Copper-catalyzed cross-coupling of imines, acid chlorides, and organostannanes: a multicomponent synthesis of alpha-substituted amides.
A copper-catalyzed cross-coupling of organotin reagents with imines and acid chlorides is reported. The reaction proceeds efficiently with a range of vinyl-, alkyl-, aryl- and heteroaryl-substituted organostannanes as well as a diverse set of imines of non-enolizable aldehydes. Use of chloroformates also allows for the formation of N-protected alpha-substituted amines. This chemistry has been applied to the synthesis of isoquinoline alkaloid derivatives through the activation of cyclic imines.
Black
Daniel A
DA
Department of Chemistry, McGill University, 801 Sherbrooke Street West, Montreal, Quebec H3A 2K6, Canada.
Arndtsen
Bruce A
BA
D000470:Alkaloids / Q000138:chemical synthesis*; D000577:Amides / Q000138:chemical synthesis*; D002384:Catalysis; D002712:Chlorides / Q000737:chemistry; D003300:Copper / Q000737:chemistry*; D007097:Imines / Q000737:chemistry*; D007202:Indicators and Reagents; D007546:Isoquinolines / Q000138:chemical synthesis*; D009947:Organotin Compounds / Q000737:chemistry*; D013237:Stereoisomerism
D000470:Alkaloids; D000577:Amides; D002712:Chlorides; D007097:Imines; D007202:Indicators and Reagents; D007546:Isoquinolines; D009947:Organotin Compounds; D003300:Copper