N-Substituted tosyloxyamine derivatives as a new source of metal nitrenes

ORGN 527

Kim Huard, kimhuard@yahoo.com and Hélène Lebel, lebelhe@chimie.umontreal.ca. Département de Chimie, Université de Montréal, PO Box 6128, Station Downtown, Montréal, QC H3C 3J7, Canada

Activation and functionalization of carbon-hydrogen bonds is an actual challenge in organic synthesis. Direct formation of an amine is achieved by insertion of a nitrene intermediate into a carbon-hydrogen bond. Recently we have disclosed the use of tosyloxycarbamates as a novel reagent for the formation of metal nitrene species. It is the first method allowing the formation of such species which do not involve the use of iodine (III) reagent. Both the intra- and the intermolecular version of the C-H bond insertion reaction have been reported using tosyloxycarbamates as starting material. In this communication, we wish to present our investigation focused on the use of trichloroethyl tosyloxycarbamate as well as other tosyloxyamine derivatives having various R1 group as a new source of nitrenes for the intermolecular C-H bond insertion reaction.