63068-30-4

Upstream product

• 108-98-5 thiophenol 
• 62076-10-2 (tert-butylsulfinyl)benzene 
• 922-67-8 propynoic acid methyl ester 

Downstream Products

• 209787-91-7 [(R)-2-((S)-Benzenesulfinyl)-1-benzyl-ethyl]-carbamic acid tert-butyl ester 
• 209787-96-2 [(R)-2-((R)-Benzenesulfinyl)-1-benzyl-ethyl]-carbamic acid tert-butyl ester 
• 180999-35-3 [(S)-2-((S)-Benzenesulfinyl)-1-benzyl-ethyl]-carbamic acid tert-butyl ester 
• 181140-13-6 [(S)-2-((R)-Benzenesulfinyl)-1-benzyl-ethyl]-carbamic acid tert-butyl ester 

Relevant academic research and scientific papers

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 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.