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

Qi Li, Wang Zhang, Chen Zhu, Hong Pan, Kang-Yue Shi, Yicheng Zhang, Man-Yi Han, Choon-Hong Tan

The Journal of organic chemistry 2023 Jan 20

filter terms:

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.

Citation

Qi Li, Wang Zhang, Chen Zhu, Hong Pan, Kang-Yue Shi, Yicheng Zhang, Man-Yi Han, Choon-Hong Tan. Organobase-Catalyzed Umpolung of Amides: The Generation and Transfer of Carbamoyl Anion. The Journal of organic chemistry. 2023 Jan 20;88(2):1245-1255