Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 76, Issue 12, Pages 4987-4994Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo200666z
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Funding
- National Basic Research Program of China [2011CB936003]
- NSFC [20872126, 2107216]
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Palladium-catalyzed C-H activation reactions directed by a removable 2-pyridylsulfinyl group were developed. Aromatic olefination products were formed in good yields on treatment of 2-(phenylsulfinyl)pyridines with alkenes in the presence of a Pd catalyst. The reaction tolerates a wide range of substituted alkenes, including various acrylates and styrenes. The controlled experiments indicated that the 2-pyridyl moiety, rather than the sulfinyl, played the role of ligand. The final reductive desulfonylation affords the stilbenes, sulfides, and disulfides with different reductive conditions, respectively. More importantly, this transformation could also be applied in arylation through dual C-H activation.
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