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

Unit of theoretical and structural physico-chemistry

Research output: Contribution to journal › Article › peer-review

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.

Original language	English
Pages (from-to)	6366-6371
Number of pages	6
Journal	Journal of Organic Chemistry
Volume	79
Issue number	13
DOIs	https://doi.org/10.1021/jo5009838
Publication status	Published - 3 Jul 2014

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Physical Chemistry and characterization(PC2)
Wouters, J. (Manager), Aprile, C. (Manager) & Fusaro, L. (Manager)
Technological Platform Physical Chemistry and characterization
Facility/equipment: Technological Platform

CCDC 999300: Experimental Crystal Structure Determination
Al-Amin, M. (Contributor), Arisawa, M. (Contributor), Fukuda, H. (Contributor), Hoshiya, N. (Contributor), Shiro, Y. (Contributor), Shuto, S. (Contributor), Sugimoto, H. (Contributor), Takagi, K. (Contributor) & Wouters, J. (Contributor), Cambridge Crystallographic Data Centre, 1 Jan 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. In: Journal of Organic Chemistry. 2014 ; Vol. 79, No. 13. pp. 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",

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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, vol. 79, no. 13, pp. 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.
In: Journal of Organic Chemistry, Vol. 79, No. 13, 03.07.2014, p. 6366-6371.

Research output: Contribution to journal › Article › peer-review

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

M3 - Article

C2 - 24906179

AN - SCOPUS:84903742359

SN - 0022-3263

VL - 79

SP - 6366

EP - 6371

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 Jul 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

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CCDC 999300: Experimental Crystal Structure Determination

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