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Synlett 2005(20): 3154-3156  
DOI: 10.1055/s-2005-922751
LETTER
© Georg Thieme Verlag Stuttgart · New York

Carboxylation of Alkyl Iodides with [11C] and (13C)Carbon Monoxide: Using Sulfoxides as Oxygen Nucleophiles

Oleksiy Itsenkoa, Tor Kihlbergb, Bengt Långström*a,b
a Department of Organic Chemistry, Institute of Chemistry, Uppsala University, Box 599, 751 21 Uppsala, Sweden
b Uppsala Imanet AB, Box 967, 751 09 Uppsala, Sweden
Fax: +46(18)666819; e-Mail: bengt.langstrom@uppsala.imanet.se;
Further Information

Publication History

Received 13 October 2005
Publication Date:
28 November 2005 (online)

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Abstract

11C-Labeled carboxylic acids were prepared from alkyl iodides and [11C]carbon monoxide by irradiation by UV light in anhydrous DMSO solutions in the presence of triethylamine. Sulf­oxides other than DMSO can be used and may be used in stoichiometric amounts using inert solvents.

Key words

sulfoxides - radical reactions - carbonylations - carboxylic acid - photochemistry

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11

Typically, [11C]carbon monoxide is available in submicromolar amounts, whereas other reactants may be used on a submillimolar scale.

14

The yield was calculated from (13C)carbon monoxide, the reaction conditions were not optimized.