期刊
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
卷 53, 期 1, 页码 260-264出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201307172
关键词
cross-coupling; homogeneous catalysis; palladium; SO compounds; synthetic methods
资金
- National Science Foundation [CHE-0848460 (GOALI), 1152488]
- Universite Pierre et Marie Curie and CROUS de Paris
- China Scholarship Council [2011635137]
- Division Of Chemistry
- Direct For Mathematical & Physical Scien [1152488] Funding Source: National Science Foundation
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 -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.
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