Benzylic substitution of gramines with boronic acids and rhodium or iridium catalysts.
Gramine-MeI salts were useful starting materials for the synthesis of 3-benzyl- and 3-allylindoles by the 1,4-addition of boronic acids to the C=C-C=N linkages generated in situ under Rh(I)-catalysis. On the other hand, under Ir(I) catalysis, the reaction of gramines with indoles was used to produce nonsymmetrical diindolylmethanes. [reaction: see text]
de la Herran
Gabriela
G
Departamento de Química OrgAnica, Facultad de Química, Universidad Complutense, 28040-Madrid, Spain.
Segura
Amaya
A
Csákÿ
Aurelio G
AG
D000470:Alkaloids / Q000138:chemical synthesis*; D000498:Allyl Compounds / Q000138:chemical synthesis*; D001593:Benzyl Compounds / Q000138:chemical synthesis*; D001897:Boronic Acids / Q000737:chemistry*; D002384:Catalysis; D026121:Indole Alkaloids; D007211:Indoles / Q000737:chemistry; D007495:Iridium / Q000737:chemistry*; D008697:Methane / Q000031:analogs & derivatives; D008956:Models, Chemical; D012238:Rhodium / Q000737:chemistry*; D013237:Stereoisomerism
D000470:Alkaloids; D000498:Allyl Compounds; D001593:Benzyl Compounds; D001897:Boronic Acids; D026121:Indole Alkaloids; D007211:Indoles; D007495:Iridium; D012238:Rhodium; C007884:gramine; D008697:Methane