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Regioselective Synthesis of Indoles via Rhodium‐Catalyzed CH Activation Directed by an In‐Situ Generated Redox‐Neutral Group
Author(s) -
Muralirajan Krishnamoorthy,
Cheng ChienHong
Publication year - 2014
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201400224
Subject(s) - chemistry , regioselectivity , rhodium , oxidizing agent , catalysis , reductive elimination , ketone , functional group , in situ , redox , medicinal chemistry , combinatorial chemistry , atom economy , organic chemistry , polymer
A regioselective synthesis of indoles from arylhydrazine hydrochlorides with alkynes and diethyl ketone catalyzed by a rhodium complex is described. A possible mechanism involving an in‐situ generated oxidizing directing group NNCR 1 R 2 assisted ortho ‐CH activation and reductive elimination are proposed. The catalytic reaction is highly compatible with a wide range of functional arylhydrazines and alkynes. The reaction proceeds under mild reaction conditions and is atom‐step economical.