2060-65-3Relevant articles and documents
Benzaldehyde- And Nickel-Catalyzed Photoredox C(sp3)-H Alkylation/Arylation with Amides and Thioethers
Si, Xiaojia,Zhang, Lumin,Hashmi, A. Stephen K.
supporting information, p. 6329 - 6332 (2019/08/20)
Herein a synergistic combination of a nickel catalyst and benzaldehyde for the utilization of amides and thioethers in C(sp3)-H alkylation and arylation reactions employing simple aryl or alkyl halides is reported. This method provides a simple and cheap strategy for the direct functionalization of amides and thioethers. Readily available starting materials, mild reaction conditions, a good functional-group tolerance, and a broad substrate scope make this methodology attractive and practical for pharmaceutical and synthetic chemistry.
3-Lithiopropyl tert-Butyl Thioether: A New γ-Functionalised Organolithium Compound (d3-Reagent) in Synthetic Organic Chemistry
Almena, Juan,Foubelo, Francisco,Yus, Miguel
, p. 11883 - 11890 (2007/10/02)
The reaction of 3-bromo or 3-chloropropyl tert-butyl thioether (1a or 1'a) with and excess of lithium powder and a catalytic amount of naphthalene (2.5 mol percent) in THF at -78 deg C followed by treatment with an electrophile (H2O, D2O, Me2S2, CO2) at the same temperature leads, after hydrolysis, to the expected products 2.ALternatively the process can be carried out under Barbier-type reaction conditions tCHO, PhCHO, Me2CO, (CH2)4CO, (CH2)5CO, PhCOMe, c-C3H5COPh> and using DTBB as the arene catalyst at 0 deg C.De-tert-butylation of products 2 with mercury(II) acetate and sulfhydric acid yields different sulfurated derivatives depending on the structure of the starting thioether.
