Improving Robustness: In Situ Generation of a Pd(0) Catalyst for the Cyanation of Aryl Bromides

被引：30

作者：

Coombs, John R. ^{[1
]}

Fraunhoffer, Kenneth J. ^{[1
]}

Simmons, Eric M. ^{[1
]}

Stevens, Jason M. ^{[1
]}

Wisniewski, Steven R. ^{[1
]}

Yu, Miao ^{[1
]}

机构：

[1] Bristol Myers Squibb, Chem & Synthet Dev, 1 Squibb Dr, New Brunswick, NJ 08903 USA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2017年 / 82卷 / 13期

关键词：

POTASSIUM HEXACYANOFERRATE(II); PALLADIUM; HALIDES; NITRILES; CHLORIDES; AGENT; MILD; BENZONITRILES; HALOARENES; SYSTEM;

D O I：

10.1021/acs.joc.7b01003

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Conditions have been developed for the palladium-catalyzed cyanation of aryl bromides utilizing the air-stable XantPhos-PdCl2 precatalyst. By employing a trialkylamine as a reducing agent, the active Pd(0) species is generated in situ, alleviating the need to employ the air-sensitive Pd-2(dba)(3). Twenty-two substituted benzonitriles have been synthesized using this method.

引用

页码：7040 / 7044

页数：5

共 41 条

[1] Recent developments and perspectives in palladium-catalyzed cyanation of aryl halides: synthesis of benzonitriles [J].

Anbarasan, Pazhamalai ;

Schareina, Thomas ;

Beller, Matthias .

CHEMICAL SOCIETY REVIEWS, 2011, 40 (10) :5049-5067

[2] A Convenient Synthesis of Benzonitriles via Electrophilic Cyanation with N-Cyanobenzimidazole [J].

Anbarasan, Pazhamalai ;

Neumann, Helfried ;

Beller, Matthias .

CHEMISTRY-A EUROPEAN JOURNAL, 2010, 16 (16) :4725-4728

[3] A Homogeneous Method for the Conveniently Scalable Palladium- and Nickel-Catalyzed Cyanation of Aryl Halides [J].

Burg, Finn ;

Egger, Julian ;

Deutsch, Johannes ;

Guimond, Nicolas .

ORGANIC PROCESS RESEARCH & DEVELOPMENT, 2016, 20 (08) :1540-1545

[4] Direct Preparation of Nitriles from Carboxylic Acids in Continuous Flow [J].

Cantillo, David ;

Kappe, C. Oliver .

JOURNAL OF ORGANIC CHEMISTRY, 2013, 78 (20) :10567-10571

[5] Carbonylative Hiyama coupling of aryl halides with arylsilanes under balloon pressure of CO [J].

Chang, Sheng ;

Jin, Ying ;

Zhang, Xiu Rong ;

Sun, Yong Bing .

TETRAHEDRON LETTERS, 2016, 57 (19) :2017-2020

[6] Mild Palladium-Catalyzed Cyanation of (Hetero)aryl Halides and Triflates in Aqueous Media [J].

Cohen, Daniel T. ;

Buchwald, Stephen L. .

ORGANIC LETTERS, 2015, 17 (02) :202-205

[7] Why excess cyanide can be detrimental to Pd-catalyzed cyanation of haloarenes.: Facile formation and characterization of [Pd(CN)3(H)]2- and [Pd(CN)3(Ph)]2- [J].

Dobbs, Kerwin D. ;

Marshall, William J. ;

Grushin, Vladimir V. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (01) :30-31

[8] Mechanisms of catalyst poisoning in palladium-catalyzed cyanation of haloarenes.: Remarkably facile C-N bond activation in the [(Ph3P)4Pd]/[Bu4N]+ CN- system [J].

Erhardt, Stefan ;

Grushin, Vladimir V. ;

Kilpatrick, Alison H. ;

Macgregor, Stuart A. ;

Marshall, William J. ;

Roe, D. Christopher .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (14) :4828-4845

[9] A practical synthesis of highly functionalized aryl nitriles through cyanation of aryl bromides employing heterogeneous Pd/C: in quest of an industrially viable process [J].

Hatsuda, M ;

Seki, M .

TETRAHEDRON, 2005, 61 (41) :9908-9917

[10]

HU XE, 2005, Patent No. 2005033063

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