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

Research output: Contribution to journalArticle

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 languageEnglish
Pages (from-to)6366-6371
Number of pages6
JournalJournal of Organic Chemistry
Volume79
Issue number13
DOIs
Publication statusPublished - 3 Jul 2014

Fingerprint

Indoleamine-Pyrrole 2,3,-Dioxygenase
Palladium
Nanoparticles
Bearings (structural)
Chemical activation
Sulfur
Gold
benzotriazole

Cite this

@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 = "7",
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",

}

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; Wouters, Johan; Sugimoto, Hiroshi; Shiro, Yoshitsugu; Fukuda, Hayato; Shuto, Satoshi; Arisawa, Mitsuhiro.

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

Research output: Contribution to journalArticle

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

VL - 79

SP - 6366

EP - 6371

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

SN - 0022-3263

IS - 13

ER -