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.

DOI: 10.1021/acs.orglett.7b00429

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Abstract

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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Metal-Free Transamidation of Secondary Amides by N-C Cleavage

Md. M. Rahman, G. Li, M. Szostak, J. Org. Chem., 2019, 84, 12091-12100.

Thioesterification and Selenoesterification of Amides via Selective N-C Cleavage at Room Temperature: N-C(O) to S/Se-C(O) Interconversion

Md. M. Rahman, G. Li, M. Szostak, Synthesis, 2020, 52, 1060-1066.

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Key Words

amides, transamidation

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ID: J54-Y2017