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Highly Selective Metalations of Pyridines and Related Heterocycles Using New Frustrated Lewis Pairs or tmp‐Zinc and tmp‐Magnesium Bases with BF 3 ⋅OEt 2
Author(s) -
Jaric Milica,
Haag Benjamin A.,
Unsinn Andreas,
Karaghiosoff Konstantin,
Knochel Paul
Publication year - 2010
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201002031
Subject(s) - regioselectivity , metalation , frustrated lewis pair , lewis acids and bases , chemistry , combinatorial chemistry , magnesium , organic chemistry , catalysis
Efficient and selective : Frustrated Lewis pairs based on BF 3 ⋅OEt 2 and LiCl‐complexed tmpMg or tmpZn amides (tmp=2,2,6,6‐tetramethylpiperidyl) allow the efficient and regioselective metalation of various functionalized N heterocycles (see scheme for examples). Moreover, such metalations carried out in the presence or absence of BF 3 ⋅OEt 2 enable a complete switch of regioselectivity, thus allowing complementary functionalization.