April 1st (Thu) Graduate Seminar / Prof. Seonwoo Lee

Development of Synthetic Methods using

C-N Bond Activation

The amide functionality is one of the key structural motifs found in biological compounds such as peptides, proteins, and alkaloids. It is also widely used to prepare agrochemicals, pharmaceuticals, polymers, and materials. Therefore, a number of synthetic routes to amides have been reported. We developed the nickel-catalyzed transamidation of unactivated secondary amides and the Claisen condensation reaction between two different amides. It was found that nickel activated C-N bond of amides. In addition, the transamidation of primary amides at room temperature was developed by our group. 1

We also reported the amide coupling reaction with carbon nucleophiles such as carbonyl compounds and aryl siloxanes to give the corresponding acylated products. 2

  In this seminar, the details about our recent findings of the C-N bond activations for the synthesis of different type of amides and ketones will be presented.

References

1. (a) S. Yu, T. Shin, M. Zhang, Y. Xia, H. Kim, S. Lee, Org. Lett. 2018 , 20 , 7563. (b) J. Chen, Y. Xia, S. Lee, Org. Lett. 2020 , 22 , 3504. (c) D. Yang, T. Shin, H. Kim, S. Lee. Org. Biomol. Chem . 2020 , 18 , 6053. (d) M. A. Idris, S. Lee, Org. Chem. Front. 2020 , 7 , 2737.

(a) J. Chen, M. Xu, S. Yu, Y. Xia, S. Lee, Org. Lett. 2020 , 22 , 2287. (b) J. Chen, Y. Xia, S. Lee, Org. Chem. Front. 2020 , 7 , 2931. (c) M. 2. A. Idris, S. Lee, Org. Lett. 2020 . 22 , 9190.