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

07 December 2020, Version 1
This content is a preprint and has not undergone peer review at the time of posting.

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

Keywords

Esters
Protecting groups
Trichloroacetimidates
C-O Bond formation
b-Silyl Carbocations

Supplementary materials

Title
Description
Actions
Title
TMSE-EsterificationPaper-SI
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