Landman Iris R, Suleymanov Abdusalom A, Fadaei-Tirani Farzaneh, Scopelliti Rosario, Chadwick F Mark, Severin Kay
Institut des Sciences et Ingénierie Chimiques, Ecole Polytechnique Fédérale de Lausanne (EPFL), 1015 Lausanne, Switzerland.
Dalton Trans. 2020 Feb 21;49(7):2317-2322. doi: 10.1039/d0dt00049c. Epub 2020 Feb 4.
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(CF), and PdCl 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.
三氮烯的合成效用基于这样一个事实，即三氮烯官能团可被布朗斯特酸或路易斯酸裂解，释放出重氮化合物。然而，酸的优先配位位点仍是一个有争议的问题。我们通过核磁共振光谱和单晶X射线晶体学分析了三氮烯的三氟甲磺酸、B(CF)和PdCl加合物。在所有情况下，我们都观察到酸与三氮烯的N1原子配位。这一发现不仅与酸诱导的裂解反应相关，而且与三氮烯的金属催化反应相关，三氮烯在有机合成化学中的应用越来越广泛。
