Catalyst-free hydrophosphinylation of isocyanates and isothiocyanates under low-added-solvent conditions

Huke, Cameron D., Taylor, Laurence J., Argent, Stephen P. and Kays, Deborah L. ORCID: https://orcid.org/0000-0002-4616-6001 2021. Catalyst-free hydrophosphinylation of isocyanates and isothiocyanates under low-added-solvent conditions. ACS Sustainable Chemistry & Engineering 9 (32) , 10704–10709. 10.1021/acssuschemeng.1c02907

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Abstract

A catalyst-free, low-solvent method for the hydrophosphinylation of isocyanates and isothiocyanates is reported. A range of phosphorus nucleophiles including secondary phosphine oxides HP(O)R2 (R = Ph, iPr), phosphites HP(O)(OR)2 (R = Me, Et), and methyl phenylphosphinate were tested. The procedure tolerated isocyanates and isothiocyanates featuring a wide range of substituents and, with use of 4 equiv of 2-methyltetrahydrofuran (2-MeTHF), solid substrates can be utilized. Twenty-five compounds were prepared with improved functional group tolerance compared to previous methods allowing access to new compounds (16 are novel). Facile scale up and simple reaction conditions make this a straightforward and practical methodology for obtaining phosphorus analogues of ureas and thioureas, which are challenging to synthesize by other methods.

Item Type:	Article
Date Type:	Publication
Status:	Published
Schools:	Chemistry
Publisher:	ACS Publications
ISSN:	2168-0485
Date of First Compliant Deposit:	12 July 2024
Date of Acceptance:	3 August 2021
Last Modified:	07 Aug 2024 08:59
URI:	https://orca.cardiff.ac.uk/id/eprint/170309

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