Premium
Regioflexibility in the Functionalization of Multiply Halogenated Quinolines
Author(s) -
Marull Marc,
Schlosser Manfred
Publication year - 2004
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.200300610
Subject(s) - chemistry , trifluoromethyl , quinoline , surface modification , bromine , halogenation , trimethylsilyl , organic chemistry , iodine , combinatorial chemistry , fluorine , medicinal chemistry , alkyl
4‐Bromo‐6‐fluoro‐2‐(trifluoromethyl)quinoline ( 1 ) and 4‐bromo‐7‐fluoro‐2‐(trifluoromethyl)quinoline ( 13 ) were selected as model substrates to explore under what conditions regiochemically exhaustive functionalization reactions can be carried out. This goal was achieved by using trimethylsilyl entities and iodine atoms as the sole auxiliary substituents. The organolithium intermediates could be generated and the protective groups removed without impairing the bromine atom present at the 4‐position. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004)