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35.1.5.1.12.2.2 Transition-Metal-Catalyzed Aminochlorination of Alkenes

DOI: 10.1055/sos-SD-135-00173

Wirth, T.; Singh, F. V.Science of Synthesis Knowledge Updates, (20171417.

Various catalytic approaches using transition-metal salts for the aminochlorination of alkenes have been reported.[‌42‌] In 2006, Li and co-workers developed an iron-catalyzed aminochlorination of (arylmethylene)cyclopropanes 33 using N,N-dichloro-4-toluenesulfon­amide (34) as source of both chlorine and nitrogen (Scheme 18). Reactions are carried out in acetonitrile at room temperature and reaction products 35 are isolated in good yields.[‌43‌] Other transition-metal salts were investigated as catalysts, but iron(III) chloride was found to be the most efficient for these aminochlorinations. The same approach has been successfully applied for the aminochlorination of (arylvinylidene)cyclopropanes.[‌43‌]

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References


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