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 | Zendy

Jaric Milica | Zendy; Haag Benjamin A. | Zendy; Unsinn Andreas | Zendy; Karaghiosoff Konstantin | Zendy; Knochel Paul | Zendy

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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.

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