P–C bond formation via P–H addition of a fluoroaryl phosphinic acid to ketones

The synthesis, structure and reactivity of the fluoroaryl phosphinic acid HF(4)C(6)–P(O)HOH is reported and compared to a sterically comparable yet non-fluorinated analog with similar size. The fluoroaryl phosphinic acid undergoes reversible P–H addition to the carbonyl functionality of ketones unde...

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Detalles Bibliográficos
Autores principales: Orthaber, Andreas, Albering, Jörg H., Belaj, Ferdinand, Pietschnig, Rudolf
Formato: Texto
Lenguaje:English
Publicado: Elsevier Sequoia Sa 2010
Materias:
Article
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2954306/
https://www.ncbi.nlm.nih.gov/pubmed/21072125
http://dx.doi.org/10.1016/j.jfluchem.2010.07.008
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author Orthaber, Andreas
Albering, Jörg H.
Belaj, Ferdinand
Pietschnig, Rudolf
author_facet Orthaber, Andreas
Albering, Jörg H.
Belaj, Ferdinand
Pietschnig, Rudolf
author_sort Orthaber, Andreas
collection PubMed
description The synthesis, structure and reactivity of the fluoroaryl phosphinic acid HF(4)C(6)–P(O)HOH is reported and compared to a sterically comparable yet non-fluorinated analog with similar size. The fluoroaryl phosphinic acid undergoes reversible P–H addition to the carbonyl functionality of ketones under formation of a P–C bond which is retained in the resulting α-hydroxy phosphinic acid. The latter shows an extended 2D hydrogen bonded network in the solid state.
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spelling pubmed-29543062010-11-08 P–C bond formation via P–H addition of a fluoroaryl phosphinic acid to ketones Orthaber, Andreas Albering, Jörg H. Belaj, Ferdinand Pietschnig, Rudolf J Fluor Chem Article The synthesis, structure and reactivity of the fluoroaryl phosphinic acid HF(4)C(6)–P(O)HOH is reported and compared to a sterically comparable yet non-fluorinated analog with similar size. The fluoroaryl phosphinic acid undergoes reversible P–H addition to the carbonyl functionality of ketones under formation of a P–C bond which is retained in the resulting α-hydroxy phosphinic acid. The latter shows an extended 2D hydrogen bonded network in the solid state. Elsevier Sequoia Sa 2010-10 /pmc/articles/PMC2954306/ /pubmed/21072125 http://dx.doi.org/10.1016/j.jfluchem.2010.07.008 Text en © 2010 Elsevier B.V. https://creativecommons.org/licenses/by-nc-nd/3.0/Open Access under CC BY-NC-ND 3.0 (https://creativecommons.org/licenses/by-nc-nd/3.0/) license
spellingShingle Article
Orthaber, Andreas
Albering, Jörg H.
Belaj, Ferdinand
Pietschnig, Rudolf
P–C bond formation via P–H addition of a fluoroaryl phosphinic acid to ketones
title P–C bond formation via P–H addition of a fluoroaryl phosphinic acid to ketones
title_full P–C bond formation via P–H addition of a fluoroaryl phosphinic acid to ketones
title_fullStr P–C bond formation via P–H addition of a fluoroaryl phosphinic acid to ketones
title_full_unstemmed P–C bond formation via P–H addition of a fluoroaryl phosphinic acid to ketones
title_short P–C bond formation via P–H addition of a fluoroaryl phosphinic acid to ketones
title_sort p–c bond formation via p–h addition of a fluoroaryl phosphinic acid to ketones
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2954306/
https://www.ncbi.nlm.nih.gov/pubmed/21072125
http://dx.doi.org/10.1016/j.jfluchem.2010.07.008
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AT alberingjorgh pcbondformationviaphadditionofafluoroarylphosphinicacidtoketones
AT belajferdinand pcbondformationviaphadditionofafluoroarylphosphinicacidtoketones
AT pietschnigrudolf pcbondformationviaphadditionofafluoroarylphosphinicacidtoketones

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