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

Wenhong Lin; Shea T. Meyer; Shawn Dormann; John D. Chisholm

doi:10.3390/org2010002

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

Wenhong Lin, Shea T. Meyer, Shawn Dormann, John D. Chisholm

Research output: Contribution to journal › Article › peer-review

1 Scopus citations

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.

Original language	English (US)
Pages (from-to)	17-25
Number of pages	9
Journal	Organics
Volume	2
Issue number	1
DOIs	https://doi.org/10.3390/org2010002
State	Published - Mar 2021

Keywords

C-O bond formation
esters
protecting groups
trichloroacetimidates
β-silyl carbocations

ASJC Scopus subject areas

Organic Chemistry

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10.3390/org2010002

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title = "Esterifications with 2-(Trimethylsilyl)ethyl 2,2,2-Trichloroacetimidate",

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.",

keywords = "C-O bond formation, esters, protecting groups, trichloroacetimidates, β-silyl carbocations",

author = "Wenhong Lin and Meyer, {Shea T.} and Shawn Dormann and Chisholm, {John D.}",

note = "Publisher Copyright: {\textcopyright} 2021 by the authors.",

year = "2021",

month = mar,

doi = "10.3390/org2010002",

language = "English (US)",

volume = "2",

pages = "17--25",

journal = "Organics",

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T1 - Esterifications with 2-(Trimethylsilyl)ethyl 2,2,2-Trichloroacetimidate

AU - Lin, Wenhong

AU - Meyer, Shea T.

AU - Dormann, Shawn

AU - Chisholm, John D.

PY - 2021/3

Y1 - 2021/3

N2 - 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.

AB - 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.

KW - C-O bond formation

KW - esters

KW - protecting groups

KW - trichloroacetimidates

KW - β-silyl carbocations

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JO - Organics

JF - Organics

IS - 1

ER -

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

Abstract

Keywords

ASJC Scopus subject areas

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