An extremely facile synthesis of furans, pyrroles, and thiophenes by the dehydrative cyclization of propargyl alcohols.
Furans, pyrroles, and thiophenes are efficiently prepared by gold-catalyzed dehydrative cyclizations of readily available, heteroatom-substituted propargylic alcohols. The reactions are rapid, high-yielding, and procedurally simple, giving essentially pure aromatic heterocycles in minutes under open-flask conditions with catalyst loadings as low as 0.05 mol %.
Aponick
Aaron
A
Department of Chemistry, University of Florida, Gainesville, Florida 32611, USA. aponick@chem.ufl.edu
Li
Chuan-Ying
CY
Malinge
Jeremy
J
Marques
Emerson Finco
EF
D000480:Alkynes / Q000737:chemistry*; D002384:Catalysis; D003500:Cyclization; D005663:Furans / Q000138:chemical synthesis* / Q000737:chemistry*; D020005:Propanols / Q000737:chemistry*; D011758:Pyrroles / Q000138:chemical synthesis* / Q000737:chemistry*; D013876:Thiophenes / Q000138:chemical synthesis* / Q000737:chemistry*
D000480:Alkynes; D005663:Furans; D020005:Propanols; D011758:Pyrroles; D013876:Thiophenes; C028255:propargyl alcohol