Issue 6, 2000
From the journal:

Journal of the Chemical Society, Perkin Transactions 1

Palladium(II)-mediated 11C-carbonylative coupling of diaryliodonium salts with organostannanes—a new, mild and rapid synthesis of aryl [11C]ketones

Mohammed H. Al-Qahtanib  and  Victor W. Pike*a  

* Corresponding authors

a Chemistry and Engineering Group, MRC Cyclotron Unit, Imperial College School of Medicine, Hammersmith Hospital, Ducane Road, London, UK
E-mail: victor.pike@csc.mrc.ac.uk

b Department of Chemistry, School of Physics and Chemistry, University of Surrey, Guildford, UK

Abstract

Palladium(II)-mediated [11C]carbonylative coupling of diaryliodonium salts with aryltributylstannanes for 1 min in DME–water (4∶1 v/v) at RT gives a new mild and rapid route to aryl [11C]ketones. Substituted aryltributylstannanes couple with diphenyliodonium bromide to give substituted [11C]benzophenones in generally very high radiochemical yield (>98%, decay-corrected), while diphenyliodonium tosylates, bearing one or two substituents in one ring, couple with phenyltributylstannane to give a mixture of substituted (30–43%) and unsubstituted [11C]benzophenone (47–66%). These reactions are highly attractive for introducing cyclotron-produced carbon-11 (t1/2 = 20.4 min) into prospective radiotracers for application in medical imaging with positron emission tomography.

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Article information

DOI
https://doi.org/10.1039/A907803G
Article type
Paper
Submitted
28 Sep 1999
Accepted
28 Jan 2000
First published
22 Feb 2000

J. Chem. Soc., Perkin Trans. 1, 2000, 1033-1036

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Palladium(II)-mediated 11C-carbonylative coupling of diaryliodonium salts with organostannanes—a new, mild and rapid synthesis of aryl [11C]ketones

M. H. Al-Qahtani and V. W. Pike, J. Chem. Soc., Perkin Trans. 1, 2000, 1033 DOI: 10.1039/A907803G

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