Synthesis 2014; 46(10): 1374-1379
DOI: 10.1055/s-0033-1341235
practical synthetic procedures
© Georg Thieme Verlag Stuttgart · New York

BF3-Mediated Oxidative Cross-Coupling of Pyridines with Alkynyllithium Reagents and Further Reductive Functionalizations of the Pyridine Scaffold

Thierry León
Ludwigs-Maximilians-Universität München, Department Chemie, Butenandtstraße 5–13, Haus F, 81377 München, Germany   Fax: +49(89)218077680   Email: Paul.Knochel@cup.uni-muenchen.de
,
Pauline Quinio
Ludwigs-Maximilians-Universität München, Department Chemie, Butenandtstraße 5–13, Haus F, 81377 München, Germany   Fax: +49(89)218077680   Email: Paul.Knochel@cup.uni-muenchen.de
,
Quan Chen
Ludwigs-Maximilians-Universität München, Department Chemie, Butenandtstraße 5–13, Haus F, 81377 München, Germany   Fax: +49(89)218077680   Email: Paul.Knochel@cup.uni-muenchen.de
,
Paul Knochel*
Ludwigs-Maximilians-Universität München, Department Chemie, Butenandtstraße 5–13, Haus F, 81377 München, Germany   Fax: +49(89)218077680   Email: Paul.Knochel@cup.uni-muenchen.de
› Author Affiliations
Further Information

Publication History

Received: 31 March 2014

Accepted: 02 April 2014

Publication Date:
24 April 2014 (online)


Abstract

A set of functionalized alkynylpyridines can be readily obtained using Et2O·BF3 as promoter. Alkynyllithium reagents undergo an addition reaction at position C-2 of pyridines that are rearomatized by oxidative treatment with chloranil. These substituted pyridines can be easily converted into more valuable intermediates. Examples of applications are given as well. Finally, the synthesis of piperidines and lactams via first an oxidative BF3-mediated addition reaction followed by a NaBH4 reduction or acidic workup is also described.

Supporting Information

 
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