Gold superacid-catalyzed preparation of benzo[c]thiophenes

Wouter Debrouwer; Ruben A J Seigneur; Thomas S A Heugebaert; Christian V Stevens

doi:10.1039/c4cc07989b

Gold superacid-catalyzed preparation of benzo[c]thiophenes

Chem Commun (Camb). 2015 Jan 14;51(4):729-32. doi: 10.1039/c4cc07989b. Epub 2014 Nov 24.

Authors

Wouter Debrouwer¹, Ruben A J Seigneur, Thomas S A Heugebaert, Christian V Stevens

Affiliation

¹ SynBioC Research Group, Department of Sustainable Organic Chemistry and Technology, Faculty of Bioscience Engineering, Ghent University, Coupure Links 653, B-9000 Ghent, Belgium. Chris.Stevens@ugent.be.

PMID: 25418863
DOI: 10.1039/c4cc07989b

Abstract

A three-step synthesis of benzo[c]thiophenes is presented in which the key transformation is the gold-catalyzed 5-exo-dig migratory cycloisomerization of a diallyl thioacetal. It was shown that a small amount of in situ generated HAuCl4 from AuCl3 is the active catalytic species. A mechanism was proposed.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Benzene Derivatives / chemical synthesis*
Benzene Derivatives / chemistry
Catalysis
Chlorides / chemistry*
Cyclization
Gold Compounds / chemistry*
Isomerism
Thiophenes / chemical synthesis*
Thiophenes / chemistry

Substances

Benzene Derivatives
Chlorides
Gold Compounds
Thiophenes
gold tetrachloride, acid