Selective synthesis of N-substituted 1,2-dihydropyridines from furans by copper-induced concurrent tandem catalysis.
A novel transformation in which mono- or dialkyl-substituted furans are converted into 1,2-dihydropyridines upon reaction with PhI horizontal lineNTs at room temperature is reported. The reaction is catalyzed by complexes of general formula Tp(x)M (M = Cu, Ag) and consists of a one-pot procedure with four consecutive catalytic cycles. Furan aziridination is followed by aziridine ring-opening, transimination reaction, inverse-electronic-demand aza-Diels-Alder reaction, and a final hydrogen elimination reaction. The mechanism of the overall transformation is proposed where the metal complex displays a crucial role along the reaction pathway.
Laboratorio de Catalisis Homogenea, Departamento de Quimica y Ciencia de los Materiales, Unidad Asociada al CSIC, Campus de El Carmen s/n, Universidad de Huelva, 21007-Huelva, Spain.
Manuel R
MR
Fructos
Eleuterio
E
Alvarez
M Mar
MM
Díaz-Requejo
Pedro J
PJ
Pérez
D002384:Catalysis; D003300:Copper / Q000737:chemistry*; D018360:Crystallography, X-Ray; D004095:Dihydropyridines / Q000138:chemical synthesis* / Q000737:chemistry; D005663:Furans / Q000737:chemistry*; D008958:Models, Molecular; D015394:Molecular Structure; D009942:Organometallic Compounds / Q000737:chemistry*
D004095:Dihydropyridines; D005663:Furans; D009942:Organometallic Compounds; D003300:Copper