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Harnessing <i>gem</i>-Diboron Radicals: A Ni-Catalyzed Reductive Coupling Platform for Diverse sp<sup>3</sup>-Rich Molecular Architectures

Zhenqi Wang, Yanjie Yang, Xing-Bang Liu, Siyu Wan, Pin Gao, Yuan Huang

2025Organic Letters5 citationsDOI

Abstract

Herein, we report a practical nickel-catalyzed reductive cross-coupling of α-chloro- gem -diboron compounds with carbon electrophiles, providing efficient access to a broad range of gem -diboron structures, including previously underdeveloped α-arylated derivatives. This transformation proceeds via an underdeveloped gem -diboron radical intermediate pathway and features mild conditions, operational simplicity, excellent regioselectivity, and broad functional group tolerance. Notably, this method overcomes the long-standing challenge of Csp 3 –Csp 3 bond formation using simple alkyl halide electrophiles, thereby expanding access to traditionally elusive molecular scaffolds.

Topics & Concepts

ChemistryHalideAlkylCoupling (piping)NanotechnologyCombinatorial chemistryReductive eliminationFunctional groupRange (aeronautics)Carbon fibersMoleculeSimple (philosophy)Coupling reactionGroup (periodic table)Transformation (genetics)CatalysisCatalytic Cross-Coupling ReactionsAsymmetric Hydrogenation and CatalysisCatalytic C–H Functionalization Methods
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