4.8 Article

Single-Electron Transmetalation: Photoredox/Nickel Dual Catalytic Cross-Coupling of Secondary Alkyl β-Trifluoroboratoketones and -esters with Aryl Bromides

Journal

ORGANIC LETTERS
Volume 18, Issue 12, Pages 2994-2997

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.6b01357

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Funding

  1. NIGMS [R01-GM-113878, R01-GM-081376]

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The first cross-coupling of secondary alkyl beta-trifluoroboratoketones and -esters has been achieved through application of photoredox/nickel dual catalysis. Although the related beta-trifluoroboratoamides have been effectively cross-coupled via Pd-catalysis, the corresponding ketones and esters had proven recalcitrant prior to this report. Reactions occur under mild conditions, and a variety of functional groups and sterically and electronically diverse reaction partners are tolerated.

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