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Catalyst-free Hydrophosphinylation of Isocyanates and Isothiocyanates under Low-Added-Solvent Conditions

Huke, Cameron D.; Taylor, Laurence J.; Argent, Stephen P.; Kays, Deborah L.

Catalyst-free Hydrophosphinylation of Isocyanates and Isothiocyanates under Low-Added-Solvent Conditions Thumbnail


Authors

Cameron D. Huke

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LAURENCE TAYLOR Laurence.Taylor@nottingham.ac.uk
Teaching Associate in Organic Chemistry

DEBORAH KAYS DEBORAH.KAYS@NOTTINGHAM.AC.UK
Professor of Inorganic Chemistry



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.

Citation

Huke, C. D., Taylor, L. J., Argent, S. P., & Kays, D. L. (2021). Catalyst-free Hydrophosphinylation of Isocyanates and Isothiocyanates under Low-Added-Solvent Conditions. ACS Sustainable Chemistry and Engineering, 9(32), 10704-10709. https://doi.org/10.1021/acssuschemeng.1c02907

Journal Article Type Article
Acceptance Date Jun 11, 2021
Online Publication Date Aug 3, 2021
Publication Date Aug 16, 2021
Deposit Date Jun 25, 2021
Publicly Available Date Aug 3, 2021
Journal ACS Sustainable Chemistry and Engineering
Electronic ISSN 2168-0485
Publisher American Chemical Society
Peer Reviewed Peer Reviewed
Volume 9
Issue 32
Pages 10704-10709
DOI https://doi.org/10.1021/acssuschemeng.1c02907
Keywords Renewable Energy, Sustainability and the Environment; General Chemical Engineering; Environmental Chemistry; General Chemistry; Hydrophosphinylation; Hydrophosphonylation; Atom-efficient; Metal-free; Heterocumulene; Carboxamide; Thiocarboxamide
Public URL https://nottingham-repository.worktribe.com/output/5722612
Publisher URL https://pubs.acs.org/doi/abs/10.1021/acssuschemeng.1c02907

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