Direct Synthesis of α-Amino Nitriles from Sulfonamides via Base-Mediated C-H Cyanation
Shasha Shi, Xianyu Yang, Man Tang, Jiefeng Hu* and Teck-Peng Loh*
*Institute of Advanced Synthesis, School of Chemistry and Molecular Engineering, Nanjing Tech University, Nanjing 211816, China,
Email: iasjfhu
njtech.edu.cn, teckpengntu.edu.sg
S. Shi, X. Yang, M. Tang, J. Hu, T.-P. Loh, Org. Lett., 2021, 23, 4018-4022.
DOI: 10.1021/acs.orglett.1c01232
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Abstract
A transition-metal-free α-cyanation of easy accessible N-fluorotosylsulfonamides provides α-amino nitriles through elimination of HF. More than 50 substrate examples, including difficult-to-access all-alkyl α-tertiary scaffolds, prove a wide functional group tolerance. The method also offers gram-scalability and late-stage modification of natural compounds.
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late-stage functionalizations
proposed reaction pathway
Key Words
ID: J54-Y2021
