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

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

doi:10.1021/acs.orglett.7b00771

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

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

Pharmaceutical Science

Research output: Contribution to journal › Article › peer-review

33 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 S_RN1 mechanism. This method represents a convenient alternative to the classic Sandmeyer reaction.

Original language	English (US)
Pages (from-to)	2518-2521
Number of pages	4
Journal	Organic Letters
Volume	19
Issue number	10
DOIs	https://doi.org/10.1021/acs.orglett.7b00771
State	Published - May 19 2017

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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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.",

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AU - Leas, Derek A.

AU - Dong, Yuxiang

AU - Vennerstrom, Jonathan L.

AU - Stack, Douglas E.

PY - 2017/5/19

Y1 - 2017/5/19

N2 - 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.

AB - 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.

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

Abstract

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