Synthesis 2017; 49(17): 3968-3974
DOI: 10.1055/s-0036-1589041
paper
© Georg Thieme Verlag Stuttgart · New York

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

Ge Liu
Hefei National Laboratory for Physical Sciences at the Microscale and Department of Chemistry, University of Science and Technology of China, 96 Jinzhai Road, Hefei, Anhui 230026, P. R. of China   Email: [email protected]   Email: [email protected]
,
Yan Li*
Hefei National Laboratory for Physical Sciences at the Microscale and Department of Chemistry, University of Science and Technology of China, 96 Jinzhai Road, Hefei, Anhui 230026, P. R. of China   Email: [email protected]   Email: [email protected]
,
Jie Sheng
Hefei National Laboratory for Physical Sciences at the Microscale and Department of Chemistry, University of Science and Technology of China, 96 Jinzhai Road, Hefei, Anhui 230026, P. R. of China   Email: [email protected]   Email: [email protected]
,
Hefei National Laboratory for Physical Sciences at the Microscale and Department of Chemistry, University of Science and Technology of China, 96 Jinzhai Road, Hefei, Anhui 230026, P. R. of China   Email: [email protected]   Email: [email protected]
› Author Affiliations
We gratefully acknowledge the National Science Foundation of China (21602213, 21522208, 21372209) for financial support.
Further Information

Publication History

Received: 29 March 2017

Accepted after revision: 05 May 2017

Publication Date:
20 June 2017 (online)


Abstract

An oxidative cleavage of C–C double bonds of enamides promoted by hypervalent iodine(III)/TMSN3 under an air atmosphere is developed. This reaction provides a new approach to construct various cyanobenzamides, which offers further synthetic potential for the preparation of industrial and pharmaceutical nitrogen- and oxygen-containing molecules, and exhibits good functional group tolerance, broad substrate scope and mild conditions.

Supporting Information

 
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