4.8 Article

Rh(III)-Catalyzed meta-C-H Alkenylation with Alkynes

Journal

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 141, Issue 1, Pages 76-79

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/jacs.8b11038

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Funding

  1. National Natural Science Foundation of China [21671097, 21331002]
  2. National Science Foundation [CHE-1465292]
  3. Fundamental Research Funds for the Central Universities

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Rh(III)-catalyzed meta-C-H functionalization reactions are still rare. Herein, we report the first example of Rh(III)-catalyzed meta-C-H alkenylation with disubstituted alkynes directed by a U-shaped nitrile template. Exclusive regio-selectivity has been achieved using unsymmetrical aryl and alkyl-disubstituted alkynes to afford synthetically valuable trisubstituted olefins. Propargyl alcohols are also compatible, affording complex allylic alcohols. Notably, transition metal-catalyzed metaalkenylation with alkynes has not been successful with Pd catalysts.

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