4.5 Article

Rhodium(III)-Catalyzed C-H Vinylation of Arenes: Access to Functionalized Styrenes

Journal

CHINESE JOURNAL OF CHEMISTRY
Volume 36, Issue 12, Pages 1143-1146

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/cjoc.201800354

Keywords

C-H activation; olefination; rhodium; C-C coupling; Heck reaction; elimination

Funding

  1. NSFC [21572201, 21772170]
  2. National Basic Research Program of China [2015CB856600]
  3. Fundamental Research Funds for the Central Universities [2018XZZX001-02]

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An effective method has been developed for Rh(III)-catalyzed direct vinylation of arenes to give functionalized styrenes, using vinyltriethoxysilane as a convenient and inexpensive vinyl source. A wide variety of substrates, including 1-aryl-2-pyrrolidinones, anilines, benzamides and ketones, were compatible with this reaction. Moreover, this method can be applied to the two-step synthesis of functionalized indoles. Mechanistic investigation reveals that the reaction probably proceeds through an oxidative Heck/desilylation pathway.

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