86803-68-1Relevant articles and documents
Oxidative nitrene transfer from azides to alkynes via Ti(ii)/Ti(iv) redox catalysis: Formal [2+2+1] synthesis of pyrroles
Pearce, Adam J.,See, Xin Yi,Tonks, Ian A.
supporting information, p. 6891 - 6894 (2018/06/26)
Catalytic oxidative nitrene transfer from azides with the early transition metals is rare, and has not been observed without the support of redox noninnocent spectator ligands. Here, we report the formal [2+2+1] coupling of azides and alkynes via TiII/TiIV redox catalysis from simple Ti halide imido precatalysts. These reactions yield polysubstituted N-alkyl pyrroles, including N-benzyl protected pyrroles and rare examples of very electron rich pentaalkyl pyrroles. Mechanistic analysis reveals that [2+2+1] reactions with bulky azides have different mechanistic features from previously-reported reactions using azobenzene as a nitrene source.
Benzvalene and Dewar Benzene Type Sulfinamides
Fongers, K. S.,Hogeveen, H.,Kingma, R. F.
, p. 4275 - 4280 (2007/10/02)
The reaction of cyclobutadiene aluminum halide ? complexes with N-arylsulfinylamines leads, depending on the substitution pattern of the phenyl ring, to either bicyclic (Dewar benzene type) or tricyclic sulfinamides, the latter being formed via an intramolecular Friedel-Crafts reaction of an intermediate cyclobutenyl cation.A similar reaction of aluminum halide ? complex 1 with N-tert-butylsulfinylamine affords both a bicyclic and a tricyclic (benzvalene type) sulfinamide.
