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

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 ion with a weak inorganic base (K3PO4). The relevance of this process was exe...

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Bibliographic Details
Published in:Advanced synthesis & catalysis 2015-06, Vol.357 (9), p.2011-2016
Main Authors: Gelat, Fabien, Lohier, Jean-François, Gaumont, Annie-Claude, Perrio, Stéphane
Format: Article
Language:English
Subjects:
Aromatic compounds
Bonding
Chemical Sciences
Cleaning
cross-coupling
diastereoselectivity
Equivalence
Ligands
Organic chemistry
palladium
Precursors
Pyrolysis
sulfenate salts
sulfoxides
Toluene
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Summary: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 ion 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.
ISSN:1615-4150
1615-4169
DOI:10.1002/adsc.201500368