Three-component 1,2-carboamination of vinyl boronic esters via amidyl radical induced 1,2-migration

Chem Sci. 2021 Nov 16;12(47):15765-15769. doi: 10.1039/d1sc05811h. eCollection 2021 Dec 8.

ABSTRACT

Three-component 1,2-carboamination of vinyl boronic esters with alkyl/aryl lithium reagents and N-chloro-carbamates/carboxamides is presented. Vinylboron ate complexes generated in situ from the boronic ester and an organo lithium reagent are shown to react with readily available N-chloro-carbamates/carboxamides to give valuable 1,2-aminoboronic esters. These cascades proceed in the absence of any catalyst upon simple visible light irradiation. Amidyl radicals add to the vinylboron ate complexes followed by oxidation and 1,2-alkyl/aryl migration from boron to carbon to give the corresponding carboamination products. These practical cascades show high functional group tolerance and accordingly exhibit broad substrate scope. Gram-scale reaction and diverse follow-up transformations convincingly demonstrate the synthetic potential of this method.

PMID:35003609 | PMC:PMC8654000 | DOI:10.1039/d1sc05811h

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