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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 an...

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Detalles Bibliográficos
Autores principales: Aelterman, Maude, Biremond, Tony, Jubault, Philippe, Poisson, Thomas
Formato: Online Artículo Texto
Lenguaje:English
Publicado: John Wiley and Sons Inc. 2022
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9828158/
https://www.ncbi.nlm.nih.gov/pubmed/36067044
http://dx.doi.org/10.1002/chem.202202194
Descripción
Sumario: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.