Skip to Main content Skip to Navigation
Journal articles

Synthesis of 2-Pyridinemethyl Ester Derivatives from Aldehydes and 2-Alkylheterocycle N-Oxides via Copper-Catalyzed Tandem Oxidative Coupling-Rearrangement

Abstract : Successful benzylic C(sp3)-H acyloxylation of 2-alkylpyridine, 2-alkylpyrazine, and 2-alkylthiazole compounds was achieved using simple aldehydes. This was carried out via a copper-catalyzed tandem reaction, involving oxidative esterification followed by O-atom transfer of the resultant high yield formed Boekelheide intermediate. The method enables the preparation of functional heterocycles and the desymmetrization of 2,6-dialkylpyridines for efficient synthesis of dissymmetric pincer ligands, thus offering a new life for more practical Boekelheide rearrangement.
Document type :
Journal articles
Complete list of metadatas

https://hal-univ-rennes1.archives-ouvertes.fr/hal-01680991
Contributor : Laurent Jonchère <>
Submitted on : Thursday, January 11, 2018 - 11:33:49 AM
Last modification on : Friday, July 10, 2020 - 4:24:33 PM

Identifiers

Citation

Chang-Sheng Wang, Thierry Roisnel, Pierre H. Dixneuf, Jean-François Soulé. Synthesis of 2-Pyridinemethyl Ester Derivatives from Aldehydes and 2-Alkylheterocycle N-Oxides via Copper-Catalyzed Tandem Oxidative Coupling-Rearrangement. Organic Letters, American Chemical Society, 2017, 19 (24), pp.6720-6723. ⟨10.1021/acs.orglett.7b03446⟩. ⟨hal-01680991⟩

Share

Metrics