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Selenophosphoramide-catalyzed diamination and oxyamination of alkenes

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Abstract

A new selenophosphoramide-catalyzed diamination of terminal- and trans-1,2-disubstituted olefins is presented. Key to the success of this transformation was the introduction of a fluoride scavenger, trimethylsilyl trifluoromethanesulfonate (TMSOTf), to prevent a competitive syn-elimination pathway, as was the use of a phosphoramide ligand on selenium to promote the desired substitution reaction. A screen of catalysts revealed that more electron-rich phosphine ligands resulted in higher yields of the desired product, with selenophosphoramides giving the optimal results. A broad range of substrates and functional groups were tolerated and yields were generally good to excellent. For (E)-1,2-disubstituted olefins, diastereoselectivities were always high, giving exclusively anti products. The conditions were also applied to substrates bearing internal nucleophiles such as esters and carbonates, giving rise to 1,2-aminoesters and cyclic carbonates, respectively.

Graphical abstract: Selenophosphoramide-catalyzed diamination and oxyamination of alkenes

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Article information


Submitted
22 Oct 2019
Accepted
22 Dec 2019
First published
26 Dec 2019

This article is Open Access
All publication charges for this article have been paid for by the Royal Society of Chemistry

Chem. Sci., 2020, Advance Article
Article type
Edge Article

Selenophosphoramide-catalyzed diamination and oxyamination of alkenes

J. R. Tabor, D. C. Obenschain and F. E. Michael, Chem. Sci., 2020, Advance Article , DOI: 10.1039/C9SC05335B

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