Abstract
A set of functionalized alkynylpyridines can be readily obtained using Et<sub>2</sub>O·BF<sub>3</sub> 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 BF<sub>3</sub>-mediated addition reaction followed by a NaBH<sub>4</sub> reduction or acidic workup is also described.
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