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Imidazolium Salt‐Catalyzed Friedel–Crafts‐Type Conjugate Addition of Indoles: Analysis of Indole/Imidazolium Complex by High Level ab Initio Calculations
Author(s) -
Narumi Tetsuo,
Tsuzuki Seiji,
Tamamura Hirokazu
Publication year - 2014
Publication title -
asian journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.846
H-Index - 44
eISSN - 2193-5815
pISSN - 2193-5807
DOI - 10.1002/ajoc.201400026
Subject(s) - chemistry , indole test , carbene , friedel–crafts reaction , catalysis , ab initio , salt (chemistry) , lewis acids and bases , computational chemistry , ab initio quantum chemistry methods , solvent , organic chemistry , molecule
Abstract We describe the facile synthesis of 3‐substituted indoles by Friedel–Crafts‐type conjugate addition catalyzed by imidazolium salts. The reactions proceed under mild conditions with no base, solvent, or N‐heterocyclic carbene. Mechanistic studies suggest the potential mechanism operates through the dual activation of indoles involving cation–π interactions of imidazolium cations with indoles and Lewis base activation by chloride anions derived from the imidazolium salts. High‐level ab initio molecular orbital calculations reveal that there is a strong attraction between the imidazolium cation and the indole, and that the electrostatic and induction interactions strongly contributes to the attraction in the indole/imidazolium complex, which is a characteristic feature of the cation–π interaction.

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