Citation: Ai-E Wang, Zong Chang, Yong-Peng Liu, Pei-Qiang Huang. Mild N-deacylation of secondary amides by alkylation with organocerium reagents[J]. Chinese Chemical Letters, ;2015, 26(9): 1055-1058. doi: 10.1016/j.cclet.2015.05.033 shu

Mild N-deacylation of secondary amides by alkylation with organocerium reagents

1.
Department of Chemistry, College of Chemistry and Chemical Engineering, and Fujian Provincial Key Laboratory of Chemical Biology, Xiamen University, Xiamen 361005, China

Corresponding author: Ai-E Wang, Pei-Qiang Huang,
Received Date: 3 April 2015
Available Online: 11 May 2015
Fund Project: The authors are grateful for financial support from the National Natural Science Foundation of China (No. 21332007) (No. 21332007) and the Natural Science Foundation of Fujian Province of China (No. 2014J01062). (PCSIRT)

Secondary amides are a class of highly stable compounds serving as versatile starting materials, intermediates and directing groups (amido groups) in organic synthesis. The direct deacylation of secondary amides to release amines is an important transformation in organic synthesis. Here, we report a protocol for the deacylation of secondary amides and isolation of amines. The method is based on the activation of amides with Tf₂O, followed by addition of organocerium reagents, and acidic work-up. The reaction proceeded under mild conditions and afforded the corresponding amines, isolated as their hydrochloride salts, in good yields. In combination with the C-H activation functionalization methodology, the method is applicable to the functionalization of aniline as well as conversion of carboxylic derivatives to functionalized ketones.
- N-Deacylation,
- Amides,
- Amines,
- Organocerium
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