Tetrabutylammonium Bromide (TBAB)-Promoted, Pd/Cu-Catalyzed Sonogashira Coupling of N-Tosyl Aryltriazenes.

Abstract

Sonogashira coupling of N-tosyl aryltriazenes is reported to offer arylalkynes in yields up to 92% with the aid of tetrabutylammonium bromide (TBAB) as a dual activator for both the palladium catalyst and aryltriazenes. Common functional groups could be well tolerated, although large electronic effects from alkynes were observed. TBAB-assisted oxidative addition of palladium(0) to aryltriazene instead of in situ formed arylhalide has been proposed to initiate the catalytic cycle.