Transition‐Metal‐Free BF 3 ‐Mediated Oxidative and Non‐Oxidative Cross‐Coupling of Pyridines | Zendy

Chen Quan | Zendy; León Thierry | Zendy; Knochel Paul | Zendy

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Transition‐Metal‐Free BF 3 ‐Mediated Oxidative and Non‐Oxidative Cross‐Coupling of Pyridines

Author(s) -

Chen Quan,

León Thierry,

Knochel Paul

Publication year - 2014

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.201400750

Subject(s) - reagent , oxidative phosphorylation , chemistry , transition metal , oxidative coupling of methane , combinatorial chemistry , coupling (piping) , oxidative addition , metal , materials science , organic chemistry , catalysis , biochemistry , metallurgy

We report a BF 3 ‐mediated direct alkynylation of pyridines at C(2) by using a variety of alkynyllithium reagents (oxidative cross‐coupling). Moreover, we have developed a novel transition‐metal‐free cross‐coupling method between alkylmagnesium reagents and 4‐substituted pyridines, such as isonicotinonitrile and 4‐chloropyridine, by employing BF 3 ⋅OEt 2 as a promoter. The combination of these methods enabled us to efficiently prepare a range of di‐, tri‐, and tetrasubstituted pyridines.

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