Sustainable conjugate addition of indoles catalyzed by acidic ionic liquid immobilized on silica

A new protocol for 1,4-conjugate addition of indoles to vinyl ketones has been developed, employing Lewis acidic ionic liquid immobilized on silica, ILIS-SO(2)Cl, as a catalyst, which exhibited an efficient, mild and recyclable nature. The reaction condition is applicable to various vinyl ketones an...

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Published inSynlett no. 4; pp. 608 - 610
Main Authors Hagiwara, Hisahiro, Sekifuji, Masayoshi, Hoshi, Takashi, Suzuki, Toshio, Quanxi, Bao, Qiao, Kun, Yokoyama, Chiaki
Format Journal Article
LanguageEnglish
Published STUTTGART Thieme Medical Publishers 03.03.2008
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
indoles
ALPHA,BETA-UNSATURATED KETONES
Michael additions
supported catalysis
catalysis
ionic liquids
MICHAEL REACTIONS
ELECTRON-DEFICIENT OLEFINS
WATER
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Abstract A new protocol for 1,4-conjugate addition of indoles to vinyl ketones has been developed, employing Lewis acidic ionic liquid immobilized on silica, ILIS-SO(2)Cl, as a catalyst, which exhibited an efficient, mild and recyclable nature. The reaction condition is applicable to various vinyl ketones and indoles. The mild nature of the reaction condition showed that the acetoxy or TBDMS group in indoles was maintained intact. The catalyst was used six times resulting in 86% average yield.
AbstractList A new protocol for 1,4-conjugate addition of indoles to vinyl ketones has been developed, employing Lewis acidic ionic liquid immobilized on silica, ILIS-SO(2)Cl, as a catalyst, which exhibited an efficient, mild and recyclable nature. The reaction condition is applicable to various vinyl ketones and indoles. The mild nature of the reaction condition showed that the acetoxy or TBDMS group in indoles was maintained intact. The catalyst was used six times resulting in 86% average yield.
Author Sekifuji, Masayoshi
Hoshi, Takashi
Suzuki, Toshio
Quanxi, Bao
Yokoyama, Chiaki
Qiao, Kun
Hagiwara, Hisahiro
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  organization: Tohoku Univ, Inst Multidisciplinary Res Adv Mat, Aoba Ku, Sendai, Miyagi 9808577, Japan
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10.1002/ejoc.200600646
10.1021/ol062446b
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Issue 4
Keywords indoles
ALPHA,BETA-UNSATURATED KETONES
Michael additions
supported catalysis
catalysis
ionic liquids
MICHAEL REACTIONS
ELECTRON-DEFICIENT OLEFINS
WATER
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Snippet A new protocol for 1,4-conjugate addition of indoles to vinyl ketones has been developed, employing Lewis acidic ionic liquid immobilized on silica,...
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Physical Sciences
Science & Technology
Title Sustainable conjugate addition of indoles catalyzed by acidic ionic liquid immobilized on silica
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