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I2/Aqueous TBHP-Catalyzed Coupling of Amides with Methylarenes/Aldehydes/Alcohols: Metal-Free Synthesis of Imides

Hariprasad Aruri, Umed Singh, Sanjay Kumar, Manoj Kushwaha, Ajai Prakash Gupta, Ram A. Vishwakarma and Parvinder Pal Singh*

*Medicinal Chemistry Division and §Quality Control and Quality Assurance, CSIR-Indian Institute of Integrative Medicine, Canal Road, Jammu 180001, India, Email:

H. Aruri, U. Singh, S. Kumar, M. Kushwaha, A. P. Gupta, R. A. Vishwakarma, P. P. Singh, Org. Lett., 2016, 18, 3638-3641.

DOI: 10.1021/acs.orglett.6b01684 (free Supporting Information)

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A direct coupling of NH-amides with methylarenes under iodine/aqueous TBHP conditions enables a metal-free synthesis of imides. The optimized conditions worked also very well with benzaldehydes and benzyl alcohol and furnished the corresponding imides in good to excellent yields.

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Key Words

imides (C-N coupling, oxidation), TBHP

ID: J54-Y2016