Direct synthesis of pyrroles from imines, alkynes, and acid chlorides: an isocyanide-mediated reaction.
[reaction: see text] A direct synthesis of pyrroles from imines, acid chlorides, and alkynes mediated by isocyanides is reported. This reaction proceeds with a range of each of these three substrates, providing a method to generate families of pyrroles in high yield. Mechanistic studies suggest this process proceeds via the generation of imino analogues of munchnones, which can undergo in situ coupling with alkynes to liberate isocyanate and form the pyrrole product.
Cyr
Daniel J St
DJ
Department of Chemistry, McGill University, 801 Sherbrooke Street West, Montreal, Quebec H3A 2K6, Canada.
Martin
Nicolas
N
Arndtsen
Bruce A
BA
D000480:Alkynes / Q000737:chemistry*; D002384:Catalysis; D002712:Chlorides / Q000737:chemistry*; D003486:Cyanides / Q000737:chemistry*; D007097:Imines / Q000737:chemistry*; D008956:Models, Chemical; D010165:Palladium / Q000737:chemistry; D011758:Pyrroles / Q000138:chemical synthesis*
D000480:Alkynes; D002712:Chlorides; D003486:Cyanides; D007097:Imines; D011758:Pyrroles; D010165:Palladium