Efficient synthesis of 2-mono- and 2,5-disubstituted furans via the CuI-catalyzed cycloisomerization of alkynyl ketones.
A mild, general, and efficient method for the synthesis of 2-monosubstituted and 2,5-disubstituted furans via the CuI-catalyzed cycloisomerization of alkynyl ketones was developed. It was demonstrated that furans containing both acid- and base-labile groups could be easily synthesized using this methodology. A plausible mechanism for this transformation is proposed.
Kel'in
Alexander V
AV
Department of Chemistry, University of Illinois at Chicago, 845 West Taylor Street, Chicago, Illinois 60607-7061, USA.
Gevorgyan
Vladimir
V
D000480:Alkynes / Q000737:chemistry; D002384:Catalysis; D003300:Copper; D003500:Cyclization; D005663:Furans / Q000138:chemical synthesis* / Q000737:chemistry; D007454:Iodides; D007536:Isomerism; D007659:Ketones / Q000737:chemistry
D000480:Alkynes; D005663:Furans; D007454:Iodides; D007659:Ketones; D003300:Copper; C073870:cuprous iodide