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Regioselective Metalations of Pyrimidines and Pyrazines by Using Frustrated Lewis Pairs of BF 3 ⋅OEt 2 and Hindered Magnesium– and Zinc–Amide Bases
Author(s) -
Groll Klaus,
Manolikakes Sophia M.,
du Jourdin Xavier Mollat,
Jaric Milica,
Bredihhin Aleksei,
Karaghiosoff Konstantin,
Carell Thomas,
Knochel Paul
Publication year - 2013
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.201301694
Subject(s) - regioselectivity , frustrated lewis pair , metalation , chemistry , amide , combinatorial chemistry , pyrazine , lewis acids and bases , stereochemistry , organic chemistry , catalysis
Born of frustration : Using the frustrated Lewis pairs TMP–metal and BF 3 ⋅OEt 2 allows the regioselective metalation of pharmaceutically relevant diazines, such as pyrimidines, purines, and pyrazines. These metalations are often complementary to prior deprotonations performed without BF 3 ⋅OEt 2 . Especially attractive is a new sequential regioselective full functionalization of the pyrazine scaffold with a bulky (TMS) 2 CH substituent.