CO-transfer carbonylation reactions. A catalytic Pauson-Khand-type reaction of enynes with aldehydes as a source of carbon monoxide

Tsumoru Morimoto; Koji Fuji; Ken Tsutsumi; Kiyomi Kakiuchi

doi:10.1021/ja0126881

CO-transfer carbonylation reactions. A catalytic Pauson-Khand-type reaction of enynes with aldehydes as a source of carbon monoxide

J Am Chem Soc. 2002 Apr 17;124(15):3806-7. doi: 10.1021/ja0126881.

Authors

Tsumoru Morimoto¹, Koji Fuji, Ken Tsutsumi, Kiyomi Kakiuchi

Affiliation

¹ Graduate School of Materials Science, Nara Institute of Science and Technology (NAIST), Takayama, Ikoma, Nara 630-0101, Japan. morimoto@ms.aist-nara.ac.jp

PMID: 11942798
DOI: 10.1021/ja0126881

Abstract

The reaction of enynes with aldehydes in the presence of a catalytic amount of [RhCl(cod)](2)/dppp results in the Pauson-Khand-type reaction without the use of gaseous carbon monoxide to give bicyclic cyclopentenones in high yields (14 examples). Aldehydes serve as a source of carbon monoxide, and their carbonyl moiety is transferred to enynes, resulting in the formation of the carbonylated products. This reaction represents the first example of a CO-transfer carbonylation.