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Synfacts 2008(6): 0656-0656  
DOI: 10.1055/s-2008-1072796
Polymer-Supported Synthesis
© Georg Thieme Verlag Stuttgart · New York

Conjugate Addition of Indoles Using ILIS-SO2Cl Catalyst

Contributor(s): Yasuhiro Uozumi, Yutaka Matsuura
H. Hagiwara*, M. Sekifuji, T. Hoshi, T. Suzuki, B. Quanxi, K. Qiao, C. Yokoyama
Niigata University and Tohoku University, Sendai, Japan
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Publikationsverlauf

Publikationsdatum:
21. Mai 2008 (online)

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Significance

The 1,4-conjugate addition of indoles 2 to various vinyl ketones 1 took place in the presence of an ILIS-SO2Cl (20 mol%) to give the corresponding 3-substituted indoles 3 with up to 93% yield (12 examples). This catalyst was separated from the reaction mixture by centrifugation, and reused fives times in the conjugate addition of indole to 3-buten-2-one (79-93% yield). Decrease in catalytic activity was regained by treating the recovered ILIS-SO2Cl with hot thionyl chloride.