalytic carbene-transfer reactions constitute a class of highly useful transformations in organic synthesis. Although catalysts based on a range of transition-metals have been reported, the readily accessible nickel(II)-based complexes have been rarely used. Herein, an air-stable nickel(II)-carborane complex is reported as a well-defined, versatile and recyclable catalyst for selective carbene transfer reactions with low catalyst loading under mild conditions. This catalyst is effective for several types of reactions including diastereoselective cyclopropanation, epoxidation, selective X-H insertions (X = C, N, O, S, Si), particularly for the unprotected substrates. This represents a rare example of carborane ligands in base metal catalysis.

Topics & Concepts

CarbeneCyclopropanationCatalysisNickelCarboraneChemistryCombinatorial chemistryTransition metalTransfer hydrogenationPhotochemistryOrganic chemistryRutheniumCyclopropane Reaction MechanismsCatalytic C–H Functionalization MethodsSynthetic Organic Chemistry Methods
Well‐Defined, Versatile and Recyclable Half‐Sandwich Nickelacarborane Catalyst for Selective Carbene‐Transfer Reactions | Litcius