Electrochemical Synthesis of gem-Difluoro- and γ-Fluoro-Allyl Boronates and Silanes.

The electrochemical synthesis of fluorinated allyl silanes and boronates was disclosed. The addition of electrogenerated boryl or silyl radicals onto many α-trifluoromethyl or α-difluoromethylstyrenes in an undivided cell allowed the formation of a large panel of synthetically useful gem-difluoro and γ-fluoroallyl boronates and silanes (64 examples, from 31 % to 95 % yield). In addition, a scale up of the reactions under continuous flow was showcased using an electrochemical reactor with promising volumetric productivity (688 g.L-1 .h-1 and 496 g.L-1 .h-1 ). Moreover, the synthetic utility of these building blocks was highlighted through versatile transformations. Finally, plausible reaction mechanisms were suggested to explain the formation of the products. © 2022 The Authors. Chemistry - A European Journal published by Wiley-VCH GmbH.

Citation

Maude Aelterman, Tony Biremond, Philippe Jubault, Thomas Poisson. Electrochemical Synthesis of gem-Difluoro- and γ-Fluoro-Allyl Boronates and Silanes. Chemistry (Weinheim an der Bergstrasse, Germany). 2022 Nov 25;28(66):e202202194

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PMID: 36067044

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