Cu-catalyzed enantioconvergent deborylative alkynylation.

ABSTRACT: Alkylboronic pinacol esters represent a highly attractive class of reagents due to their modular synthesis and unique reactivity conferred by the vacant boron p-orbital. However, their direct application in asymmetric C-C cross-coupling reactions remains underexplored. Herein, we report a Cu-catalyzed deborylative strategy to access α-chiral alkynes that delivers good enantioselectivity and accommodates a broad range of functional groups and heterocycles. The reaction is proposed to proceed through a radical-relay pathway: an aminyl radical-mediated C-B bond cleavage followed by Cu-catalyzed asymmetric alkynylation. The reaction mechanism was probed using a combination of radical clock ring-opening study, radical trapping experiments, and enantioconvergence test with enantioenriched starti

SUBMITTER: Head JF 

PROVIDER: S-EPMC12490034 | biostudies-literature | 2025 Nov

REPOSITORIES: biostudies-literature