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Aminochlorination in Water: First Brønsted Acid-Promoted Synthesis of Vicinal Chloramines

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Xue-Liang Wu and Guan-Wu Wang*

Hefei National Laboratory for Physical Sciences at Microscale, Joint Laboratory of Green Synthetic Chemistry, and Department of Chemistry, University of Science and Technology of China, Hefei, Anhui 230026, People's Republic of China gwang@ustc.edu.cn

J. Org. Chem., 2007, 72 (24), pp 9398–9401

DOI: 10.1021/jo701957t

Publication Date (Web): October 31, 2007

Section:

Benzene, Its Derivatives, and Condensed Benzenoid Compounds

Abstract

A practical and scaleable route for the regio- and diastereoselective synthesis of vicinal chloramines from electron-deficient olefins and Chloramine-T promoted by Brønsted acids in water has been realized for the first time. This novel protocol is efficient, mild, ecofriendly, and broadly applicable for the aminochlorination of various electron-deficient olefins including α,β-unsaturated ketones, cinnamate, and cinnamide. Water represents as a privileged solvent for the aminochlorination reaction in our system.

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Published In Issue November 23, 2007
Received September 5, 2007

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Aminochlorination in Water: First Brønsted Acid-Promoted Synthesis of Vicinal Chloramines