Increased Efficiency in Cross-Metathesis Reactions of Sterically Hindered Olefins

Ian C. Stewart, Christopher J. Douglas, and Robert H. Grubbs*
The Arnold and Mabel Beckman Laboratory of Chemical Synthesis, Division of Chemistry and Chemical Engineering, California Institute of Technology, Pasadena, California 91125
Org. Lett., 2008, 10 (3), pp 441–444
DOI: 10.1021/ol702624n
Publication Date (Web): January 5, 2008
Copyright © 2008 American Chemical Society

Abstract

Abstract Image

Efficiency in olefin cross-metathesis reactions is affected upon reducing the steric bulk of N-heterocyclic carbene ligands of ruthenium-based catalysts. For the formation of disubstituted olefins containing one or more allylic substituents, the catalyst bearing N-tolyl groups is more efficient than the corresponding N-mesityl catalyst. In contrast, the formation of trisubstituted olefins is more efficient using the N-mesityl-containing catalyst. A hypothesis to explain this dichotomy is described.

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History

  • Published In Issue February 07, 2008
  • Received October 29, 2007

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