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Taming Gold(I)–Counterion Interplay in the De‐aromatization of Indoles with Allenamides
Author(s) -
Jia Minqiang,
Cera Gianpiero,
Perrotta Daniele,
Monari Magda,
Bandini Marco
Publication year - 2014
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201403155
Subject(s) - counterion , aromatization , cationic polymerization , regioselectivity , chemistry , intramolecular force , lewis acids and bases , bifunctional , electrophile , brønsted–lowry acid–base theory , medicinal chemistry , photochemistry , combinatorial chemistry , stereochemistry , organic chemistry , catalysis , ion
A careful interplay between the π electrophilicity of a cationic Au I center and the basicity of the corresponding counterion allowed for the chemo‐ and regioselective inter‐ as well as intramolecular de‐aromatization of 2,3‐disubstituted indoles with allenamides. The silver‐free bifunctional Lewis acid/Brønsted base complex [{2,4‐( t Bu) 2 C 6 H 3 O} 3 PAuTFA] assisted the formation of a range of densely functionalized indolenines under mild conditions.