Amidation–Ketonization–Selenation of Terminal Alkynes Using TEMPO and Elemental Selenium
Dian‐Liang Wang, Nan‐Quan Jiang, Zhong‐Jian Cai, Shun‐Jun Ji
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.
Topics & Concepts
ChemistrySeleniumCopperElemental analysisOxygenCombinatorial chemistryOrganic chemistrySulfur-Based Synthesis TechniquesCatalytic C–H Functionalization MethodsOrganoselenium and organotellurium chemistry