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Regioselective C3 Functionalizations of 9 H ‐Carbazoles via C(sp 2 )−H Insertions of Rh II Carbenoids
Author(s) -
Samala Srinivas,
Shin Jinhwan,
Shim Jae Yul,
Yoo Eun Jeong
Publication year - 2017
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.201700269
Subject(s) - regioselectivity , chemistry , rhodium , amination , sulfonyl , catalysis , stereochemistry , medicinal chemistry , organic chemistry , alkyl
A series of 9 H ‐carbazoles were synthesized via a direct regioselective C3 functionalization through C(sp 2 )−H insertion of α‐imino rhodium(II) carbenoids generated in situ from 1‐sulfonyl‐1,2,3‐triazoles. A variety of 1‐sulfonyl‐1,2,3‐triazoles underwent this reaction in the presence of a rhodium(II) catalyst, and a mechanism was proposed. Further regioselective C−H amination of the obtained 3‐enamido carbazoles to synthesize (indol‐3‐yl)‐9 H ‐carbazoles, biologically valuable motifs, supported the utility of this method.