Highly Selective Metalations of Pyridines and Related Heterocycles Using New Frustrated Lewis Pairs or tmp-Zinc and tmp-Magnesium Bases with BF3⋅OEt2

Efficient and selective: Frustrated Lewis pairs based on BF3⋅OEt2 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 i...

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Veröffentlicht in:	Angewandte Chemie International Edition 2010-07, Vol.49 (32), p.5451-5455
Hauptverfasser:	Jaric, Milica, Haag, Benjamin A., Unsinn, Andreas, Karaghiosoff, Konstantin, Knochel, Paul
Format:	Artikel
Sprache:	eng
Schlagworte:	boranes frustrated Lewis pairs metalation N heterocycles regioselectivity
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Beschreibung
Zusammenfassung:	Efficient and selective: Frustrated Lewis pairs based on BF3⋅OEt2 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 BF3⋅OEt2 enable a complete switch of regioselectivity, thus allowing complementary functionalization.
ISSN:	1433-7851 1521-3773
DOI:	10.1002/anie.201002031