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Direct Zincation of Functionalized Aromatics and Heterocycles by Using a Magnesium Base in the Presence of ZnCl 2
Author(s) -
Dong Zhibing,
Clososki Giuliano C.,
Wunderlich Stefan H.,
Unsinn Andreas,
Li Jinshan,
Knochel Paul
Publication year - 2009
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.200801558
Subject(s) - metalation , chemistry , reagent , electrophile , pyrazine , aryl , magnesium , zinc , combinatorial chemistry , quinoxaline , base (topology) , organic chemistry , alkyl , catalysis , mathematical analysis , mathematics
A wide range of polyfunctional aryl and heteroaryl zinc reagents were efficiently prepared in THF by using (TMP) 2 Mg ⋅ 2 LiCl (TMP=2,2,6,6‐tetramethylpiperamidyl) in the presence of ZnCl 2 . The possible pathways of this metalation procedure as well as possible reactive intermediates are discussed. This experimental protocol expands the tolerance of functional groups and allows an efficient zincation of sensitive heterocycles such as quinoxaline or pyrazine. The zincated arenes and heteroarenes react with various electrophiles providing the expected products in 60–95 % yield.