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Zinc-Catalyzed Deoxygenation of Sulfoxides to Sulfides Applying [B(Pin)]2 as Deoxygenation Reagents

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Abstract

In the present study, the zinc-catalyzed deoxygenation of aliphatic and aromatic sulfoxides in the presence of 4,4,4′,4′,5,5,5′,5′-octamethyl-2,2′-bi-1,3,2-dioxaborolane [B(Pin)]2 as reducing reagent to produce the corresponding sulfides has been investigated. After examination of various reaction parameters the abilities of catalytic amounts of Zn(OTf)2 has been proven in the deoxygenation of various sulfoxides. Especially, a high functional group tolerance was noticed for the Zn(OTf)2/B(Pin)2 system.

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Acknowledgments

Financial support from the Cluster of Excellence “Unifying Concepts in Catalysis” (funded by the Deutsche Forschungsgemeinschaft and administered by the Technische Universität Berlin) is gratefully acknowledged.

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  1. Department of Chemistry, Cluster of Excellence “Unifying Concepts in Catalysis”, Technische Universität Berlin, Straße des 17. Juni 135/C2, 10623, Berlin, Germany

    Stephan Enthaler

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  1. Stephan Enthaler
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Correspondence to Stephan Enthaler.

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Enthaler, S. Zinc-Catalyzed Deoxygenation of Sulfoxides to Sulfides Applying [B(Pin)]2 as Deoxygenation Reagents. Catal Lett 142, 1306–1311 (2012). https://doi.org/10.1007/s10562-012-0897-y

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