Research & Teaching Faculty

Default Header Image

Selective C-H Activation alpha to Primary Amines. Bridging Metallaaziridines for Catalytic, Intramolecular alpha-Alkylation

TitleSelective C-H Activation alpha to Primary Amines. Bridging Metallaaziridines for Catalytic, Intramolecular alpha-Alkylation
Publication TypeJournal Article
Year of Publication2009
AuthorsBexrud, JA, Eisenberger, P, Leitch, DC, Payne, PR, Schafer, LL
JournalJournal of the American Chemical Society
Volume131
Pagination2116-+
Date PublishedFeb
Type of ArticleArticle
ISBN Number0002-7863
KeywordsALKENES, ALKYNES, BOND ACTIVATION, COMPLEXES, GENERATION, HYDROAMINOALKYLATION, INTERMOLECULAR HYDROAMINATION, NITROGEN, REACTIVITY, UNACTIVATED OLEFINS
Abstract

Selective alpha-C-H activation results in the synthesis of the first bridging metallaaziridine complex for the catalytic alpha-alkylation of primary amines. Reaction development led to the preparation of new Zr 2-pyridonate complexes for this useful transformation. No nitrogen protecting groups are required for this reaction, which is capable of assembling quaternary chiral centers a to nitrogen. Preliminary mechanistic investigations suggest bridging metallaaziridine species are the catalytically active intermediates for this alpha-functionalization reaction, while monomeric imido complexes furnish azepane hydroamination products.

URL<Go to ISI>://000264792200038