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Suzuki-type cross-coupling of alkyl trifluoroborates with acid fluoride enabled by NHC/photoredox dual catalysis

The Suzuki–Miyaura cross-coupling of C(sp(3))-hybridised boronic compounds still remains a challenging task, thereby hindering the broad application of alkyl boron substrates in carbon–carbon bond-forming reactions. Herein, we developed an NHC/photoredox dual catalytic cross-coupling of alkyl triflu...

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Detalles Bibliográficos
Autores principales: Huang, Hua, Dai, Qing-Song, Leng, Hai-Jun, Li, Qing-Zhu, Yang, Si-Lin, Tao, Ying-Mao, Zhang, Xiang, Qi, Ting, Li, Jun-Long
Formato: Online Artículo Texto
Lenguaje:English
Publicado: The Royal Society of Chemistry 2022
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8890133/
https://www.ncbi.nlm.nih.gov/pubmed/35356672
http://dx.doi.org/10.1039/d1sc06102j
Descripción
Sumario:The Suzuki–Miyaura cross-coupling of C(sp(3))-hybridised boronic compounds still remains a challenging task, thereby hindering the broad application of alkyl boron substrates in carbon–carbon bond-forming reactions. Herein, we developed an NHC/photoredox dual catalytic cross-coupling of alkyl trifluoroborates with acid fluorides, providing an alternative solution to the classical acylative Suzuki coupling chemistry. With this protocol, various ketones could be rapidly synthesised from readily available materials under mild conditions. Preliminary mechanistic studies shed light on the unique radical reaction mechanism.