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Tunable Brønsted Acidity‐Dependent Alkylation and Alkenylation of Indoles
Author(s) -
Wu Kaikai,
Wu Ping,
Wang Liandi,
Chen Jiping,
Sun Chenglin,
Yu Zhengkun
Publication year - 2014
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201400477
Subject(s) - alkylation , chemistry , acrylonitrile , indole test , acetic acid , brønsted–lowry acid–base theory , organic chemistry , catalysis , polymer , copolymer
The Brønsted acid‐mediated alkylation and alkenylation of indoles were efficiently achieved by means of 3‐(dimethylamino)acrylonitrile. Regulating the acidity of the reaction medium with para ‐toluenesulfonic acid monohydrate ( p ‐TsOH⋅H 2 O) and/or acetic acid (HOAc) led to versatile formation of 3‐alkylated and 3‐alkenylated indole derivatives under mild conditions. The 3‐alkylated indole products could be nearly quantitatively transformed to the corresponding separable ( E )‐ and ( Z )‐3‐alkenylated indoles.