B(C<sub>6</sub>F<sub>5</sub>)<sub>3</sub>-Catalyzed Dehydrogenation of Pyrrolidines to Form Pyrroles
Ana Alvarez-Montoya, Joseph P. Gillions, Laura Winfrey, Rebecca R. Hawker, Kuldip Singh, Fabrizio Ortu, Yukang Fu, Yang Li, Alexander P. Pulis
Abstract
High Resolution Image Download MS PowerPoint Slide Pyrroles are important N -heterocycles found in medicines and materials. The formation of pyrroles from widely accessible pyrrolidines is a potentially attractive strategy but is an underdeveloped approach due to the sensitivity of pyrroles to the oxidative conditions required to achieve such a transformation. Herein, we report a catalytic approach that employs commercially available B(C 6 F 5 ) 3 in an operationally simple procedure that allows pyrrolidines to serve as direct synthons for pyrroles. Mechanistic studies have revealed insights into borane-catalyzed dehydrogenative processes.