A Mild and General One-Pot Synthesis of Densely Functionalized Diaryliodonium Salts

Linlin Qin; Bao Hu; Kiel D. Neumann; Ethan J. Linstad; Katelyenn McCauley; Jordan Veness; Jayson J. Kempinger; Stephen G. DiMagno

doi:10.1002/ejoc.201500986

A Mild and General One-Pot Synthesis of Densely Functionalized Diaryliodonium Salts

Linlin Qin, Bao Hu, Kiel D. Neumann, Ethan J. Linstad, Katelyenn McCauley, Jordan Veness, Jayson J. Kempinger, Stephen G. DiMagno

Chemistry

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

43 Scopus citations

Abstract

Diaryliodonium salts are powerful and widely used arylating agents in organic chemistry. Here we report a scalable synthesis of densely functionalized diaryliodonium salts from aryl iodides under mild conditions. This two-step, one-pot process has remarkable functional group tolerance, is compatible with commonly employed acid-labile protective group strategies, avoids heavy metal and transition metal reagents, and provides a direct route to stable precursors to PET imaging agents.

Original language	English (US)
Pages (from-to)	5919-5924
Number of pages	6
Journal	European Journal of Organic Chemistry
Volume	2015
Issue number	27
DOIs	https://doi.org/10.1002/ejoc.201500986
State	Published - Sep 1 2015

Keywords

Aryl iodides
Iodane synthesis
Iodine
Iodonium salts
Oxidation
Synthetic methods

ASJC Scopus subject areas

Physical and Theoretical Chemistry
Organic Chemistry

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10.1002/ejoc.201500986

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abstract = "Diaryliodonium salts are powerful and widely used arylating agents in organic chemistry. Here we report a scalable synthesis of densely functionalized diaryliodonium salts from aryl iodides under mild conditions. This two-step, one-pot process has remarkable functional group tolerance, is compatible with commonly employed acid-labile protective group strategies, avoids heavy metal and transition metal reagents, and provides a direct route to stable precursors to PET imaging agents.",

keywords = "Aryl iodides, Iodane synthesis, Iodine, Iodonium salts, Oxidation, Synthetic methods",

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T1 - A Mild and General One-Pot Synthesis of Densely Functionalized Diaryliodonium Salts

AU - Qin, Linlin

AU - Hu, Bao

AU - Neumann, Kiel D.

AU - Linstad, Ethan J.

AU - McCauley, Katelyenn

AU - Veness, Jordan

AU - Kempinger, Jayson J.

AU - DiMagno, Stephen G.

PY - 2015/9/1

Y1 - 2015/9/1

N2 - Diaryliodonium salts are powerful and widely used arylating agents in organic chemistry. Here we report a scalable synthesis of densely functionalized diaryliodonium salts from aryl iodides under mild conditions. This two-step, one-pot process has remarkable functional group tolerance, is compatible with commonly employed acid-labile protective group strategies, avoids heavy metal and transition metal reagents, and provides a direct route to stable precursors to PET imaging agents.

AB - Diaryliodonium salts are powerful and widely used arylating agents in organic chemistry. Here we report a scalable synthesis of densely functionalized diaryliodonium salts from aryl iodides under mild conditions. This two-step, one-pot process has remarkable functional group tolerance, is compatible with commonly employed acid-labile protective group strategies, avoids heavy metal and transition metal reagents, and provides a direct route to stable precursors to PET imaging agents.

KW - Aryl iodides

KW - Iodane synthesis

KW - Iodine

KW - Iodonium salts

KW - Oxidation

KW - Synthetic methods

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JO - European Journal of Organic Chemistry

JF - European Journal of Organic Chemistry

IS - 27

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A Mild and General One-Pot Synthesis of Densely Functionalized Diaryliodonium Salts

Abstract

Keywords

ASJC Scopus subject areas

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