Scope and Mechanisms of Frustrated Lewis Pair Catalyzed Hydrogenation Reactions of Electron-Deficient C£C Double Bonds

Varvara Morozova; Peter Mayer; Guillaume Berionni

doi:10.1002/anie.201507298

Scope and Mechanisms of Frustrated Lewis Pair Catalyzed Hydrogenation Reactions of Electron-Deficient C£C Double Bonds

Varvara Morozova, Peter Mayer, Guillaume Berionni

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

Résumé

Several phosphonium and ammonium triarylborohydrides, which are intermediates in hydrogenation reactions catalyzed by frustrated Lewis pairs, were synthesized in high yield under mild conditions from triaryl boranes, ammonium or phosphonium halides, and triethylsilane. The kinetics and mechanisms of the reactions of these hydridoborate salts with benzhydrylium ions, iminium ions, quinone methides, and Michael acceptors were investigated, and their nucleophilicity was determined and compared with that of other hydride donors.

langue originale	Anglais
Pages (de - à)	14508-14512
Nombre de pages	5
journal	Angewandte Chemie - International Edition
Volume	54
Numéro de publication	48
Les DOIs	https://doi.org/10.1002/anie.201507298
Etat de la publication	Publié - 23 nov. 2015
Modification externe	Oui

Accès au document

10.1002/anie.201507298

Autres fichiers et liens

Link to publication in Scopus

CCDC 1413310: Experimental Crystal Structure Determination
Berionni, G. (Contributeur), Mayer, P. (Contributeur) & Morozova, V. (Contributeur), Cambridge Crystallographic Data Centre, 1 janv. 2016
DOI: 10.5517/cc1jfnn8, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/cc1jfnn8&sid=DataCite
Ensemble de données
CCDC 1413312: Experimental Crystal Structure Determination
Berionni, G. (Contributeur), Mayer, P. (Contributeur) & Morozova, V. (Contributeur), Cambridge Crystallographic Data Centre, 1 janv. 2016
DOI: 10.5517/cc1jfnqb, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/cc1jfnqb&sid=DataCite
Ensemble de données
CCDC 1413309: Experimental Crystal Structure Determination
Berionni, G. (Contributeur), Mayer, P. (Contributeur) & Morozova, V. (Contributeur), Cambridge Crystallographic Data Centre, 1 janv. 2016
DOI: 10.5517/cc1jfnm7, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/cc1jfnm7&sid=DataCite
Ensemble de données

Contient cette citation

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title = "Scope and Mechanisms of Frustrated Lewis Pair Catalyzed Hydrogenation Reactions of Electron-Deficient C£C Double Bonds",

abstract = "Several phosphonium and ammonium triarylborohydrides, which are intermediates in hydrogenation reactions catalyzed by frustrated Lewis pairs, were synthesized in high yield under mild conditions from triaryl boranes, ammonium or phosphonium halides, and triethylsilane. The kinetics and mechanisms of the reactions of these hydridoborate salts with benzhydrylium ions, iminium ions, quinone methides, and Michael acceptors were investigated, and their nucleophilicity was determined and compared with that of other hydride donors.",

keywords = "frustrated Lewis pairs, hydride donors, kinetics, nucleophilicity, reaction mechanisms",

author = "Varvara Morozova and Peter Mayer and Guillaume Berionni",

year = "2015",

month = nov,

day = "23",

doi = "10.1002/anie.201507298",

language = "English",

volume = "54",

pages = "14508--14512",

journal = "Angewandte Chemie - International Edition",

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Scope and Mechanisms of Frustrated Lewis Pair Catalyzed Hydrogenation Reactions of Electron-Deficient C£C Double Bonds. / Morozova, Varvara; Mayer, Peter; Berionni, Guillaume.
Dans: Angewandte Chemie - International Edition, Vol 54, Numéro 48, 23.11.2015, p. 14508-14512.

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

TY - JOUR

T1 - Scope and Mechanisms of Frustrated Lewis Pair Catalyzed Hydrogenation Reactions of Electron-Deficient C£C Double Bonds

AU - Morozova, Varvara

AU - Mayer, Peter

AU - Berionni, Guillaume

PY - 2015/11/23

Y1 - 2015/11/23

N2 - Several phosphonium and ammonium triarylborohydrides, which are intermediates in hydrogenation reactions catalyzed by frustrated Lewis pairs, were synthesized in high yield under mild conditions from triaryl boranes, ammonium or phosphonium halides, and triethylsilane. The kinetics and mechanisms of the reactions of these hydridoborate salts with benzhydrylium ions, iminium ions, quinone methides, and Michael acceptors were investigated, and their nucleophilicity was determined and compared with that of other hydride donors.

AB - Several phosphonium and ammonium triarylborohydrides, which are intermediates in hydrogenation reactions catalyzed by frustrated Lewis pairs, were synthesized in high yield under mild conditions from triaryl boranes, ammonium or phosphonium halides, and triethylsilane. The kinetics and mechanisms of the reactions of these hydridoborate salts with benzhydrylium ions, iminium ions, quinone methides, and Michael acceptors were investigated, and their nucleophilicity was determined and compared with that of other hydride donors.

KW - frustrated Lewis pairs

KW - hydride donors

KW - kinetics

KW - nucleophilicity

KW - reaction mechanisms

UR - http://www.scopus.com/inward/record.url?scp=84954404641&partnerID=8YFLogxK

U2 - 10.1002/anie.201507298

DO - 10.1002/anie.201507298

M3 - Article

AN - SCOPUS:84954404641

SN - 1433-7851

VL - 54

SP - 14508

EP - 14512

JO - Angewandte Chemie - International Edition

JF - Angewandte Chemie - International Edition

IS - 48

ER -

Scope and Mechanisms of Frustrated Lewis Pair Catalyzed Hydrogenation Reactions of Electron-Deficient C£C Double Bonds

Résumé

Accès au document

Autres fichiers et liens

Empreinte digitale

Ensembles de données

CCDC 1413310: Experimental Crystal Structure Determination

CCDC 1413312: Experimental Crystal Structure Determination

CCDC 1413309: Experimental Crystal Structure Determination

Contient cette citation