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Functionalization of Quinolines through Copper‐Catalyzed Regioselective Halogenation Reaction
Author(s) -
Sahoo Harekrishna,
Ramakrishna Isai,
Baidya Mahiuddin
Publication year - 2016
Publication title -
chemistryselect
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.437
H-Index - 34
ISSN - 2365-6549
DOI - 10.1002/slct.201600532
Subject(s) - regioselectivity , halogenation , catalysis , chemistry , halogen , combinatorial chemistry , copper , surface modification , chelation , coupling reaction , organic chemistry , alkyl
A copper‐catalyzed chelation‐controlled remote C–H halogenation of quinolines is developed. The reaction is scalable and proceeded with excellent C5‐regioselectivity offering halogen‐substituted 8‐aminoquinolines in very high yields (up to 97 %). The products were further utilized for various cross‐coupling reactions en route to highly C5‐functinonalized quinolines. As an application, synthesis of a bioactive compound having tumor‐suppressor activity was accomplished.