Copper-catalyzed aerobic oxidative synthesis of aryl nitriles from benzylic alcohols and aqueous ammonia

作者: Chuanzhou Tao , Feng Liu , Youmin Zhu , Weiwei Liu , Zhiling Cao

DOI: 10.1039/C3OB00002H

关键词:

摘要: Copper-catalyzed direct conversion of benzylic alcohols to aryl nitriles was realized using NH3(aq.) as the nitrogen source, O2 oxidant and TEMPO co-catalyst. Furthermore, copper-catalyzed one-pot synthesis primary amides from also achieved.

参考文章(44)
Gen Zhang, Yunxia Ma, Shoulei Wang, Yaohu Zhang, Rui Wang, Enantioselective Metal/Organo-Catalyzed Aerobic Oxidative sp3C–H Olefination of Tertiary Amines Using Molecular Oxygen as the Sole Oxidant Journal of the American Chemical Society. ,vol. 134, pp. 12334- 12337 ,(2012) , 10.1021/JA303333K
Guoying Zhang, Xinyi Ren, Jianbin Chen, Maolin Hu, Jiang Cheng, Copper-Mediated Cyanation of Aryl Halide with the Combined Cyanide Source Organic Letters. ,vol. 13, pp. 5004- 5007 ,(2011) , 10.1021/OL201713B
Shengtao Ding, Ning Jiao, Direct Transformation of N,N-Dimethylformamide to −CN: Pd-Catalyzed Cyanation of Heteroarenes via C–H Functionalization Journal of the American Chemical Society. ,vol. 133, pp. 12374- 12377 ,(2011) , 10.1021/JA204063Z
Vladimir V Grushin, Howard Alper, None, Transformations of Chloroarenes, Catalyzed by Transition-Metal Complexes Chemical Reviews. ,vol. 94, pp. 1047- 1062 ,(1994) , 10.1021/CR00028A008
Jinho Kim, Sukbok Chang, A new combined source of "CN" from N,N-dimethylformamide and ammonia in the palladium-catalyzed cyanation of aryl C-H bonds. Journal of the American Chemical Society. ,vol. 132, pp. 10272- 10274 ,(2010) , 10.1021/JA104917T
Gwynn P. Ellis, Trevor M. Romney-Alexander, Cyanation of aromatic halides Chemical Reviews. ,vol. 87, pp. 779- 794 ,(1987) , 10.1021/CR00080A006
Kazuya Yamaguchi, Hiroaki Kobayashi, Takamichi Oishi, Noritaka Mizuno, Heterogeneously Catalyzed Synthesis of Primary Amides Directly from Primary Alcohols and Aqueous Ammonia Angewandte Chemie. ,vol. 51, pp. 544- 547 ,(2012) , 10.1002/ANIE.201107110
Nathan A. Owston, Alexandra J. Parker, Jonathan M. J. Williams, Highly efficient ruthenium-catalyzed oxime to amide rearrangement. Organic Letters. ,vol. 9, pp. 3599- 3601 ,(2007) , 10.1021/OL701445N