Premium
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.
Accelerating Research
Robert Robinson Avenue,
Oxford Science Park, Oxford
OX4 4GP, United Kingdom
Address
John Eccles HouseRobert Robinson Avenue,
Oxford Science Park, Oxford
OX4 4GP, United Kingdom