Metal catalyst-free photo-induced alkyl C–O bond borylation
Guobin Ma, Changzhou Chen, Sangita Talukdar, Xinluo Zhao, Chuanhu Lei, Hegui Gong
Abstract
Metal catalyst free, blue visible light-induced C-O bond borylation of unactivated tertiary alkyl methyl oxalates has been developed to furnish tertiary alkyl boronates. From the secondary alcohols activated with imidazolylthionyl, moderate yields of boronates were attained under standard photo-induced conditions. Preliminary mechanistic studies confirmed the involvement of a (DMF)2-B2cat2 adduct that weakly absorbs light at 437 nm so as to initiate a Bcat radical. A radical-chain process is proposed wherein the alkyl radical is engaged.
Topics & Concepts
AlkylBorylationChemistryCatalysisAdductPhotochemistryMetalMedicinal chemistryOrganic chemistryArylRadical Photochemical ReactionsOrganoboron and organosilicon chemistrySulfur-Based Synthesis Techniques