An alternative to the Sandmeyer approach to aryl iodides

Bao Hu; William H. Miller; Kiel D. Neumann; Ethan J. Linstad; Stephen G. DiMagno

doi:10.1002/chem.201500151

An alternative to the Sandmeyer approach to aryl iodides

Bao Hu, William H. Miller, Kiel D. Neumann, Ethan J. Linstad, Stephen G. DiMagno

Chemistry

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

22 Scopus citations

Abstract

Iodoarenes are important synthons for a wide range of organic transformations. Here we report a general strategy to prepare singly iodinated electron-rich aromatic compounds through the intermediacy of diaryliodonium salts. This process, which incorporates a phase separation that greatly simplifies product purification, is an attractive replacement for the Sandmeyer approach to iodoarenes that are otherwise difficult to access.

Original language	English (US)
Pages (from-to)	6394-6398
Number of pages	5
Journal	Chemistry - A European Journal
Volume	21
Issue number	17
DOIs	https://doi.org/10.1002/chem.201500151
State	Published - Apr 20 2015

Keywords

Sandmeyer reaction
aryl iodides
diaryliodonium salt
electrophilic substitution
regioselectivity

ASJC Scopus subject areas

Catalysis
Organic Chemistry

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10.1002/chem.201500151

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title = "An alternative to the Sandmeyer approach to aryl iodides",

abstract = "Iodoarenes are important synthons for a wide range of organic transformations. Here we report a general strategy to prepare singly iodinated electron-rich aromatic compounds through the intermediacy of diaryliodonium salts. This process, which incorporates a phase separation that greatly simplifies product purification, is an attractive replacement for the Sandmeyer approach to iodoarenes that are otherwise difficult to access.",

keywords = "Sandmeyer reaction, aryl iodides, diaryliodonium salt, electrophilic substitution, regioselectivity",

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T1 - An alternative to the Sandmeyer approach to aryl iodides

AU - Hu, Bao

AU - Miller, William H.

AU - Neumann, Kiel D.

AU - Linstad, Ethan J.

AU - DiMagno, Stephen G.

PY - 2015/4/20

Y1 - 2015/4/20

N2 - Iodoarenes are important synthons for a wide range of organic transformations. Here we report a general strategy to prepare singly iodinated electron-rich aromatic compounds through the intermediacy of diaryliodonium salts. This process, which incorporates a phase separation that greatly simplifies product purification, is an attractive replacement for the Sandmeyer approach to iodoarenes that are otherwise difficult to access.

AB - Iodoarenes are important synthons for a wide range of organic transformations. Here we report a general strategy to prepare singly iodinated electron-rich aromatic compounds through the intermediacy of diaryliodonium salts. This process, which incorporates a phase separation that greatly simplifies product purification, is an attractive replacement for the Sandmeyer approach to iodoarenes that are otherwise difficult to access.

KW - Sandmeyer reaction

KW - aryl iodides

KW - diaryliodonium salt

KW - electrophilic substitution

KW - regioselectivity

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ER -

An alternative to the Sandmeyer approach to aryl iodides

Abstract

Keywords

ASJC Scopus subject areas

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