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Research Article Open access CC BY 4.0

Esterifications with 2-(Trimethylsilyl)ethyl 2,2,2-Trichloroacetimidate

Wenhong Lin, Shea Meyer, Shawn Dormann, John Chisholm

Organics · pp. 17–25 · Published 4 Feb 2021

10.3390/org2010002

Abstract

2-(Trimethylsilyl)ethyl 2,2,2-trichloroacetimidate is readily synthesized from 2-trimethylsilylethanol in high yield. This imidate is an effective reagent for the formation of 2-trimethylsilylethyl esters without the need for an exogenous promoter or catalyst, as the carboxylic acid substrate is acidic enough to promote ester formation without an additive. A deuterium labeling study indicated that a β-silyl carbocation intermediate is involved in the transformation.

Carbocation Trimethylsilyl Chemistry Silylation Yield (engineering) Reagent Catalysis Substrate (aquarium)

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Cited by 2

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