Oxidative Cleavage of the C=N Bond on Al(I)

Reaction of the cyclic guanidine TolN?SIMe with the aluminum(I) compound NacNacAl (1) results in the unprecedented cleavage of the C–N multiple bond to give, after rearrangement, the carbene-ligated Al(III) amide, NacNac?Al(NHTol)(SIMe) (6). DFT calculations revealed that these reactions proceed via a bimolecular mechanism in which either the basic Al(I) center or the transient Al?NTol species deprotonates the methyl group of the NacNac ligand. The results were published today in Journal of the American Chemical Society (J. Am. Chem. Soc. 2017, ASAP):
T. Chu, S.F. Vyboishchikov, B.M. Gabidullin, and G.I. Nikonov
“Oxidative Cleavage of the C?N Bond on Al(I)”
J. Am. Chem. Soc. 2017, ASAP [abstract]
DOI: 10.1021/jacs.7b04841