Amination of ethers using chloramine-T hydrate and a copper(i) catalyst
Organic & Biomolecular Chemistry2004Vol. 3(1), pp. 107–107
Citations Over TimeTop 10% of 2004 papers
David P. Albone, Stephen Challenger, Andrew Derrick, Shaun Fillery, Jacob L. Irwin, Christopher M. Parsons, Hiroya Takada, Paul C. Taylor, D. James Wilson
Abstract
Amination of C-H bonds activated by ether oxygen atoms is facile with chloramine-T as nitrene source and copper(I) chloride in acetonitrile as catalyst. For cyclic ethers the hemiaminal products are generally stable and can be isolated pure. For acyclic ethers, the hemiaminal products, as expected, fragment with elimination of alcohol to yield imines. When activation of benzylic positions is remote through a conjugated system, stable benzylamine derivatives are isolated. Mechanistic studies are consistent with concerted insertion of an electrophilic nitrenoid into the C-H bond in the rate-determining step, though in an asynchronous manner with a more activated substrate.
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