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Letters in Organic Chemistry

Author(s): Haixuan Liu and Qiang Sha*

DOI: 10.2174/1570178618666210624115748

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ZnCl2/PhI=O Mediated Selective ortho-Chlorination of Amides

Page: [173 - 180] Pages: 8

  • * (Excluding Mailing and Handling)

Abstract

A new ortho-chlorination system consisting of zinc(II) and hypervalent iodine(III) reagent was developed for ortho-chlorination of amides, and the desired products were obtained in moderate to good yields (38-85%). This highly facile and convenient methodology is tolerant of aromatic amide and alkyl amide with diverse substituted groups. A plausible mechanism has been illustrated, in which carbocation rearrangement and metal salt coordinate facilitated orthochlorination are involved.

Keywords: Zinc, hypervalent iodine, ortho-chlorination, amide, carbocation, selectivity.

Graphical Abstract

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