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Carbazoles from the [4C+2C] Reaction of 2,3‐Allenols with Indoles
Author(s) -
Guo Binjie,
Huang Xin,
Fu Chunling,
Ma Shengming
Publication year - 2016
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.201604317
Subject(s) - aromatization , regioselectivity , reactivity (psychology) , chemistry , selectivity , combinatorial chemistry , reaction mechanism , catalysis , medicinal chemistry , reaction conditions , organic chemistry , medicine , alternative medicine , pathology
A mild and efficient method using readily available 1‐aryl‐2,3‐allenols and unprotected‐N indoles, Au + ‐catalyzed cyclization, and aromatization to afford the final [4C+2C] products, carbazoles 4, with an excellent selectivity, is reported. The reaction demonstrates excellent regioselectivity and allows the N−H unit to undergo reactivity unprotected. A mechanism involving a spiropolycyclic intermediate has been proposed and synthetic application is also demonstrated.