Issue 9, 2022

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

Abstract

The Suzuki–Miyaura cross-coupling of C(sp3)-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.

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

Supplementary files

Article information

Article type
Edge Article
Submitted
04 noy 2021
Accepted
20 yan 2022
First published
21 yan 2022
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry
Creative Commons BY-NC license

Chem. Sci., 2022,13, 2584-2590

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

H. Huang, Q. Dai, H. Leng, Q. Li, S. Yang, Y. Tao, X. Zhang, T. Qi and J. Li, Chem. Sci., 2022, 13, 2584 DOI: 10.1039/D1SC06102J

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