Catalytic alkynylation of ketones and aldehydes using quaternary ammonium hydroxide base

Teruhiko Ishikawa, Tomohiro Mizuta, Kumiko Hagiwara, Toshiaki Aikawa, Takayuki Kudo, Seiki Saito

Research output: Contribution to journalArticle

107 Citations (Scopus)

Abstract

Catalytic alkynylation of diverse ketones and aldehydes using nonmetallic benzyltrimethylammonium hydroxide or a basic resin of the hydroxide type in DMSO is described. Aliphatic or alicyclic carbonyl partners gave satisfactory results, whereas aromatic ones afforded products with low yields. When aromatic aldehydes were reacted with phenylacetylene, enones such as chalcone derivatives were obtained in place of ynols. These organobase-catalyzed systems provide a practical nonmetallic protocol for C-C bond formation.

Original languageEnglish
Pages (from-to)3702-3705
Number of pages4
JournalJournal of Organic Chemistry
Volume68
Issue number9
DOIs
Publication statusPublished - May 2 2003

ASJC Scopus subject areas

  • Organic Chemistry

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