Synthesis 2012; 44(24): 3743-3756
DOI: 10.1055/s-0032-1317691
paper
© Georg Thieme Verlag Stuttgart · New York

Iron(III) Chloride Promoted Desulfitative C–C Coupling Reaction of α-Oxo Ketene Dithioacetals and Indoles: Highly Selective Synthesis of β,β-Bisindolyl and β-Indolyl α,β-Unsaturated Carbonyl Compounds

Haifeng Yu*
a   School of Chemistry and Life Science, Anshan Normal University, Anshan, Liaoning 114007, P. R. of China   Fax: +86(412)2960065   Email: yuhf@mail.asnc.edu.cn
,
Tiechun Li
a   School of Chemistry and Life Science, Anshan Normal University, Anshan, Liaoning 114007, P. R. of China   Fax: +86(412)2960065   Email: yuhf@mail.asnc.edu.cn
,
Peiqiu Liao
b   Department of Chemistry, Northeast Normal University, Changchun, Jilin 130024, P. R. of China
› Author Affiliations
Further Information

Publication History

Received: 05 September 2012

Accepted after revision: 05 November 2012

Publication Date:
16 November 2012 (online)


Abstract

The iron(III) chloride promoted desulfitative C–C coupling of α-oxo ketene dithioacetals with indoles was developed for the synthesis of indole derivatives. In the presence of iron(III) chloride, α-oxo ketene dithioacetals reacted efficiently and highly selectively with C2-unsubstituted or C2-substituted indoles to afford excellent yields of β,β-bisindolyl or β-indolyl α,β-unsaturated carbonyl compounds, respectively.

Supporting Information