LIGAND EFFECTS IN THE METAL-CATALYZED REACTIONS OF N-ARYLDIAZOAMIDES - YLIDE FORMATION VS. INSERTION REACTIONS

Authors
MOODY CJ MIAH S SLAWIN AMZ MANSFIELD DJ RICHARDS IC
Citation
Cj. Moody et al., LIGAND EFFECTS IN THE METAL-CATALYZED REACTIONS OF N-ARYLDIAZOAMIDES - YLIDE FORMATION VS. INSERTION REACTIONS, Tetrahedron, 54(33), 1998, pp. 9689-9700
Citations number
40
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron → ACNP
ISSN journal
00404020
Volume
54
Issue
33
Year of publication
1998
Pages
9689 - 9700
Database
ISI
SICI code
0040-4020(1998)54:33<9689:LEITMR>2.0.ZU;2-J
Abstract
Diazoamides 1a and 1b were prepared from 2-(O-allyl)- and 2-(S-allyl) anilines 2 respectively. Copper(II) catalysed decomposition of 1 resul ted in formation of benzofused heterocycles 7 by [2,3]-rearrangement o f the intermediate ylide. Rhodium(II) perfluorbutyramide catalysed rea ction, however, gave mainly the indoles 8, 9 whereas rhodium(II) aceta te catalysed reaction resulted in a mixture of products, with p-lactam s formed by intramolecular C-H insertion predominating. Catalysed deco mposition of N-pyridyl diazoamide 13 gave the stable pyridinium ylide 14, (C) 1998 Elsevier Science Ltd. All rights reserved.