Rapid and scalable photocatalytic C(sp2)–C(sp3) Suzuki−Miyaura cross-coupling of aryl bromides with alkyl boranes

Ting Wan, Luca Capaldo, Jonas Djossou, Angela Staffa, Felix J. Zwart, Bas Bruin and Timothy Noël ()
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Ting Wan: University of Amsterdam
Luca Capaldo: University of Amsterdam
Jonas Djossou: University of Amsterdam
Angela Staffa: University of Amsterdam
Felix J. Zwart: Universiteit van Amsterdam (UvA)
Bas Bruin: Universiteit van Amsterdam (UvA)
Timothy Noël: University of Amsterdam

Nature Communications, 2024, vol. 15, issue 1, 1-11

Abstract: Abstract In recent years, there has been a growing demand for drug design approaches that incorporate a higher number of sp3-hybridized carbons, necessitating the development of innovative cross-coupling strategies to reliably introduce aliphatic fragments. Here, we present a powerful approach for the light-mediated B-alkyl Suzuki−Miyaura cross-coupling between alkyl boranes and aryl bromides. Alkyl boranes were easily generated via hydroboration from readily available alkenes, exhibiting excellent regioselectivity and enabling the selective transfer of a diverse range of primary alkyl fragments onto the arene ring under photocatalytic conditions. This methodology eliminates the need for expensive catalytic systems and sensitive organometallic compounds, operating efficiently at room temperature within just 30 min. We further demonstrate the translation of the present protocol to continuous-flow conditions, enhancing scalability, safety, and overall efficiency of the method. This versatile approach offers significant potential for accelerating drug discovery efforts by enabling the introduction of complex aliphatic fragments in a straightforward and reliable manner.

Date: 2024
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DOI: 10.1038/s41467-024-48212-5

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