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Organocatalytic Direct N-Acylation of Amides with Aldehydes under Oxidative Conditions

Chenguang Zheng, Xiang Liu and Cheng Ma*

*Department of Chemistry, Zhejiang University, 20 Yugu Road, Hangzhou 310027, China, Email:

C. Zheng, Y. Liu, C. Ma, J. Org. Chem., 2017, 82, 6940-6945.

DOI: 10.1021/acs.joc.7b00457

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The direct oxidative N-acylation reaction of primary amides with aryl/α,β-unsaturated aldehydes was achieved in the presence of an azolium salt and an inorganic base using 3,3′,5,5′-tetra-tert-butyldiphenoquinone as the oxidant. The reaction provides an efficient approach for the synthesis of N-sulfonylcarboxamides, N-sulfinylcarboxamides, and dicarboxyimides in good yield.

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Key Words

sulfonamides, 3,3′,5,5′-tetra-tert-butyldiphenoquinone, organocatalysis

ID: J42-Y2017