DBU Catalysis of N,N'-Carbonyldiimidazole-Mediated Amidations
Claude Larrive-Aboussafy, Brian P. Jones, Kristin E. Price, Mark A. Hardink, Robert W. McLaughlin, Brett M. Lillie, Joel M. Hawkins and Rajappa Vaidyanathan*
*Development Science and Technology, Pfizer Inc., Eastern Point Road, Groton, Connecticut 06340, Email: rajappa.vaidyanathanpfizer.com
C. Larrive-Aboussafy, B. P. Jones, K. E. Price, M. A. Hardink, R. W. McLaughlin, B. M. Lillie, J. M. Hawkins, R. Vaidyanathan, Org. Lett., 2010, 12, 324-327.
DOI: 10.1021/ol9026599 (free Supporting Information)
1,8-Diazabicyclo[5.4.0]undec-7-ene (DBU) catalyzes the amidation of acyl imidazoles. The rate acceleration is especially evident with traditionally unreactive, electron-deficient anilines. DBU offers safety and cost advantages over more commonly employed catalysts such as 1-hydroxybenzotriazole (HOBt).
see article for more examples