4.7 Article

Palladium-Catalyzed Hiyama-Type Cross-Coupling Reactions of Arenesulfinates with Organosilanes

Journal

JOURNAL OF ORGANIC CHEMISTRY
Volume 78, Issue 10, Pages 5022-5025

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/jo302791q

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Funding

  1. National Science Foundation of China [21172149]
  2. Science Technology Department of Zhejiang Province [2012R10014-15]

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Palladium-catalyzed Hiyama-type cross-coupling reactions of various arenesulfinates with organosilanes were achieved in good to excellent yields under aerobic conditions at 70 degrees C. Fluoride is essential, and tetrabutylammonium fluoride (TBAF) was shown to be the most efficient additive for these cross-coupling reactions. These cross-coupling reactions of the arenesulfinates provide high yields and show wide functional group tolerance, making them attractive alternative transformations to traditional cross-coupling approaches for carbon-carbon bond construction.

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