First Cross-Coupling Reactions on Tetrazines, Zoltán Novák, András Kotschy, Org. Lett. 2003, 5, 3495-3497. DOI: 10.1021/ol035312w | [Full Text Link] [Supp. Info Link]

A series of substituted chlorotetrazines were reacted with different terminal alkynes under Sonogashira or Negishi coupling conditions to furnish alkynyl-tetrazines in good to moderate yield. The electron-donating properties of the substituent on the tetrazine core were found to have a significant influence on the success of the reaction. These results constitute the first cross-coupling reactions on tetrazines.