Complementary Synthetic Approaches toward 9-Phosphatriptycene and Structure-Reactivity Investigations of Its Association with Sterically Hindered Lewis Acids

Lei Hu; Damien Mahaut; Nikolay Tumanov; Johan Wouters; Raphaël Robiette; Guillaume Berionni

doi:10.1021/acs.joc.9b01570

Complementary Synthetic Approaches toward 9-Phosphatriptycene and Structure-Reactivity Investigations of Its Association with Sterically Hindered Lewis Acids

Lei Hu, Damien Mahaut, Nikolay Tumanov, Johan Wouters, Raphaël Robiette, Guillaume Berionni

Résultats de recherche: Contribution à un journal/une revue › Article › Revue par des pairs

Résumé

Two practical and high-yielding syntheses of 9-phosphatriptycene are reported. In both approaches, the key step is based on the cyclization of a (tris)lithio-triphenylmethane or a (tris)lithio-triphenylphosphine intermediate on a phosphorus or a carbon electrophile, respectively. The association of 9-phosphatriptycene with representative boron- and carbon-centered Lewis acids was investigated by IR, NMR, and UV-vis titration experiments and by computational methods, shedding light on its steric hindrance, σ-donating ability, and Brønsted and Lewis basicities.

langue originale	Anglais
Pages (de - à)	11268-11274
Nombre de pages	7
journal	Journal of Organic Chemistry
Volume	84
Numéro de publication	17
Les DOIs	https://doi.org/10.1021/acs.joc.9b01570
Etat de la publication	Publié - 6 sept. 2019

Accès au document

10.1021/acs.joc.9b01570

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Link to publication in Scopus

HydrogenActive: Hydrogénation d’alcènes non-activés, d’amides et du dioxyde de carbone par des catalyseurs de type paires de Lewis frustrées
Mahaut, D. (Responsable du Projet), Berionni, G. (Promoteur) & CHAMPAGNE, B. (Co-Promoteur)
1/10/19 → 1/10/23
Projet: Projet de thèse

Physico-chimie et caractérisation (PC2)
Wouters, J. (!!Manager), Aprile, C. (!!Manager) & Fusaro, L. (!!Manager)
Plateforme technologique Caracterisation physico-chimiques
Equipement/installations: Plateforme technolgique
Spectrométrie de masse (MASUN)
Renard, P. (!!Manager)
Plateforme technologique Proteomique et spectrometrie de masse
Equipement/installations: Plateforme technolgique

CCDC 1905040: Experimental Crystal Structure Determination
Hu, L. (Contributeur), Mahaut, D. (Contributeur), Tumanov, N. (Contributeur), Wouters, J. (Contributeur), Robiette, R. (Créateur) & Berionni, G. (Contributeur), University of Namur, 6 sept. 2019
DOI: 10.5517/ccdc.csd.cc21ybx8, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/ccdc.csd.cc21ybx8&sid=DataCite
Ensemble de données
CCDC 1905039: Experimental Crystal Structure Determination
Hu, L. (Contributeur), Mahaut, D. (Contributeur), Tumanov, N. (Contributeur), Wouters, J. (Contributeur), Robiette, R. (Créateur) & Berionni, G. (Contributeur), University of Namur, 6 sept. 2019
DOI: 10.5517/ccdc.csd.cc21ybw7, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/ccdc.csd.cc21ybw7&sid=DataCite
Ensemble de données
CCDC 1905043: Experimental Crystal Structure Determination
Hu, L. (Contributeur), Mahaut, D. (Contributeur), Tumanov, N. (Contributeur), Wouters, J. (Contributeur), Robiette, R. (Créateur) & Berionni, G. (Contributeur), University of Namur, 6 sept. 2019
DOI: 10.5517/ccdc.csd.cc21yc0d, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/ccdc.csd.cc21yc0d&sid=DataCite
Ensemble de données

Contient cette citation

@article{cf850de43969461b9760e9ead5472364,

title = "Complementary Synthetic Approaches toward 9-Phosphatriptycene and Structure-Reactivity Investigations of Its Association with Sterically Hindered Lewis Acids",

abstract = "Two practical and high-yielding syntheses of 9-phosphatriptycene are reported. In both approaches, the key step is based on the cyclization of a (tris)lithio-triphenylmethane or a (tris)lithio-triphenylphosphine intermediate on a phosphorus or a carbon electrophile, respectively. The association of 9-phosphatriptycene with representative boron- and carbon-centered Lewis acids was investigated by IR, NMR, and UV-vis titration experiments and by computational methods, shedding light on its steric hindrance, σ-donating ability, and Br{\o}nsted and Lewis basicities.",

author = "Lei Hu and Damien Mahaut and Nikolay Tumanov and Johan Wouters and Rapha{\"e}l Robiette and Guillaume Berionni",

note = "Funding Information: We acknowledge the University of Namur, the Namur Institute of Structured Matter (NISM), and the Fond National de la Recherche Scientifique FNRS (MIS grant F.4513.18 for G.B.) for generous funding. We thank the PC technological platform at the University of Namur for access to X-ray diffraction and NMR instruments. We thank Dr. Koen Robeyns (UCLouvain) for the help with refinement of 18 . Computational resources have been provided by the supercomputing facilities of the Universit{\'e} catholique de Louvain (CISM/UCL) and the Consortium des {\'E}quipements de Calcul Intensif en F{\'e}d{\'e}ration Wallonie Bruxelles (C{\'E}CI) funded by the FNRS under convention 2.5020.11 and by the Walloon Region. L.H. was supported through a Ph.D. grant from the China Scholarship Council (CSC, 201606670003). R.R. is a Ma{\^i}tre de Recherche of the F.R.S.-FNRS. 2 Publisher Copyright: {\textcopyright} 2019 American Chemical Society. Copyright: Copyright 2019 Elsevier B.V., All rights reserved.",

year = "2019",

month = sep,

day = "6",

doi = "10.1021/acs.joc.9b01570",

language = "English",

volume = "84",

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Complementary Synthetic Approaches toward 9-Phosphatriptycene and Structure-Reactivity Investigations of Its Association with Sterically Hindered Lewis Acids. / Hu, Lei ; Mahaut, Damien ; Tumanov, Nikolay et al.
Dans: Journal of Organic Chemistry, Vol 84, Numéro 17, 06.09.2019, p. 11268-11274.

Résultats de recherche: Contribution à un journal/une revue › Article › Revue par des pairs

TY - JOUR

T1 - Complementary Synthetic Approaches toward 9-Phosphatriptycene and Structure-Reactivity Investigations of Its Association with Sterically Hindered Lewis Acids

AU - Hu, Lei

AU - Mahaut, Damien

AU - Tumanov, Nikolay

AU - Wouters, Johan

AU - Robiette, Raphaël

AU - Berionni, Guillaume

N1 - Funding Information: We acknowledge the University of Namur, the Namur Institute of Structured Matter (NISM), and the Fond National de la Recherche Scientifique FNRS (MIS grant F.4513.18 for G.B.) for generous funding. We thank the PC technological platform at the University of Namur for access to X-ray diffraction and NMR instruments. We thank Dr. Koen Robeyns (UCLouvain) for the help with refinement of 18 . Computational resources have been provided by the supercomputing facilities of the Université catholique de Louvain (CISM/UCL) and the Consortium des Équipements de Calcul Intensif en Fédération Wallonie Bruxelles (CÉCI) funded by the FNRS under convention 2.5020.11 and by the Walloon Region. L.H. was supported through a Ph.D. grant from the China Scholarship Council (CSC, 201606670003). R.R. is a Maître de Recherche of the F.R.S.-FNRS. 2 Publisher Copyright: © 2019 American Chemical Society. Copyright: Copyright 2019 Elsevier B.V., All rights reserved.

PY - 2019/9/6

Y1 - 2019/9/6

N2 - Two practical and high-yielding syntheses of 9-phosphatriptycene are reported. In both approaches, the key step is based on the cyclization of a (tris)lithio-triphenylmethane or a (tris)lithio-triphenylphosphine intermediate on a phosphorus or a carbon electrophile, respectively. The association of 9-phosphatriptycene with representative boron- and carbon-centered Lewis acids was investigated by IR, NMR, and UV-vis titration experiments and by computational methods, shedding light on its steric hindrance, σ-donating ability, and Brønsted and Lewis basicities.

AB - Two practical and high-yielding syntheses of 9-phosphatriptycene are reported. In both approaches, the key step is based on the cyclization of a (tris)lithio-triphenylmethane or a (tris)lithio-triphenylphosphine intermediate on a phosphorus or a carbon electrophile, respectively. The association of 9-phosphatriptycene with representative boron- and carbon-centered Lewis acids was investigated by IR, NMR, and UV-vis titration experiments and by computational methods, shedding light on its steric hindrance, σ-donating ability, and Brønsted and Lewis basicities.

UR - https://pubs.acs.org/doi/10.1021/acs.joc.9b01570

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DO - 10.1021/acs.joc.9b01570

M3 - Article

C2 - 31385508

AN - SCOPUS:85071957224

SN - 0022-3263

VL - 84

SP - 11268

EP - 11274

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

IS - 17

ER -

Complementary Synthetic Approaches toward 9-Phosphatriptycene and Structure-Reactivity Investigations of Its Association with Sterically Hindered Lewis Acids

Résumé

Accès au document

Autres fichiers et liens

Empreinte digitale

Projets

HydrogenActive: Hydrogénation d’alcènes non-activés, d’amides et du dioxyde de carbone par des catalyseurs de type paires de Lewis frustrées

Équipement

Physico-chimie et caractérisation (PC2)

Spectrométrie de masse (MASUN)

Ensembles de données

CCDC 1905040: Experimental Crystal Structure Determination

CCDC 1905039: Experimental Crystal Structure Determination

CCDC 1905043: Experimental Crystal Structure Determination

Contient cette citation