Synthesis of functionalized hydroquinones via [Cp*RuCl2]2-catalyzed cocyclization of alkynes, alpha,beta-unsaturated carbonyl compounds, and carbon monoxide

Takahide Fukuyama; Ryo Yamaura; Yuki Higashibeppu; Takahiro Okamura; Ilhyong Ryu; Teruyuki Kondo; Take-aki Mitsudo

doi:10.1021/ol052291s

Synthesis of functionalized hydroquinones via [Cp*RuCl2]2-catalyzed cocyclization of alkynes, alpha,beta-unsaturated carbonyl compounds, and carbon monoxide

Org Lett. 2005 Dec 22;7(26):5781-3. doi: 10.1021/ol052291s.

Authors

Takahide Fukuyama¹, Ryo Yamaura, Yuki Higashibeppu, Takahiro Okamura, Ilhyong Ryu, Teruyuki Kondo, Take-aki Mitsudo

Affiliation

¹ Department of Chemistry, Graduate School of Science, Osaka Prefecture University, Sakai, Osaka 599-8531, Japan.

PMID: 16354065
DOI: 10.1021/ol052291s

Abstract

[reaction: see text] Catalytic [2 + 2 + 1 + 1] cocyclization reaction of an alkyne, an alkene, and two molecules of carbon monoxide, leading to functionalized hydroquinones, was studied. Using [Cp*RuCl2]2 as a catalyst, we found that a variety of electron-deficient alkenes, such as alpha,beta-unsaturated ketones, esters, amides, and nitriles, can be employed as an alkene coupling partner to give the corresponding hydroquinones.