Ti-Catalyzed Multicomponent Oxidative Carboamination of Alkynes with Alkenes and Diazenes

Zachary W. Davis-Gilbert, Letitia J. Yao, Ian A. Tonks

Research output: Contribution to journalArticlepeer-review

36 Scopus citations

Abstract

The inter- or intramolecular oxidative carboamination of alkynes catalyzed by [py2TiCl2NPh]2 is reported. These multicomponent reactions couple alkenes, alkynes and diazenes to form either α,β-unsaturated imines or α-(iminomethyl)cyclopropanes via a TiII/TiIV redox cycle. Each of these products is formed from a common azatitanacyclohexene intermediate that undergoes either β-H elimination or α,γ-coupling, wherein the selectivity is under substrate control.

Original languageEnglish (US)
Pages (from-to)14570-14573
Number of pages4
JournalJournal of the American Chemical Society
Volume138
Issue number44
DOIs
StatePublished - Nov 9 2016

Bibliographical note

Funding Information:
Financial support was provided by the University of Minnesota (start-up funds) and the National Institutes of Health (1R35GM119457). Equipment for the Chemistry Department NMR facility were supported through a grant from the National Institutes of Health (S10OD011952) with matching funds from the University of Minnesota.

Publisher Copyright:
© 2016 American Chemical Society.

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