One-pot preparation of Julia-Kocienski sulfides and sulfones from alcohols

• Published in: Tetrahedron letters 2019-09, Vol.60 (36), p.151017, Article 151017
• Main Authors: Ando, Kaori, Hattori, Junichiro
• Format: Article
• Language: English
• Subjects: Julia-Kocienski reagents; One-pot reaction; Sulfides from alcohols; Sulfones from alcohols
• ISSN: 0040-4039; 1873-3581
• DOI: 10.1016/j.tetlet.2019.151017

[Display omitted] •One-pot reaction.•Preparation of Julia-Kocienski sulfides from alcohols.•Preparation of Julia-Kocienski sulfones from alcohols.•Useful for alkene synthesis. A method for one-pot preparation of Julia-Kocienski sulfides and sulfones from alcohols and thiols is reported. A variety of primary alcohols were converted to the corresponding mesylates by methansulfonyl chloride and triethylamine in THF. After the reaction is complete, thiol (1 or 10) and either NaH or t-BuOK were added. The Julia-Kocienski sulfides 3, 9 and 11 were prepared by one-pot two steps procedure from alcohols in 76–96% yields (16 examples). Furthermore, after the sulfide formation, the reaction mixture was neutralized by p-toluenesulfonic acid and treated with H2O2 and ammonium molybdate in EtOH to give the Julia-Kocienski sulfones 4 in good yields except for trans-2-hexen-1-ol.