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

ABSTRACT: 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.

SUBMITTER: Leas DA

PROVIDER: S-EPMC5572204 | biostudies-literature | 2017 May

REPOSITORIES: biostudies-literature

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

Leas Derek A DA Dong Yuxiang Y Vennerstrom Jonathan L JL Stack Douglas E DE

Organic letters 20170508 10

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 represen ...[more]

PMID: 28481557

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