Regioselective Metalations of Pyrimidines and Pyrazines by Using Frustrated Lewis Pairs of BF 3 ⋅OEt 2  and Hindered Magnesium– and Zinc–Amide Bases | Zendy

Groll Klaus | Zendy; Manolikakes Sophia M. | Zendy; du Jourdin Xavier Mollat | Zendy; Jaric Milica | Zendy; Bredihhin Aleksei | Zendy; Karaghiosoff Konstantin | Zendy; Carell Thomas | Zendy; Knochel Paul | Zendy

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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.

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