A Mild Method for Regioselective Labeling of Aromatics with Radioactive Iodine

Mads Holger Rønnest; Felix Nissen; Palle Jacob Pedersen; Thomas Ostenfeld Larsen; Walter Mier; Mads Hartvig Clausen

doi:10.1002/ejoc.201300419

A Mild Method for Regioselective Labeling of Aromatics with Radioactive Iodine

Mads Holger Rønnest
, Felix Nissen
, Palle Jacob Pedersen
, Thomas Ostenfeld Larsen
, Walter Mier
, Mads Hartvig Clausen

University Hospital Heidelberg

Research output: Contribution to journal › Journal article › Research › peer-review

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Abstract

A novel technique to label ortho‐, meta‐, and para‐trimethylsilyl‐substituted aryl substituents with radioactive iodide is described. The method takes advantage of the ipso‐directing and activating properties of trimethylsilyl substituents on the arenes. The method was demonstrated on a griseofulvin analogue with promising anticancer properties and on lidocaine, a widely used local anesthetic drug. Treatment of a trimethylsilyl precursor with Tl(OCOCF3)3 followed by Na125I consistently afforded radioactive purities over 95 % in all cases.

Original language	English
Journal	European Journal of Organic Chemistry
Volume	2013
Issue number	19
Pages (from-to)	3970-3973
ISSN	1434-193X
DOIs	https://doi.org/10.1002/ejoc.201300419
Publication status	Published - 2013

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title = "A Mild Method for Regioselective Labeling of Aromatics with Radioactive Iodine",

abstract = "A novel technique to label ortho‐, meta‐, and para‐trimethylsilyl‐substituted aryl substituents with radioactive iodide is described. The method takes advantage of the ipso‐directing and activating properties of trimethylsilyl substituents on the arenes. The method was demonstrated on a griseofulvin analogue with promising anticancer properties and on lidocaine, a widely used local anesthetic drug. Treatment of a trimethylsilyl precursor with Tl(OCOCF3)3 followed by Na125I consistently afforded radioactive purities over 95 \% in all cases.",

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T1 - A Mild Method for Regioselective Labeling of Aromatics with Radioactive Iodine

AU - Rønnest, Mads Holger

AU - Nissen, Felix

AU - Pedersen, Palle Jacob

AU - Larsen, Thomas Ostenfeld

AU - Mier, Walter

AU - Clausen, Mads Hartvig

PY - 2013

Y1 - 2013

N2 - A novel technique to label ortho‐, meta‐, and para‐trimethylsilyl‐substituted aryl substituents with radioactive iodide is described. The method takes advantage of the ipso‐directing and activating properties of trimethylsilyl substituents on the arenes. The method was demonstrated on a griseofulvin analogue with promising anticancer properties and on lidocaine, a widely used local anesthetic drug. Treatment of a trimethylsilyl precursor with Tl(OCOCF3)3 followed by Na125I consistently afforded radioactive purities over 95 % in all cases.

AB - A novel technique to label ortho‐, meta‐, and para‐trimethylsilyl‐substituted aryl substituents with radioactive iodide is described. The method takes advantage of the ipso‐directing and activating properties of trimethylsilyl substituents on the arenes. The method was demonstrated on a griseofulvin analogue with promising anticancer properties and on lidocaine, a widely used local anesthetic drug. Treatment of a trimethylsilyl precursor with Tl(OCOCF3)3 followed by Na125I consistently afforded radioactive purities over 95 % in all cases.

U2 - 10.1002/ejoc.201300419

DO - 10.1002/ejoc.201300419

M3 - Journal article

SN - 1434-193X

VL - 2013

SP - 3970

EP - 3973

JO - European Journal of Organic Chemistry

JF - European Journal of Organic Chemistry

IS - 19

ER -

A Mild Method for Regioselective Labeling of Aromatics with Radioactive Iodine

Abstract

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