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; Tiechun Li; Peiqiu Liao

doi:10.1055/s-0032-1317691

Synthesis, Table of Contents

Synthesis 2012; 44(24): 3743-3756
DOI: 10.1055/s-0032-1317691

paper

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*

^aSchool 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

^aSchool 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

^bDepartment of Chemistry, Northeast Normal University, Changchun, Jilin 130024, P. R. of China

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Abstract

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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.

Key words

heterocycles - coupling - indoles - desulfurizations - catalysis

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References

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