Amidation-Ketonization-Selenation of Terminal Alkynes Using TEMPO and Elemental Selenium

J Org Chem. 2021 Jul 16;86(14):9898-9904. doi: 10.1021/acs.joc.1c01066. Epub 2021 Jun 24.

Abstract

Herein, we present a novel silver- or copper-mediated direct amidation-ketonization-selenation of terminal alkynes for the synthesis of α-oxo-selenoamides. The reaction utilized easily accessible elemental selenium as the source of selenium. In addition, the 18O labeling experiment revealed that TEMPO is the oxygen source of the carbonyl group. The reaction takes advantage of an unsaturated C≡C bond to construct new C═O, C═Se, and C-N bonds in one step.