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

Psychiatry

University of Nebraska-Lincoln

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

48 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
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

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10.1002/ejoc.201500986

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title = "A Mild and General One-Pot Synthesis of Densely Functionalized Diaryliodonium Salts",

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",

author = "Linlin Qin and Bao Hu and Neumann, \{Kiel D.\} and Linstad, \{Ethan J.\} and Katelyenn McCauley and Jordan Veness and Kempinger, \{Jayson J.\} and DiMagno, \{Stephen G.\}",

note = "Publisher Copyright: Copyright {\textcopyright} 2015 WILEY-VCH Verlag GmbH \& Co. KGaA, Weinheim.",

year = "2015",

month = sep,

day = "1",

doi = "10.1002/ejoc.201500986",

language = "English",

volume = "2015",

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journal = "European Journal of Organic Chemistry",

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TY - JOUR

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

UR - https://www.scopus.com/pages/publications/84941565159

U2 - 10.1002/ejoc.201500986

DO - 10.1002/ejoc.201500986

M3 - Article

AN - SCOPUS:84941565159

SN - 1434-193X

VL - 2015

SP - 5919

EP - 5924

JO - European Journal of Organic Chemistry

JF - European Journal of Organic Chemistry

IS - 27

ER -

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

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Keywords

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