A General and Convenient Catalytic Synthesis of Nitriles from Amides and Silanes

作者: Shaolin Zhou , Kathrin Junge , Daniele Addis , Shoubhik Das , Matthias Beller

DOI: 10.1021/OL900716Q

关键词:

摘要: A new and convenient protocol for the catalytic dehydration of aromatic aliphatic amides using silanes in presence amounts fluoride is presented. The synthesis nitriles proceeds with high selectivity under mild conditions. Notably, a wide substrate range converted good to excellent yields.

参考文章(47)
James Lindley, Tetrahedron report number 163 Tetrahedron. ,vol. 40, pp. 1433- 1456 ,(1984) , 10.1016/S0040-4020(01)91791-0
Gwynn P. Ellis, Trevor M. Romney-Alexander, Cyanation of aromatic halides Chemical Reviews. ,vol. 87, pp. 779- 794 ,(1987) , 10.1021/CR00080A006
Xin Wang, Ben Zhi, Jean Baum, Ying Chen, Richard Crockett, Liang Huang, Shawn Eisenberg, John Ng, Robert Larsen, Mike Martinelli, Paul Reider, A practical synthesis of 2-((1H-pyrrolo[2,3-b]pyridine-4-yl)methylamino)-5- fluoronicotinic acid. Journal of Organic Chemistry. ,vol. 71, pp. 4021- 4023 ,(2006) , 10.1021/JO0602571
Stephan Enthaler, Kathrin Junge, Matthias Beller, Eisenkatalyse – ein nachhaltiges Prinzip mit Perspektive? Angewandte Chemie. ,vol. 120, pp. 3363- 3367 ,(2008) , 10.1002/ANGE.200800012
Mark Sundermeier, Alexander Zapf, Matthias Beller, Jürgen Sans, A new palladium catalyst system for the cyanation of aryl chlorides Tetrahedron Letters. ,vol. 42, pp. 6707- 6710 ,(2001) , 10.1016/S0040-4039(01)01390-9
Henri-Jean Cristau, Armelle Ouali, Jean-Francis Spindler, Marc Taillefer, Mild and Efficient Copper-Catalyzed Cyanation of Aryl Iodides and Bromides Chemistry: A European Journal. ,vol. 11, pp. 2483- 2492 ,(2005) , 10.1002/CHEM.200400979
Mark Sundermeier, Alexander Zapf, Matthias Beller, Palladium‐Catalyzed Cyanation of Aryl Halides: Recent Developments and Perspectives European Journal of Inorganic Chemistry. ,vol. 2003, pp. 3513- 3526 ,(2003) , 10.1002/EJIC.200300162
W. Lehnert, Nitrile aus primären carbonsäureamiden mit TiCl4/base bei O °C. Tetrahedron Letters. ,vol. 12, pp. 1501- 1502 ,(1971) , 10.1016/S0040-4039(01)96994-1