Facile electrochemical synthesis of silyl acetals: An air-stable precursor to formylsilane. (17th August 2022)

• Record Type: Journal Article
• Authors: Noji, Masahiro; Ishimaru, Sho; Obata, Haruki; Kumaki, Ayano; Seki, Taichi; Hayashi, Satoshi; Takanami, Toshikatsu
• Is Part Of: Tetrahedron letters. Volume 104(2022)
• Publication Date: 2022-08-17
• Subjects: Anodic oxidation -- Silyl dithiane -- Silyl acetal -- Formylsilane; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tetlet.2022.154026
• Languages: English
• ISSNs: 0040-4039

Abstract

Graphical abstract: Highlights: Acylsilanes are versatile synthons in synthetic organic chemistry. The simplest class of acylsilane, formylsilane, is unstable and difficult to prepare. Electrochemical oxidation of silyl dithianes with alcohol gave silyl acetals. The silyl acetal can be readily converted to the corresponding formylsilane. A greener alternative to the traditional mercury-mediated synthesis of formylsilane. Abstract: A facile electrochemical synthesis of silyl acetal, a synthetic equivalent of formylsilane, was described in this study. Using undivided cells and platinum and stainless-steel electrodes, the constant current electrolysis of 2-silyl-1, 3‑dithiane with monoalcohol and diol in acetonitrile yielded various silyl acetals. The silyl acetal was readily converted to the corresponding formylsilane. This method without mercury reagents would be a greener alternative to traditional formylsilane synthesis.