Dual-catalyst-enabled olefin 1,2-difunctionalization for α-chloroalkylboronic esters

Radical vicinal difunctionalization of olefin represents one of the most efficient ways to combine different fragments. In this issue of Chem, Li, Bunescu, and Gaunt report the modular synthesis of α-chloroalkylboronic esters via additions of aryl group and chlorine atom across the vinyl boronic ester enabled by two different cooperative catalysts. Radical vicinal difunctionalization of olefin represents one of the most efficient ways to combine different fragments. In this issue of Chem, Li, Bunescu, and Gaunt report the modular synthesis of α-chloroalkylboronic esters via additions of aryl group and chlorine atom across the vinyl boronic ester enabled by two different cooperative catalysts. Multicomponent synthesis of α-chloro alkylboronic esters via visible-light-mediated dual catalysisLi et al.ChemNovember 7, 2022In Briefα-Chloro alkylboronic (α-CAB) esters are a class of stable bifunctional molecules wherein the intrinsic differences of a carbon–chlorine and carbon–boron bond can be used to unlock distinct reactivity through carbon-electrophile, carbon-nucleophile, and carbon-centered radical intermediates. Despite their apparent utility, complex variants are not trivial to prepare via established methods. We present a new visible-light-mediated dual catalytic process for the multicomponent coupling of diaryliodonium salts, alkenes, and a simple metal chloride. The broad scope of the reaction combined with the capacity of their synthetic diversification will make this transformation attractive for practitioners of synthetic and medicinal chemistry in academic and industrial environments. Full-Text PDF Open Access