4 years ago

One-Pot, Metal-Free Conversion of Anilines to Aryl Bromides and Iodides

One-Pot, Metal-Free Conversion of Anilines to Aryl Bromides and Iodides
Jonathan L. Vennerstrom, Yuxiang Dong, Douglas E. Stack, Derek A. Leas
A metal-free synthesis of aryl bromides and iodides from anilines via halogen abstraction from bromotrichloromethane and diiodomethane is described. This one-pot reaction affords aryl halides from the corresponding anilines in moderate to excellent yields without isolation of diazonium salts. The transformation has short reaction times, a simple workup, and insensitivity to moisture and air and avoids excess halogenation. DFT calculations support a SRN1 mechanism. This method represents a convenient alternative to the classic Sandmeyer reaction.

Publisher URL: http://dx.doi.org/10.1021/acs.orglett.7b00771

DOI: 10.1021/acs.orglett.7b00771

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