Copper-Catalyzed Cascade Multicomponent Reaction of Azides, Alkynes, and Selenium: Synthesis of Ditriazolyl Diselenides

Abstract

A copper-catalyzed cascade multicomponent reaction for synthesizing ditriazolyl diselenides from azides, terminal alkynes, and elemental selenium has been developed. The present reaction features utilizing readily available and stable reagents, high atom-economy, and mild reaction conditions. A possible mechanism is proposed.

Each Interruption is an Opportunity: Novel Synthetic Strategies Explored Through Interrupted Click Reactions

“…The resulting copper (III) complex 128 is unstable and undergoes rapid reductive elimination, leading to the formation of the final product 129 (Scheme 45). [60] On the other hand, benzo [4,5] 2,3]triazoles 130 can be obtained from terminal alkynes and 1,2-bis(2-azidoaryl)diselenides 129 under CuAAC reaction conditions (Scheme 46). [61] In practice, after the formation of the metallacycle 132, it undergoes oxidative intramolecular addition with selenium, forming a complex 133 that rapidly undergoes reductive elimination (Scheme 47).…”

Recent advances in the application of alkynes in multicomponent reactions

“…In 2023, Sun et al 42 synthesized ditriazolyl diselenides (53 and 53′) via the reaction among azides (51 and 51′), terminal alkyne derivatives 50, and elemental selenium 52 in the presence of Cu(CH 3 CN) 4 PF 6 , Me 4 phen, KOH, and tetrabutylammonium bromide in dioxane/H 2 O at 25 °C for 12 h ( Scheme 21 ).…”