Synthesis of carbocyclic aromatic compounds using ruthenium-catalyzed ring-closing enyne metathesis.

Abstract

General synthetic methods of substituted carbocyclic aromatic compounds are reported. Ring-closing enyne metathesis (RCEM)/dehydration of 1,5-octadien-7-yn-4-ols 6 and RCEM/tautomerization of 1,5-octadien-7-yn-4-ones 7 furnished a wide variety of substituted styrenes 4 and 4-vinylphenols 8, respectively. Acyclic precursors 6 and 7 were readily prepared from beta-halo-alpha,beta-unsaturated aldehydes 9 or 3-halo-2-propene-1-ols 13 by utilizing combinations of the Sonogashira coupling, allylation, and the Dess-Martin oxidation. The RCEM/dehydration for the synthesis of 1,3,5-tris(1-phenylethenyl)benzene derivative 4r and the RCEM/RCM/dehydration for the synthesis of 1,1'-binaphthyl derivative 19a are also presented as applications of this method.

• Authors: Hidetoshi Takahashi, Kazuhiro Yoshida, Akira Yanagisawa
• Journal: The Journal of organic chemistry (J Org Chem) Vol. 74 Issue 10 Pg. 3632-40 (May 15 2009) ISSN: 1520-6904 [Electronic] United States
• PMID: 19391588 (Publication Type: Journal Article)