Diaryl Sulfoxides from Aryl Benzyl Sulfoxides: A Single Palladium‐Catalyzed Triple Relay Process |
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| Authors: | Tiezheng Jia Dr Ana Bellomo Dr Sonia Montel Mengnan Zhang Kawtar EL?Baina Bing Zheng Prof Patrick J Walsh |
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| Institution: | Roy and Diana Vagelos Laboratories, Penn/Merck Laboratory for High‐Throughput Experimentation, Department of Chemistry, University of Pennsylvania, 231 S. 34th St. Philadelphia, PA 19104‐6323 (USA) http://titanium.chem.upenn.edu/walsh/ |
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| 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, C? S bond cleavage, and C? S bond formation. The byproduct benzophenone is formed by an additional palladium‐catalyzed process. It is noteworthy that palladium‐catalyzed benzylative C? S 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. |
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| Keywords: | cross‐coupling homogeneous catalysis palladium S O compounds synthetic methods |
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