Synthesis of α-germyl and α-silylcarboxylic acids and selected electrochemical oxidations

Rakovshik, Anna; Shtelman, Alex V.; Becker, James Y.

doi:10.1016/j.jorganchem.2011.12.025

Cited by 3 publications

(1 citation statement)

References 15 publications

(33 reference statements)

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“…To the best of our knowledge, TBAILs have never been used with trimethylsilyl acetate (TMSOAc) for acetylation reaction. Usually, trimethylsilyl acetate has been used for the preparation of by-product free oligosiloxane [20], α-silyl carboxylic acid [21], and silyl ketene acetals [22]. Recently, our lab reported that trimethylsilyl acetate was used for the silylation of sugars in the presence of a base [23].…”

Section: Introductionmentioning

confidence: 99%

Mild and Efficient Tunable Brønsted Acidic Ionic Liquid Catalyzed O-Acetylation and O-Trimethylsilylation with Trimethylsilyl Acetate (TMSOAc) and Hexamethyldisilazane (HMDS)

et al. 2021

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This report discloses a mild and efficient O-acetylation using easily accessible TMSOAc as a novel acetyl reagent and O-trimethylsilylation using HMDS for various alcohols catalyzed by tunable Brønsted acidic ionic liquids (TBAILs). Imidazolium-based TBAILs were prepared by a two-step atom-economic reaction and acidities measured by using UV-visible spectroscopy. Both protections for alcohols were accomplished at room temperature with good to excellent yields, while the products and TBAILs were separated by simple work-up for O-silylation and column chromatography for O-acetylation. Notably, with the simple post-process, TBAILs catalyst in this solvent free method easily recovered and recycled several times without significant degradation.

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