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tert -Butyl Sulfoxides: Key Precursors for Palladium-Catalyzed Arylation of Sulfenate Salts

Abstract : The present report describes an efficient and clean generation of sulfenate salts (R1SO−) by pyrolysis of readily available tert‐butyl sulfoxides to give sulfenic acids (R1SOH) and traceless isobutene, followed by hydrogen abstraction with a weak inorganic base (K3PO4). The relevance of this process was exemplified through an in situ palladium‐catalyzed cross‐coupling reaction with aryl halides/triflates leading to aryl sulfoxides. The operationally simple CS bond‐forming protocol developed uses Pd(dba)2 as catalyst and Xantphos as ligand in toluene or a toluene/H2O mixture. Further extensions include the use of di‐tert‐butyl sulfoxide as an equivalent for sulfur monoxide dianion (SO2−) and the development of diastereoselective versions in the [2.2]paracyclophane and biaryl series.
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https://hal-normandie-univ.archives-ouvertes.fr/hal-01830250
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Submitted on : Wednesday, July 4, 2018 - 5:52:22 PM
Last modification on : Thursday, July 2, 2020 - 3:21:37 AM

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Fabien Gelat, Jean-François Lohier, Annie-Claude Gaumont, Stéphane Perrio. tert -Butyl Sulfoxides: Key Precursors for Palladium-Catalyzed Arylation of Sulfenate Salts. Advanced Synthesis and Catalysis, Wiley-VCH Verlag, 2015, 357 (9), pp.2011 - 2016. ⟨10.1002/adsc.201500368⟩. ⟨hal-01830250⟩

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