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

preprint
submitted on 03.12.2020, 21:57 and posted on 07.12.2020, 05:37 by Wenhong Lin, Shea T. Meyer, Shawn Dormann, John D. Chisholm

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. Deuterium labeling studies indicate that a β-silyl carbocation intermediate is involved in the transformation.

History

Email Address of Submitting Author

jdchisho@syr.edu

Institution

Syracuse University

Country

USA

ORCID For Submitting Author

0000-0001-9518-2393

Declaration of Conflict of Interest

There are no conflicts to declare

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