Ligand effects in the metal catalysed reactions of N-aryldiazoamides: Ylide formation vs. insertion reactions

Article abstract of DOI:10.1016/S0040-4020(98)00525-0

Diazoamides 1a and 1b were prepared from 2-(O-allyl)- and 2-(S-allyl) anilines 2 respectively. Copper(II) catalysed decomposition of 1 resulted in formation of benzofused heterocycles 7 by [2,3]-rearrangement of the intermediate ylide. Rhodium(II) perfluorbutyramide catalysed reaction, however, gave mainly the indoles 8, 9 whereas rhodium(II) acetate catalysed reaction resulted in a mixture of products, with β-lactams formed by intramolecular C-H insertion predominating. Catalysed decomposition of N- pyridyl diazoamide 13 gave the stable pyridinium ylide 14.