Tf₂O/TTBP (2,4,6-Tri-tert-butylpyrimidine): An Alternative Amide Activation System for the Direct Transformations of Both Tertiary and Secondary Amides

Qian He, Jian-Liang Ye, Fang-Fang Xu, Hui Geng, Ting-Ting Chen, Hang Chen and Pei-Qiang Huang*

*Department of Chemistry, College of Chemistry and Chemical Engineering, Xiamen University, Xiamen, Fujian 361005, P. R. China, Email: pqhuangxmu.edu.cn

Q. He, J.-L. Ye, F.-F. Xu, H. Geng, T.-T. Chen, H. Chen, P.-Q. Huang, J. Org. Chem., 2021, 86, 16300-16314.

DOI: 10.1021/acs.joc.1c01572

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Abstract

Tf₂O/TTBP can serve as an alternative amide activation system for direct conversions of secondary and tertiary amides. Reductive (di)alkylations, condensations, and Bischler-Napieralski reactions with TTBP deliver higher or similar yields compared with pyridine derivatives 2,6-di-tert-butyl-4-methylpyridine (DTBMP) and 2-fluoropyridine (2-F-Pyr.). TTBP can easily be recovered and reused.

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Key Words

alkylation, sodium borohydride

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ID: J42-Y2021