Copper-Mediated Sequential Cyanation of Aryl C–B and Arene C–H Bonds Using Ammonium Iodide and DMF

J Kim, J Choi, K Shin, S Chang

Index: Kim, Jinho; Choi, Jiho; Shin, Kwangmin; Chang, Sukbok Journal of the American Chemical Society, 2012 , vol. 134, # 5 p. 2528 - 2531

Full Text: HTML

Citation Number: 105

Abstract

The cyanation of aromatic boronic acids, boronate esters, and borate salts was developed under copper-mediated oxidative conditions using ammonium iodide and DMF as the source of nitrogen and carbon atom of the cyano unit, respectively. The procedure was successfully extended to the cyanation of electron-rich benzenes, and regioselective introduction of a cyano group at the arene C–H bonds was also achieved. The ...

~96%

~80%

~78%

~74%

~58%

~61%

~79%

~69%

~53%

~94%

~80%

~74%

~96%

~89%

~87%

~78%

~53%

~90%

~47%

~85%

~69%

~71%

Simple and efficient copper-catalyzed one-pot conversion of ...

[Capdevielle, Patrice; Lavigne, Andre; Maumy, Michel Synthesis, 1989 , # 6 p. 451 - 452]

Application of Polymer??Supported Triphenylphosphine and Mic...

[Srivastava, Rajiv R.; Zych, Andrew J.; Jenkins, David M.; Wang, Hong-Jun; Chen, Zhen-Jia; Fairfax, David J. Synthetic Communications, 2007 , vol. 37, # 3 p. 431 - 438]

Copper-Mediated Transformation of Organosilanes to Nitriles ...

[Wang, Zhen; Chang, Sukbok Organic Letters, 2013 , vol. 15, # 8 p. 1990 - 1993]

Cu2O??Mediated Room Temperature Cyanation of Aryl Boronic Ac...

[Ye, Yong; Wang, Yanhua; Liu, Pengtang; Han, Fushe Chinese Journal of Chemistry, 2013 , vol. 31, # 1 p. 27 - 30]

A General Rhodium??Catalyzed Cyanation of Aryl and Alkenyl B...

[Anbarasan, Pazhamalai; Neumann, Helfried; Beller, Matthias Angewandte Chemie - International Edition, 2011 , vol. 50, # 2 p. 519 - 522]