Regiospesific Synthesis of Polysubstituted Phenols via the Palladium-Catalyzed Enyne-Diyne [4 + 2] Cross-Benzannulation Pathway

Vladimir Gevorgyan, Long Guo Quan, Yoshinori Yamamoto

Research output: Contribution to journalArticle

44 Scopus citations

Abstract

An efficient method for the synthesis of polysubstituted phenols via the consecutive palladium-catalyzed enyne-diyne [4 + 2] cross-benzannulation reaction and subsequent deprotection step was developed. In all cases, the reactions proceeded in a regiospecific manner affording the corresponding polysubstituted phenols in good overall yields. It was shown that a more useful one-pot methodology could be applied to the synthesis of polysubstituted phenols 4a-e. The synthetically useful p-methoxyphenylacetylene 13 and its monosilylated derivative 12 were smoothly prepared via exhaustive or partial desilylation of bis-silylated aromatic adduct 8c, respectively.

Original languageEnglish (US)
Pages (from-to)1244-1247
Number of pages4
JournalJournal of Organic Chemistry
Volume63
Issue number4
DOIs
StatePublished - Feb 20 1998
Externally publishedYes

ASJC Scopus subject areas

  • Organic Chemistry

Fingerprint Dive into the research topics of 'Regiospesific Synthesis of Polysubstituted Phenols via the Palladium-Catalyzed Enyne-Diyne [4 + 2] Cross-Benzannulation Pathway'. Together they form a unique fingerprint.

  • Cite this