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Defying Stereotypes with Nanodiamonds: Stable Primary Diamondoid Phosphines

Oana Moncea 1, 2 Maria A. Gunawan 1, 2 Didier Poinsot 1 Hélène Cattey 1 Jonathan Becker 3 Raisa I. Yurchenko 4 Ekaterina D. Butova 4 Heike Hausmann 2 Marina Šekutor 2 Andrey A. Fokin 4, 2, * Jean-Cyrille Hierso 5, 1, * Peter R. Schreiner 2, *
* Auteur correspondant
1 ICMUB - Institut de Chimie Moléculaire de l'Université de Bourgogne [Dijon]
2 Institut für Organische Chemie, Justus-Liebig-Universität
3 Institut für Anorganische und Analytische Chemie, Justus-Liebig-Universität
4 Department of Organic Chemistry
5 IUF - Institut Universitaire de France
Abstract : Direct unequal C-H bond difunctionalization of phosphorylated diamantane was achieved in high yield from the corresponding phosphonates. Reduction of the functionalized phosphonates provides access to novel primary and secondary alkyl/aryl diamantane phosphines. The prepared primary diamantyl phosphines are quite air stable compared to their adamantyl and especially alkyl or aryl analogues. This finding is corroborated by comparing the singly occupied molecular orbital energy levels of the corresponding phosphine radical cations obtained by density functional theory computations.
Keywords : deactivated aryl chlorides room-temperature phosphorylated adamantanes homogeneous catalysts selective preparation molecular tripod palladium ligands chemistry arylation
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https://hal-univ-bourgogne.archives-ouvertes.fr/hal-01399442
Contributeur : Icmub - Université de Bourgogne <>
Soumis le : vendredi 18 novembre 2016 - 19:02:07
Dernière modification le : dimanche 23 juin 2019 - 11:00:03

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UNIV-BOURGOGNE | CNRS | INC-CNRS | ICMUB

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Oana Moncea, Maria A. Gunawan, Didier Poinsot, Hélène Cattey, Jonathan Becker, et al.. Defying Stereotypes with Nanodiamonds: Stable Primary Diamondoid Phosphines. Journal of Organic Chemistry, American Chemical Society, 2016, 81 (19), pp.8759 - 8769. ⟨10.1021/acs.joc.6b01219⟩. ⟨hal-01399442⟩

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