Palladium-catalyzed cyclization/Heck- and cyclization/conjugate-addition-type sequences in the preparation of polysubstituted furans.
Palladium-catalyzed heterocyclization-coupling sequences have been developed starting from buta-1,2,3-trienyl carbinols and electron-deficient alkenes. Polysubstituted furans are formed where the heterocyclic ring originates from the elements of the butatrienyl carbinol while the electron-deficient olefin is incorporated as a C-3 substituent. In most cases, the reaction proceeds via a Heck-type pathway leading to the efficient formation of 3-vinylfurans. However, couplings with methyl vinyl ketone display a divergent behavior to afford selectively either Heck- or hydroarylation-type products depending on reaction conditions.
Aurrecoechea
José M
JM
Departamento de Química Orgánica II, Facultad de Ciencia y Tecnología, Universidad del País Vasco, Apartado 644, 48080 Bilbao, Spain. jm.aurrecoechea@ehu.es
Durana
Aritz
A
Pérez
Elena
E
D000475:Alkenes / Q000737:chemistry; D002074:Butanones / Q000737:chemistry; D002384:Catalysis; D003500:Cyclization; D004583:Electrons; D004852:Epoxy Compounds / Q000737:chemistry; D004952:Esters / Q000737:chemistry; D005663:Furans / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D010100:Oxygen / Q000737:chemistry; D010165:Palladium / Q000737:chemistry*
D000475:Alkenes; D002074:Butanones; D004852:Epoxy Compounds; D004952:Esters; D005663:Furans; D010165:Palladium; C057920:3-buten-2-one; D010100:Oxygen