4.8 Article

On the Pd-Catalyzed Vinylation of Aryl Halides with Tris(alkoxy)vinylsilanes in Water

Journal

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 131, Issue 13, Pages 4584-+

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/ja900333x

Keywords

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Funding

  1. Ministerio de Ciencia e Innovacion [CTQ2005-00795/BQU, CTQ2008-02918/BQU]
  2. FPU
  3. Comunidad de Madrid [S-0505/PPQ/0328-03]

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Pd-catalyzed vinylation of aryl halides with tris(alkoxy)vinylsilanes occurs in aqueous NaOH solution through Heck coupling of the aryl, halide with the silyl olefin followed by desilylation at the Pd center or, at high temperatures, hydrolysis of the C-Si bond. Pd-mediated desilylation does not occur via B-Si elimination under these conditions.

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