Silver-Catalyzed [3 + 2] Annulation of 2H-Azirines and CF3-Imidoyl Sulfoxonium Ylides: Access to CF3-Substituted 1H- and 2H-Pyrroles

A novel silver-catalyzed [3 + 2] annulation reaction between 2 H -azirines and CF 3 -imidoyl sulfoxonium ylides has been developed, enabling the synthesis of CF 3 -substituted pyrrole derivatives. In this transformation, the CF 3 -imidoyl sulfoxonium ylides are first employed as a C2 synthon to synthesize CF 3 -1 H - and 2 H -pyrroles. This reaction features a broad substrate scope and generates dimethyl sulfoxide as a byproduct. Moreover, the CF 3 -pyrrole derivatives could be synthesized on a gram scale, and a possible catalytic cycle was proposed.