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Diaryl Sulfoxides from Aryl Benzyl Sulfoxides: A Single Palladium-Catalyzed Triple Relay Process

Authors


  • We thank the National Science Foundation [CHE-0848460 (GOALI) and 1152488] for financial support. K.E.B thanks the Université Pierre et Marie Curie and CROUS de Paris for financial support. B.Z. thanks the China Scholarship Council [2011635137] for financial support.

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[BOND]S bond cleavage, and C[BOND]S bond formation. The byproduct benzophenone is formed by an additional palladium-catalyzed process. It is noteworthy that palladium-catalyzed benzylative C[BOND]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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