Defying Stereotypes with Nanodiamonds: Stable Primary Diamondoid Phosphines

Oana Moncea; Maria A. Gunawan; Didier Poinsot; Hélène Cattey; Jonathan Becker; Raisa I. Yurchenko; Ekaterina D. Butova; Heike Hausmann; Marina Šekutor; Andrey A. Fokin; Jean-Cyrille Hierso; Peter R. Schreiner

doi:10.1021/acs.joc.6b01219

Article dans une revue

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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Article dans une revue

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Chimie

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https://hal-univ-bourgogne.archives-ouvertes.fr/hal-01399442
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Soumis le : vendredi 18 novembre 2016 - 19:02:07
Dernière modification le : jeudi 16 décembre 2021 - 03:55:56

Defying Stereotypes with Nanodiamonds: Stable Primary Diamondoid Phosphines

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