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J Am Chem Soc. 2013 Mar 13;135(10):3740-3. doi: 10.1021/ja4009776. Epub 2013 Feb 27.

Palladium-catalyzed direct arylation of methyl sulfoxides with aryl halides.

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1
Roy and Diana Vagelos Laboratories, Penn/Merck Laboratory for High-Throughput Experimentation, Department of Chemistry, University of Pennsylvania, 231 South 34th Street, Philadelphia, Pennsylvania 19104-6323, USA.

Abstract

The palladium-catalyzed α-arylation of unactivated sulfoxides has been developed. The weakly acidic α-protons of sulfoxides are reversibly deprotonated by LiOtBu, and a palladium phosphine complex facilitates the arylation. A variety of aryl methyl sulfoxides were coupled with aryl bromides. More challenging coupling partners, such as alkyl methyl sulfoxides (including dimethyl sulfoxide) and aryl chlorides proved to be suitable under the optimized conditions. This method was utilized to synthesize bioactive benzyl sulfoxide intermediates.

PMID:
23419158
DOI:
10.1021/ja4009776
[Indexed for MEDLINE]
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