Benzylic substitution of gramines with boronic acids and rhodium or iridium catalysts

Article abstract of DOI:10.1021/ol063042m

(Chemical Equation Presented) Gramine-Mel 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.