Controlled Synthesis of α-Mono- and α,α-Di-Halogenated Ketones Through Coupling of Halogenated Diboromethanes with Carboxylic Acid Esters

Abstract

Halogenated gem-diboron reagents, as structurally unique gem-diborylalkanes, are crucial in organic synthesis chemistry. Herein, we report a strategy with controlled synthesis of α-mono- and α,α-di-halogenated ketones through nucleophilic addition reaction of halogenated diboromethanes with carboxylic acid esters. The substrate scope is broad and the nucleophilic addition reaction proceeds from a diverse range of carboxylic acid esters with bromo- or chloro-diborylmethanes. Moreover, an intriguing heterocyclic compound has been serendipitously synthesized as well.