Base-Mediated Radical Borylation of Alkyl Sulfones.

A practical and direct method was developed for the production of versatile alkyl boronate esters via transition metal-free borylation of primary and secondary alkyl sulfones. The key to the success of the strategy is the use of bis(neopentyl glycolato) diboron (B2 neop2 ), with a stoichiometric amount of base as a promoter. The practicality and industrial potential of this protocol are highlighted by its wide functional group tolerance, the late-stage modification of complex compounds, no need for further transesterification, and operational simplicity. Radical clock, radical trap experiments, and EPR studies were conducted which show that the borylation process involves radical intermediates. © 2021 The Authors. Chemistry - A European Journal published by Wiley-VCH GmbH.

Citation

Mingming Huang, Jiefeng Hu, Ivo Krummenacher, Alexandra Friedrich, Holger Braunschweig, Stephen A Westcott, Udo Radius, Todd B Marder. Base-Mediated Radical Borylation of Alkyl Sulfones. Chemistry (Weinheim an der Bergstrasse, Germany). 2022 Jan 13;28(3):e202103866

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PMID: 34713940

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