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

Hidetoshi Takahashi; Kazuhiro Yoshida; Akira Yanagisawa

doi:10.1021/jo900456g

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

J Org Chem. 2009 May 15;74(10):3632-40. doi: 10.1021/jo900456g.

Authors

Hidetoshi Takahashi¹, Kazuhiro Yoshida, Akira Yanagisawa

Affiliation

¹ Department of Chemistry, Graduate School of Science, Chiba University, Yayoi-cho, Inage-ku, Chiba 263-8522, Japan.

PMID: 19391588
DOI: 10.1021/jo900456g

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.