Hg(OAc)(2).0.1Sc(OTf)(3)-catalyzed cycloisomerization of 2-(4-pentynyl)furan

Hirofumi Yamamoto; Ikuo Sasaki; Hiroshi Imagawa; Mugio Nishizawa

doi:10.1021/ol070335m

Hg(OAc)(2).0.1Sc(OTf)(3)-catalyzed cycloisomerization of 2-(4-pentynyl)furan

Org Lett. 2007 Mar 29;9(7):1399-402. doi: 10.1021/ol070335m. Epub 2007 Feb 28.

Authors

Hirofumi Yamamoto¹, Ikuo Sasaki, Hiroshi Imagawa, Mugio Nishizawa

Affiliation

¹ Faculty of Pharmaceutical Sciences, Tokushima Bunri University, Tokushima, Japan.

PMID: 17326651
DOI: 10.1021/ol070335m

Abstract

[structure: see text]. Although the Hg(OTf)2.3TMU-catalyzed Friedel-Crafts-type reaction of 3-(4-pentynyl)furan afforded the exo cyclization product, the reaction of 2-(4-pentynyl)furan furnished a very low yield. We found a 10:1 mixed reagent of Hg(OAc)2 and Sc(OTf)3 showed remarkable catalytic activity for the latter transformation. The actual reacting species is presumed to be Hg(OAc)(OTf), which is efficiently generated in situ by mixing the two reagents.