4.8 Article

Synthesis of Functionalized Organoboron/Silicon Compounds by Copper-Catalyzed Coupling of Alkylsilyl Peroxides and Diboron/Silylborane Reagents

Journal

ORGANIC LETTERS
Volume 21, Issue 7, Pages 2477-2481

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.9b00874

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Funding

  1. JSPS KAKENHI [JP26220803, JP17H06450]
  2. Japan Society for the Promotion of Science

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The facile synthesis of functionalized organoboron/silicon compounds by copper-catalyzed coupling of alkylsilyl peroxides and diboron/silylborane reagents is reported. The reactions proceed smoothly under mild, neutral conditions in short reaction times to generate organoboron/silicon compounds bearing a ketone moiety, which are useful synthetic intermediates that are otherwise difficult to access. The results of mechanistic investigations suggest the radical-mediated formation of carbon-boron and carbon-silicon bonds via beta-scission of alkoxy radicals.

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