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Issue 62, 2017
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o-Phthalaldehyde catalyzed hydrolysis of organophosphinic amides and other P([double bond, length as m-dash]O)–NH containing compounds

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Abstract

Over 50 years ago, Jencks and Gilchrist showed that formaldehyde catalyses the hydrolysis of phosphoramidate through electrophilic activation, induced by covalent attachment to its nitrogen atom. Given our interest in the use of aldehydes as catalysts, this work was revisited to identify a superior catalyst, o-phthalaldehyde, which facilitates hydrolyses of various organophosphorus compounds bearing P([double bond, length as m-dash]O)–NH subunits under mild conditions. Interestingly, chemoselective hydrolysis of the P([double bond, length as m-dash]O)–N bonds could be accomplished in the presence of P([double bond, length as m-dash]O)–OR bonds.

Graphical abstract: o-Phthalaldehyde catalyzed hydrolysis of organophosphinic amides and other P( [[double bond, length as m-dash]] O)–NH containing compounds

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Article information


Submitted
26 Jun 2017
Accepted
14 Jul 2017
First published
14 Jul 2017

Chem. Commun., 2017,53, 8667-8670
Article type
Communication

o-Phthalaldehyde catalyzed hydrolysis of organophosphinic amides and other P([double bond, length as m-dash]O)–NH containing compounds

B. Li, R. D. Simard and A. M. Beauchemin, Chem. Commun., 2017, 53, 8667
DOI: 10.1039/C7CC04950A

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