Brønsted and Lewis acid adducts of triazenes. Issue 7 (4th February 2020)

• Record Type: Journal Article
• Authors: Landman, Iris R.; Suleymanov, Abdusalom A.; Fadaei-Tirani, Farzaneh; Scopelliti, Rosario; Chadwick, F. Mark; Severin, Kay
• Is Part Of: Dalton transactions. Volume 49:Issue 7(2020)
• Page Start: 2317
• Page End: 2322
• Publication Date: 2020-02-04
• Subjects: Chemistry, Inorganic -- Periodicals; Chemistry, Physical and theoretical -- Periodicals; Chemistry, Inorganic -- Periodicals; 546.05
• DOI: 10.1039/d0dt00049c
• Languages: English
• ISSNs: 1477-9226

Abstract

Abstract : Spectroscopy and crystallographic data show that triazenes are protonated at N1 position. Abstract : The synthetic utility of triazenes rests on the fact that the triazene function can be cleaved by Brønsted or Lewis acids, liberating diazonium compounds. However, the preferred coordination site of the acid is still a matter of debate. We have analyzed triflic acid, B(C6 F5 )3, and PdCl2 adducts of triazenes by NMR spectroscopy and single crystal X-ray crystallography. In all cases, we observe coordination of the acid to the N1 atom of the triazene. This finding is not only of relevance for acid-induced cleavage reactions, but also for metal-catalyzed reactions with triazenes, which are increasingly being used in synthetic organic chemistry.