Tris(4-bromophenyl)aminium Hexachloroantimonate-Mediated Intermolecular C(sp²)-C(sp³) Free Radical Coupling of Vindoline with β-Ketoesters and Related Compounds.

ABSTRACT: A powerful tris(4-bromophenyl)aminium hexachloroantimonate (BAHA) mediated regioselective intermolecular coupling reaction of vindoline with a wide range of substrates that include β-ketoesters, β-diketones, β-ketoaldehydes, β-ketonitriles, β-ketolactones, β-ketolactams, β-cyanoesters, and malononitriles is detailed. The BAHA-promoted intermolecular sp³/sp² coupling, representing a special class of selective C-H functionalization reactions with direct carbon-carbon bond formation, proceeds with generation of a quaternary center bound to the aryl C15 center of vindoline capable of accommodating of the vinblastine C16' methyl ester and functionalized for subsequent divergent heterocycle introduction. A comprehensive examination of the reaction scope, optimization of sub

SUBMITTER: Zhang J 

PROVIDER: S-EPMC8758398 | biostudies-literature | 2022 Jan

REPOSITORIES: biostudies-literature