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 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.

Automated summary

In this study, an NHC/photoredox dual catalytic cross-coupling of alkyl trifluoroborates with acid fluorides was developed. This method offers a novel solution for the classical acylative Suzuki coupling chemistry, allowing for the rapid synthesis of various ketones under mild conditions.