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Photocatalytic Borylation of Imines and Alkenes via Decarboxylation of Trimethylamine Carboxyborane: A New Approach for Generating Boryl Radicals

Haowen Jiang, Hao-Ni Qin, Ai-Lian Wang, Rui Zhang, Peng‐Fei Xu

2024Organic Letters15 citationsDOI

Abstract

In this study, we investigated the photocatalytic decarboxylation of trimethylamine carboxyborane under mild conditions, successfully generating boryl radicals for subsequent borylation reactions with imines and various alkenes. This method exhibited broad substrate compatibility, including the functionalization of biologically relevant molecules. Our findings expand the utility of trimethylamine carboxyborane beyond its role as a carbon-monoxide- and drug-releasing agent, highlighting its potential in radical chemistry through decarboxylation. This work establishes a robust foundation for further exploration of the synthetic application of trimethylamine carboxyborane.

Topics & Concepts

ChemistryBorylationDecarboxylationRadicalPhotocatalysisPhotochemistryTrimethylamineOrganic chemistryCombinatorial chemistryArylCatalysisAlkylRadical Photochemical ReactionsOrganoboron and organosilicon chemistryAdvanced Chemical Sensor Technologies