66725-87-9Relevant articles and documents
BF3-mediated oxidative cross-coupling of pyridines with alkynyllithium reagents and further reductive functionalizations of the pyridine scaffold
León, Thierry,Quinio, Pauline,Chen, Quan,Knochel, Paul
, p. 1374 - 1379 (2014)
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 NaBH 4 reduction or acidic workup is also described. Georg Thieme Verlag Stuttgart New York.