Oxidative Cleavage of Enamides with Hypervalent Iodine(III)/TMSN₃ under an Air Atmosphere

Ge Liu, Yan Li*, Jie Sheng, Xi-Sheng Wang*

*Department of Chemistry, University of Science and Technology of China, 96 Jinzhai Road, Hefei, Anhui 230026, P. R. of China, Email: liyan08ustc.edu.cn, xswang77ustc.edu.cn

G. Liu, Y. Li, J. Sheng, X.-S. Wang, Synthesis, 2017, 49, 3968-3974.

DOI: 10.1055/s-0036-1589041 (free Supporting Information)

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Abstract

The combination of hypervalent iodine(III) and TMSN₃ promotes an oxidative cleavage of C-C double bonds of enamides under an air atmosphere. This method exhibits good functional group tolerance, broad substrate scope and mild conditions. The reaction also offers an approach to cyanobenzamides with synthetic potential for the preparation of industrial and pharmaceutical nitrogen- and oxygen-containing molecules.

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Key Words

oxidative cleavage, enamides, imides, hypervalent iodine(III), phenyliodonium diacetate, TMSN₃, air atmosphere

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ID: J66-Y2017