Copper‐Catalyzed Reaction of Aryl Isocyanides with Active Methylene Isocyanides and Arylsulfonothioates: Synthesis of Sulfur‐Containing Trisubstituted Imidazoles

Abstract

A Copper-catalyzed reaction of aryl isocyanides with active methylene isocyanides and arylsulfonothioates is developed for the synthesis of sulfur-containing trisubstituted imidazoles. This reaction not only forms new CÀ C, CÀ N, and CÀ S bonds in one step, but also provides a new strategy for the construction of trisubstituted imidazoles based on the isocyanide-isocyanide [3 + 2] cycloaddition.

Electroreductive Nickel‐Catalyzed Thiolation: Efficient Cross‐Electrophile Coupling for C−S Formation

“…However, they are known to be highly toxic with foul‐smelling odor and this impedes its functionality. In stark contrast, the use of simple, bench‐stable and odorless electrophilic thiosulfonates for the formation of C−S bonds continues to be underdeveloped [5a–c,e,g, 6] . Cross‐electrophile couplings have surfaced as an impressive alternative to conventional cross‐couplings with preformed nucleophiles, providing an advantage in terms of step‐economy [7] .…”

Divergent Reaction of Isocyanides with o-Bromobenzaldehydes: Synthesis of Ketenimines and Lactams with Isoindolinone Cores

“…As versatile organic synthons, isocyanides have been applied to various transformations. − Our group also carried out a series of studies on their C1 uses in transition-metal-catalyzed reactions, radical reactions and ionic reactions . The use of isocyanides as diatomic building blocks was also developed with transition-metal catalysts such as Ag − and Cu, ,, Lewis acids, and metal-free conditions to generate new chemical bonds with both C and N atoms.…”

Recent developments and perspectives in the copper-catalyzed multicomponent synthesis of heterocycles

“…Sulfur-containing trisubstituted imidazoles were successfully prepared via three-component reaction of aryl isocyanides with active methylene isocyanides and arylsulfonothioates in presence of Cu 2 O as catalyst. 17 The trisubstituted imidazoles were constructed based on the isocyanide–isocyanide [3 + 2] cycloaddition and this Cu( i )-catalyzed reaction enabled formation of new C–C, C–S and C–N bonds in single step.…”