Tunable Brønsted Acidity‐Dependent Alkylation and Alkenylation of Indoles | Zendy

Wu Kaikai | Zendy; Wu Ping | Zendy; Wang Liandi | Zendy; Chen Jiping | Zendy; Sun Chenglin | Zendy; Yu Zhengkun | Zendy

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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.

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