Ester Formation via Symbiotic Activation Utilizing Trichloroacetimidate Electrophiles

Nivedita S. Mahajani; Rowan I.L. Meador; Tomas J. Smith; Sarah E. Canarelli; Arijit A. Adhikari; Jigisha P. Shah; Christopher M. Russo; Daniel R. Wallach; Kyle T. Howard; Alexandra M. Millimaci; John D. Chisholm

doi:10.1021/acs.joc.9b00745

Ester Formation via Symbiotic Activation Utilizing Trichloroacetimidate Electrophiles

Nivedita S. Mahajani, Rowan I.L. Meador, Tomas J. Smith, Sarah E. Canarelli, Arijit A. Adhikari, Jigisha P. Shah, Christopher M. Russo, Daniel R. Wallach, Kyle T. Howard, Alexandra M. Millimaci, John D. Chisholm

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14 Scopus citations

Abstract

Trichloroacetimidates are useful reagents for the synthesis of esters under mild conditions that do not require an exogenous promoter. These conditions avoid the undesired decomposition of substrates with sensitive functional groups that are often observed with the use of strong Lewis or Brønsted acids. With heating, these reactions have been extended to benzyl esters without electron-donating groups. These inexpensive and convenient methods should find application in the formation of esters in complex substrates.

Original language	English (US)
Pages (from-to)	7871-7882
Number of pages	12
Journal	Journal of Organic Chemistry
Volume	84
Issue number	12
DOIs	https://doi.org/10.1021/acs.joc.9b00745
State	Published - Jun 21 2019

ASJC Scopus subject areas

Organic Chemistry

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title = "Ester Formation via Symbiotic Activation Utilizing Trichloroacetimidate Electrophiles",

abstract = "Trichloroacetimidates are useful reagents for the synthesis of esters under mild conditions that do not require an exogenous promoter. These conditions avoid the undesired decomposition of substrates with sensitive functional groups that are often observed with the use of strong Lewis or Br{\o}nsted acids. With heating, these reactions have been extended to benzyl esters without electron-donating groups. These inexpensive and convenient methods should find application in the formation of esters in complex substrates.",

author = "Mahajani, {Nivedita S.} and Meador, {Rowan I.L.} and Smith, {Tomas J.} and Canarelli, {Sarah E.} and Adhikari, {Arijit A.} and Shah, {Jigisha P.} and Russo, {Christopher M.} and Wallach, {Daniel R.} and Howard, {Kyle T.} and Millimaci, {Alexandra M.} and Chisholm, {John D.}",

note = "Publisher Copyright: {\textcopyright} 2019 American Chemical Society.",

year = "2019",

month = jun,

day = "21",

doi = "10.1021/acs.joc.9b00745",

language = "English (US)",

volume = "84",

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T1 - Ester Formation via Symbiotic Activation Utilizing Trichloroacetimidate Electrophiles

AU - Mahajani, Nivedita S.

AU - Meador, Rowan I.L.

AU - Smith, Tomas J.

AU - Canarelli, Sarah E.

AU - Adhikari, Arijit A.

AU - Shah, Jigisha P.

AU - Russo, Christopher M.

AU - Wallach, Daniel R.

AU - Howard, Kyle T.

AU - Millimaci, Alexandra M.

AU - Chisholm, John D.

PY - 2019/6/21

Y1 - 2019/6/21

N2 - Trichloroacetimidates are useful reagents for the synthesis of esters under mild conditions that do not require an exogenous promoter. These conditions avoid the undesired decomposition of substrates with sensitive functional groups that are often observed with the use of strong Lewis or Brønsted acids. With heating, these reactions have been extended to benzyl esters without electron-donating groups. These inexpensive and convenient methods should find application in the formation of esters in complex substrates.

AB - Trichloroacetimidates are useful reagents for the synthesis of esters under mild conditions that do not require an exogenous promoter. These conditions avoid the undesired decomposition of substrates with sensitive functional groups that are often observed with the use of strong Lewis or Brønsted acids. With heating, these reactions have been extended to benzyl esters without electron-donating groups. These inexpensive and convenient methods should find application in the formation of esters in complex substrates.

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ER -

Ester Formation via Symbiotic Activation Utilizing Trichloroacetimidate Electrophiles

Abstract

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