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

Derek A. Leas, Yuxiang Dong, Jonathan L. Vennerstrom, Douglas E. Stack

Research output: Contribution to journalArticle

19 Scopus citations

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.

Original languageEnglish (US)
Pages (from-to)2518-2521
Number of pages4
JournalOrganic Letters
Volume19
Issue number10
DOIs
StatePublished - May 19 2017

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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