Efficient Synthesis of α-Haloboronic Esters via Cu-Catalyzed Atom Transfer Radical Addition.

ABSTRACT: The synthesis of α-haloboronic esters via atom transfer radical addition (ATRA) is constrained due to its limited range of compatible substrates or the need to manipulate the olefin coupling partners. Herein, we present a novel approach for their synthesis via Cu-catalyzed ATRA to vinyl boronic esters. The catalyst is proposed to mediate a traditionally inefficient halogen atom transfer of the α-boryl radical intermediate, thus significantly expanding the range of participating substrates relative to established methods. The forty-eight examples illustrate that a wide range of radical precursors, including primary, secondary, and tertiary alkyl halides, readily add across both unsubstituted and α-substituted vinyl pinacol boronic esters. Further, a one-pot, two-step protocol is presented f

SUBMITTER: Ho TD 

PROVIDER: S-EPMC10765605 | biostudies-literature | 2023 Dec

REPOSITORIES: biostudies-literature