Highly regioselective intermolecular arylation of 1,2,3,4-tetrahydropyridines.
Using a catalytic amount of PdCl2(dppf) x CH2Cl2 in combination with Ag3PO4 and NaOAc, a range of arylated 1,2,3,4-tetrahydropyridines are synthesized in good yields and with complete selectivity at the beta-position. The reaction is compatible with a variety of electron-donating and electron-withdrawing aryl iodides as well as with heteroaryl iodides. The application of these tetrahydropyridines toward the synthesis of polysubstituted piperidines is also demonstrated.
Pelletier
Guillaume
G
Département de Chimie, Université de Montréal, P.O. Box 6128, Station Downtown, Montréal, Québec, Canada H3C 3J7.
Larivée
Alexandre
A
Charette
André B
AB
D002384:Catalysis; D004095:Dihydropyridines / Q000138:chemical synthesis* / Q000737:chemistry; D007454:Iodides / Q000737:chemistry; D015394:Molecular Structure; D010165:Palladium / Q000737:chemistry; D013237:Stereoisomerism
D004095:Dihydropyridines; D007454:Iodides; D010165:Palladium