Deoxygenation of tertiary and secondary alcohols with sodium borohydride, trimethylsilyl chloride, and potassium iodide in acetonitrile. (7th December 2021)

• Record Type: Journal Article
• Authors: Kato, Yuichi; Inoue, Tomoka; Furuyama, Yuuki; Ohgane, Kenji; Sadaie, Mahito; Kuramochi, Kouji
• Is Part Of: Tetrahedron letters. Volume 86(2021)
• Publication Date: 2021-12-07
• Subjects: Deoxygenation -- Carbocation -- Sodium borohydride -- Trimethylsilyl chloride -- Potassium iodide; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tetlet.2021.153519
• Languages: English
• ISSNs: 0040-4039

Abstract

Graphical abstract: Abstract: The deoxygenation of tertiary and secondary alcohols to give the corresponding alkanes is conventionally performed using an organosilane and a strong acid. In this study, a deoxygenation method was developed for tertiary and secondary alcohols, using trimethylsilane and trimethylsilyl iodide generated in situ from sodium borohydride and trimethylsilyl chloride, and trimethylsilyl chloride and potassium iodide, respectively. With our method, tertiary and secondary alcohols, which provided stable carbocations, were converted into the corresponding alkanes. This paper also presents the optimization of the reaction conditions, the reaction mechanism, as well as the scope and limitations of the method.