PhICl2-Mediated Conversion of Enamines into α,N-Dichloroimines and Their Reverse Conversion Mediated by Zinc in Methanol

Linlin Tang; Daisy Zhang-Negrerie; Yunfei Du; Kang Zhao

doi:10.1055/s-0033-1341067

Synthesis, Table of Contents

Synthesis 2014; 46(12): 1621-1629
DOI: 10.1055/s-0033-1341067

paper

PhICl₂-Mediated Conversion of Enamines into α,N-Dichloroimines and Their Reverse Conversion Mediated by Zinc in Methanol

Linlin Tang

^aTianjin Key Laboratory for Modern Drug Delivery & High-Efficiency, School of Pharmaceutical Science and Technology, Tianjin University, Tianjin 300072, P. R. of China

,

Daisy Zhang-Negrerie

^aTianjin Key Laboratory for Modern Drug Delivery & High-Efficiency, School of Pharmaceutical Science and Technology, Tianjin University, Tianjin 300072, P. R. of China

,

Yunfei Du*

^aTianjin Key Laboratory for Modern Drug Delivery & High-Efficiency, School of Pharmaceutical Science and Technology, Tianjin University, Tianjin 300072, P. R. of China

^bCollaborative Innovation Center of Chemical Science and Engineering (Tianjin), Tianjin 300072, P. R. of China Fax: +86(22)27404031 Email: duyunfeier@tju.edu.cn Email: kangzhao@tju.edu.cn

,

Kang Zhao*

^aTianjin Key Laboratory for Modern Drug Delivery & High-Efficiency, School of Pharmaceutical Science and Technology, Tianjin University, Tianjin 300072, P. R. of China

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Abstract

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Abstract

Treatment of enamine compounds with iodobenzene dichloride (PhICl₂) conveniently gives a variety of α,N-dichloroimines in high yields. This approach allows the double insertion of the chloro moiety, which is postulated to take place via the iodobenzene dichloride mediated oxidative α-chlorination of the enamine substrates followed by further N-chlorination of the imine intermediates. Furthermore, the obtained α,N-dichloroimines could be converted reversely into the original enamines under reductive conditions using zinc in methanol.

Key words

enamines - iodobenzene dichloride - α,N-dichloroimines - chlorination - zinc

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Supplementary Material

Supporting Information