Gold-catalyzed 1,2-migration of silicon, tin, and germanium en route to C-2 substituted fused pyrrole-containing heterocycles.
An efficient method for the synthesis of fused pyrroloheterocycles from diverse propargyl-substituted heterocycles in the presence of Au-catalyst has been developed. The cascade transformation proceeds via alkyne-vinylidene isomerization with concomitant 1,2-shift of hydrogen, silyl, and stannyl groups. Remarkably, it was also shown that previously unknown 1,2-migration of a germyl group upon alkyne-vinylidene rearrangement occurs under these reaction conditions. This method allows for mild and efficient synthesis of diverse C-2 substituted N-containing heterocycles.
Seregin
Ilya V
IV
Department of Chemistry, University of Illinois at Chicago, Illinois 60607-7061, USA.
Gevorgyan
Vladimir
V
D000480:Alkynes / Q000737:chemistry; D002384:Catalysis; D003500:Cyclization; D005857:Germanium / Q000737:chemistry*; D006046:Gold / Q000737:chemistry*; D006571:Heterocyclic Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D007536:Isomerism; D009942:Organometallic Compounds / Q000737:chemistry; D011758:Pyrroles / Q000138:chemical synthesis* / Q000737:chemistry; D012825:Silicon / Q000737:chemistry*; D014001:Tin / Q000737:chemistry*
D000480:Alkynes; D006571:Heterocyclic Compounds; D009942:Organometallic Compounds; D011758:Pyrroles; D005857:Germanium; D014001:Tin; D006046:Gold; D012825:Silicon