Taming Gold(I)–Counterion Interplay in the De‐aromatization of Indoles with Allenamides | Zendy

Jia Minqiang | Zendy; Cera Gianpiero | Zendy; Perrotta Daniele | Zendy; Monari Magda | Zendy; Bandini Marco | Zendy

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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.

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