Premium
Copper‐Mediated Remote Highly Site‐Selective C–H Bond Bromination and Chlorination of Quinolines at the C5 Position that is Geometrically Difficult to Access
Author(s) -
Rao Naidu Sambasiva,
Reddy Ganapam Manohar,
Sridhar B.,
Sarma Maheswaran Harihara
Publication year - 2017
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201601151
Subject(s) - halogenation , chemistry , nucleophile , substrate (aquarium) , selectivity , reactivity (psychology) , combinatorial chemistry , copper , medicinal chemistry , organic chemistry , catalysis , medicine , oceanography , alternative medicine , pathology , geology
A concise, simple, and efficient method for remote C–H bond halogenation (Br and Cl) of 8‐aminoquinoline scaffolds at the geometrically difficult‐to‐access C5 position was explored with diverse substrate combinations in DMF. This protocol made use of inexpensive CuBr 2 and CuCl 2 as mediators and showed good to excellent yields for as many as 24 substrate combinations. The outstanding site selectivity of the reaction was reflected by the lack of formation of the undesired C7‐halogenated byproduct originating from the high nucleophilic reactivity of the 8‐aminoquinoline scaffold at the C7 position, even if excess amounts of the CuX 2 salts were used.