Synthesis of Tertiary Enamides by Ag2CO3-Promoted Pd-Catalyzed Alkenylation of Acyclic Secondary Amides

Arnaud Delforge; Irene Georgiou; Adrian Kremer; Johan Wouters; Davide Bonifazi

doi:10.1021/acs.orglett.6b02305

Synthesis of Tertiary Enamides by Ag₂CO₃-Promoted Pd-Catalyzed Alkenylation of Acyclic Secondary Amides

Arnaud Delforge, Irene Georgiou, Adrian Kremer, Johan Wouters, Davide Bonifazi

Universite de Namur

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

Résumé

A Pd-catalyzed methodology for the preparation of tertiary enamides from acyclic secondary amides and bromo acrylates under mild reaction conditions has been developed using [Pd₂(dba)₃], XantPhos, and Ag₂CO₃ as a base. The reaction occurs through a stereospecific metal-mediated oxidative-insertion mechanism.

langue originale	Anglais
Pages (de - à)	4844-4847
Nombre de pages	4
journal	Organic Letters
Volume	18
Numéro de publication	19
Les DOIs	https://doi.org/10.1021/acs.orglett.6b02305
Etat de la publication	Publié - 7 oct. 2016

Accès au document

10.1021/acs.orglett.6b02305

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Link to publication in Scopus

Physico-chimie et caractérisation (PC2)
Johan Wouters (!!Manager) & Carmela Aprile (!!Manager)
Plateforme technologique Caracterisation physico-chimiques
Equipement/installations: Plateforme technolgique

CCDC 1014016: Experimental Crystal Structure Determination
Delforge, A. (Contributeur), Georgiou, I. (Contributeur), Kremer, A. (Contributeur), Wouters, J. (Contributeur) & BONIFAZI, D. (Contributeur), University of Namur, 7 oct. 2016
DOI: 10.5517/ccdc.csd.cc13156j, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/ccdc.csd.cc13156j&sid=DataCite
Ensemble de données
CCDC 1410566: Experimental Crystal Structure Determination
Delforge, A. (Contributeur), Georgiou, I. (Contributeur), Kremer, A. (Contributeur), Wouters, J. (Contributeur) & BONIFAZI, D. (Contributeur), University of Namur, 7 oct. 2016
DOI: 10.5517/ccdc.csd.cc1jbt4t, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/ccdc.csd.cc1jbt4t&sid=DataCite
Ensemble de données
CCDC 1014015: Experimental Crystal Structure Determination
Delforge, A. (Contributeur), Georgiou, I. (Contributeur), Kremer, A. (Contributeur), Wouters, J. (Contributeur) & BONIFAZI, D. (Contributeur), University of Namur, 7 oct. 2016
DOI: 10.5517/ccdc.csd.cc13155h, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/ccdc.csd.cc13155h&sid=DataCite
Ensemble de données

Contient cette citation

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title = "Synthesis of Tertiary Enamides by Ag2CO3-Promoted Pd-Catalyzed Alkenylation of Acyclic Secondary Amides",

abstract = "A Pd-catalyzed methodology for the preparation of tertiary enamides from acyclic secondary amides and bromo acrylates under mild reaction conditions has been developed using [Pd2(dba)3], XantPhos, and Ag2CO3 as a base. The reaction occurs through a stereospecific metal-mediated oxidative-insertion mechanism.",

author = "Arnaud Delforge and Irene Georgiou and Adrian Kremer and Johan Wouters and Davide Bonifazi",

year = "2016",

month = oct,

day = "7",

doi = "10.1021/acs.orglett.6b02305",

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volume = "18",

pages = "4844--4847",

journal = "Organic Letters",

issn = "1523-7060",

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T1 - Synthesis of Tertiary Enamides by Ag2CO3-Promoted Pd-Catalyzed Alkenylation of Acyclic Secondary Amides

AU - Delforge, Arnaud

AU - Georgiou, Irene

AU - Kremer, Adrian

AU - Wouters, Johan

AU - Bonifazi, Davide

PY - 2016/10/7

Y1 - 2016/10/7

N2 - A Pd-catalyzed methodology for the preparation of tertiary enamides from acyclic secondary amides and bromo acrylates under mild reaction conditions has been developed using [Pd2(dba)3], XantPhos, and Ag2CO3 as a base. The reaction occurs through a stereospecific metal-mediated oxidative-insertion mechanism.

AB - A Pd-catalyzed methodology for the preparation of tertiary enamides from acyclic secondary amides and bromo acrylates under mild reaction conditions has been developed using [Pd2(dba)3], XantPhos, and Ag2CO3 as a base. The reaction occurs through a stereospecific metal-mediated oxidative-insertion mechanism.

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U2 - 10.1021/acs.orglett.6b02305

DO - 10.1021/acs.orglett.6b02305

M3 - Article

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SN - 1523-7060

VL - 18

SP - 4844

EP - 4847

JO - Organic Letters

JF - Organic Letters

IS - 19

ER -

Synthesis of Tertiary Enamides by Ag2CO3-Promoted Pd-Catalyzed Alkenylation of Acyclic Secondary Amides

Résumé

Accès au document

Autres fichiers et liens

Empreinte digitale

Équipement

Physico-chimie et caractérisation (PC2)

Ensembles de données

CCDC 1014016: Experimental Crystal Structure Determination

CCDC 1410566: Experimental Crystal Structure Determination

CCDC 1014015: Experimental Crystal Structure Determination

Contient cette citation

Synthesis of Tertiary Enamides by Ag₂CO₃-Promoted Pd-Catalyzed Alkenylation of Acyclic Secondary Amides