Palladium-nanoparticle-catalyzed 1,7-palladium migration involving C-H activation, followed by intramolecular lamination: Regioselective synthesis of N 1-arylbenzotriazoles and an evaluation of their inhibitory activity toward indoleamine 2,3-dioxygenase

Koji Takagi; Mohammad Al-Amin; Naoyuki Hoshiya; Johan Wouters; Hiroshi Sugimoto; Yoshitsugu Shiro; Hayato Fukuda; Satoshi Shuto; Mitsuhiro Arisawa

doi:10.1021/jo5009838

Palladium-nanoparticle-catalyzed 1,7-palladium migration involving C-H activation, followed by intramolecular lamination: Regioselective synthesis of N 1-arylbenzotriazoles and an evaluation of their inhibitory activity toward indoleamine 2,3-dioxygenase

Koji Takagi, Mohammad Al-Amin, Naoyuki Hoshiya, Johan Wouters, Hiroshi Sugimoto, Yoshitsugu Shiro, Hayato Fukuda, Satoshi Shuto, Mitsuhiro Arisawa

Unite de recherche en chimie physique, theorique et structurale

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

Résumé

A sulfur-modified gold-supported palladium material (SAPd) has been developed bearing palladium nanoparticles on its surface. Herein, we report for the first time the use of SAPd to affect a Pd-nanoparticle-catalyzed 1,7-Pd migration reaction for the synthesis of benzotriazoles via C-H bond activation. The resulting benzotriazoles were evaluated in terms of their inhibitory activity toward indoleamine 2,3-dioxygenase.

langue originale	Anglais
Pages (de - à)	6366-6371
Nombre de pages	6
journal	Journal of Organic Chemistry
Volume	79
Numéro de publication	13
Les DOIs	https://doi.org/10.1021/jo5009838
Etat de la publication	Publié - 3 juil. 2014

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10.1021/jo5009838

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CCDC 999300: Experimental Crystal Structure Determination
Al-Amin, M. (Contributeur), Arisawa, M. (Contributeur), Fukuda, H. (Contributeur), Hoshiya, N. (Contributeur), Shiro, Y. (Contributeur), Shuto, S. (Contributeur), Sugimoto, H. (Contributeur), Takagi, K. (Contributeur) & Wouters, J. (Contributeur), Cambridge Crystallographic Data Centre, 1 janv. 2014
DOI: 10.5517/cc12jvhy, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/cc12jvhy&sid=DataCite
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Takagi, K., Al-Amin, M., Hoshiya, N., Wouters, J., Sugimoto, H., Shiro, Y., Fukuda, H., Shuto, S., & Arisawa, M. (2014). Palladium-nanoparticle-catalyzed 1,7-palladium migration involving C-H activation, followed by intramolecular lamination: Regioselective synthesis of N 1-arylbenzotriazoles and an evaluation of their inhibitory activity toward indoleamine 2,3-dioxygenase. Journal of Organic Chemistry, 79(13), 6366-6371. https://doi.org/10.1021/jo5009838

Takagi, Koji ; Al-Amin, Mohammad ; Hoshiya, Naoyuki et al. / Palladium-nanoparticle-catalyzed 1,7-palladium migration involving C-H activation, followed by intramolecular lamination: Regioselective synthesis of N 1-arylbenzotriazoles and an evaluation of their inhibitory activity toward indoleamine 2,3-dioxygenase. Dans: Journal of Organic Chemistry. 2014 ; Vol 79, Numéro 13. p. 6366-6371.

@article{875a21d039ce4be8bc66d375e98b064a,

title = "Palladium-nanoparticle-catalyzed 1,7-palladium migration involving C-H activation, followed by intramolecular lamination: Regioselective synthesis of N 1-arylbenzotriazoles and an evaluation of their inhibitory activity toward indoleamine 2,3-dioxygenase",

abstract = "A sulfur-modified gold-supported palladium material (SAPd) has been developed bearing palladium nanoparticles on its surface. Herein, we report for the first time the use of SAPd to affect a Pd-nanoparticle-catalyzed 1,7-Pd migration reaction for the synthesis of benzotriazoles via C-H bond activation. The resulting benzotriazoles were evaluated in terms of their inhibitory activity toward indoleamine 2,3-dioxygenase.",

author = "Koji Takagi and Mohammad Al-Amin and Naoyuki Hoshiya and Johan Wouters and Hiroshi Sugimoto and Yoshitsugu Shiro and Hayato Fukuda and Satoshi Shuto and Mitsuhiro Arisawa",

year = "2014",

month = jul,

day = "3",

doi = "10.1021/jo5009838",

language = "English",

volume = "79",

pages = "6366--6371",

journal = "Journal of Organic Chemistry",

issn = "0022-3263",

publisher = "American Chemical Society",

number = "13",

}

Takagi, K, Al-Amin, M, Hoshiya, N, Wouters, J, Sugimoto, H, Shiro, Y, Fukuda, H, Shuto, S & Arisawa, M 2014, 'Palladium-nanoparticle-catalyzed 1,7-palladium migration involving C-H activation, followed by intramolecular lamination: Regioselective synthesis of N 1-arylbenzotriazoles and an evaluation of their inhibitory activity toward indoleamine 2,3-dioxygenase', Journal of Organic Chemistry, VOL. 79, Numéro 13, p. 6366-6371. https://doi.org/10.1021/jo5009838

Palladium-nanoparticle-catalyzed 1,7-palladium migration involving C-H activation, followed by intramolecular lamination: Regioselective synthesis of N 1-arylbenzotriazoles and an evaluation of their inhibitory activity toward indoleamine 2,3-dioxygenase. / Takagi, Koji; Al-Amin, Mohammad; Hoshiya, Naoyuki et al.
Dans: Journal of Organic Chemistry, Vol 79, Numéro 13, 03.07.2014, p. 6366-6371.

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

TY - JOUR

T1 - Palladium-nanoparticle-catalyzed 1,7-palladium migration involving C-H activation, followed by intramolecular lamination: Regioselective synthesis of N 1-arylbenzotriazoles and an evaluation of their inhibitory activity toward indoleamine 2,3-dioxygenase

AU - Takagi, Koji

AU - Al-Amin, Mohammad

AU - Hoshiya, Naoyuki

AU - Wouters, Johan

AU - Sugimoto, Hiroshi

AU - Shiro, Yoshitsugu

AU - Fukuda, Hayato

AU - Shuto, Satoshi

AU - Arisawa, Mitsuhiro

PY - 2014/7/3

Y1 - 2014/7/3

N2 - A sulfur-modified gold-supported palladium material (SAPd) has been developed bearing palladium nanoparticles on its surface. Herein, we report for the first time the use of SAPd to affect a Pd-nanoparticle-catalyzed 1,7-Pd migration reaction for the synthesis of benzotriazoles via C-H bond activation. The resulting benzotriazoles were evaluated in terms of their inhibitory activity toward indoleamine 2,3-dioxygenase.

AB - A sulfur-modified gold-supported palladium material (SAPd) has been developed bearing palladium nanoparticles on its surface. Herein, we report for the first time the use of SAPd to affect a Pd-nanoparticle-catalyzed 1,7-Pd migration reaction for the synthesis of benzotriazoles via C-H bond activation. The resulting benzotriazoles were evaluated in terms of their inhibitory activity toward indoleamine 2,3-dioxygenase.

UR - http://www.scopus.com/inward/record.url?scp=84903742359&partnerID=8YFLogxK

U2 - 10.1021/jo5009838

DO - 10.1021/jo5009838

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AN - SCOPUS:84903742359

SN - 0022-3263

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JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

IS - 13

ER -

Takagi K, Al-Amin M, Hoshiya N, Wouters J, Sugimoto H, Shiro Y et al. Palladium-nanoparticle-catalyzed 1,7-palladium migration involving C-H activation, followed by intramolecular lamination: Regioselective synthesis of N 1-arylbenzotriazoles and an evaluation of their inhibitory activity toward indoleamine 2,3-dioxygenase. Journal of Organic Chemistry. 2014 juil. 3;79(13):6366-6371. doi: 10.1021/jo5009838

Palladium-nanoparticle-catalyzed 1,7-palladium migration involving C-H activation, followed by intramolecular lamination: Regioselective synthesis of N 1-arylbenzotriazoles and an evaluation of their inhibitory activity toward indoleamine 2,3-dioxygenase

Résumé

Accès au document

Autres fichiers et liens

Empreinte digitale

Équipement

Physico-chimie et caractérisation (PC2)

Ensembles de données

CCDC 999300: Experimental Crystal Structure Determination

Contient cette citation