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

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...

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Published in:Chemical communications (Cambridge, England) England), 2017-08, Vol.53 (62), p.8667-8670
Main Authors: Li, Bin-Jie, Simard, Ryan D, Beauchemin, André M
Format: Article
Language:English
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Summary: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.
ISSN:1359-7345
1364-548X
DOI:10.1039/c7cc04950a