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- Title
Diaryl Sulfoxides from Aryl Benzyl Sulfoxides: A Single Palladium-Catalyzed Triple Relay Process.
- Authors
Jia, Tiezheng; Bellomo, Ana; Montel, Sonia; Zhang, Mengnan; EL Baina, Kawtar; Zheng, Bing; Walsh, Patrick J.
- Abstract
A novel approach to produce diaryl sulfoxides from aryl benzyl sulfoxides is reported. Optimization of the reaction conditions was performed using high-throughput experimentation techniques. The [Pd(dba)2]/NiXantPhos catalyst system successfully promotes a triple relay process involving sulfoxide α-arylation, CS bond cleavage, and CS bond formation. The byproduct benzophenone is formed by an additional palladium-catalyzed process. It is noteworthy that palladium-catalyzed benzylative CS bond cleavage of sulfoxides is unprecedented. A wide range of aryl benzyl sulfoxides, as well as alkyl benzyl sulfoxides with various (hetero)aryl bromides were employed in the triple relay process in good to excellent yields (85-99 %). Moreover, aryl methyl sulfoxides, dibenzyl sulfoxides, and dimethylsulfoxide could be utilized to generate diaryl sulfoxides involving multiple catalytic cycles by a single catalyst.
- Subjects
SULFOXIDE derivatives; PALLADIUM catalysts; CHEMICAL bonds; DIMETHYL sulfoxide; SCISSION (Chemistry)
- Publication
Angewandte Chemie International Edition, 2014, Vol 53, Issue 1, p260
- ISSN
1433-7851
- Publication type
Article
- DOI
10.1002/anie.201307172