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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.

SUBMITTER: Huang H

PROVIDER: S-EPMC8890133 | biostudies-literature | 2022 Mar

REPOSITORIES: biostudies-literature

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

Huang Hua H Dai Qing-Song QS Leng Hai-Jun HJ Li Qing-Zhu QZ Yang Si-Lin SL Tao Ying-Mao YM Zhang Xiang X Qi Ting T Li Jun-Long JL

Chemical science 20220121 9

The Suzuki-Miyaura cross-coupling of C(sp<sup>3</sup>)-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 r ...[more]

PMID: 35356672

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