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Organobase-Catalyzed Umpolung of Amides: The Generation and Transfer of Carbamoyl Anion.

Qi LiWang ZhangChen ZhuHong PanKang-Yue ShiYicheng ZhangMan-Yi HanChoon Hong Tan
Published in: The Journal of organic chemistry (2023)
A novel organobase-catalyzed umpolung reaction of amides was disclosed. This method provides an efficient method to generate and transfer carbamoyl anions. In this transformation, some of the inherent disadvantages of carbamoyl metal were avoided. The mechanistic analysis revealed that the reaction proceeds through polarity inversion of amide, and various carbamoyl anions were applied in the reaction. Moreover, a wide range of substrates was achieved with moderate to excellent yield.
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