Metal-Free Transamidation of Secondary Amides via Selective N-C Cleavage under Mild Conditions
Yongmei Liu, Shicheng Shi, Marcel Achtenhagen, Ruzhang Liu and Michal Szostak*
*Department of Chemistry, Rutgers University, 73 Warren Street, Newark, New Jersey 07102, United States, Email: michal.szostakrutgers.edu
Y. Liu, S. Shi, M. Achtenhagen, R. Liu, M. Szostak, Org. Lett., 2017, 19, 1614-1617.
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Nonplanar, electronically destabilized amides are powerful intermediates in organic synthesis. A highly selective method for transamidation of common secondary amides under mild, metal-free conditions relies on transient N-selective functionalization to weaken amidic resonance. This procedure accomplishes challenging transamidation of secondary amides under mild conditions.
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Md. M. Rahman, G. Li, M. Szostak, J. Org. Chem., 2019, 84, 12091-12100.
Md. M. Rahman, G. Li, M. Szostak, Synthesis, 2020, 52, 1060-1066.