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

Research output: Contribution to journalArticle

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 languageEnglish (US)
Pages (from-to)7871-7882
Number of pages12
JournalJournal of Organic Chemistry
Volume84
Issue number12
DOIs
StatePublished - Jun 21 2019

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Esters
Chemical activation
Substrates
Functional groups
Decomposition
Heating
Acids
Electrons
trichloroacetamide

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Mahajani, N. S., Meador, R. I. L., Smith, T. J., Canarelli, S. E., Adhikari, A. A., Shah, J. P., ... Chisholm, J. D. (2019). Ester Formation via Symbiotic Activation Utilizing Trichloroacetimidate Electrophiles. Journal of Organic Chemistry, 84(12), 7871-7882. https://doi.org/10.1021/acs.joc.9b00745

Ester Formation via Symbiotic Activation Utilizing Trichloroacetimidate Electrophiles. / Mahajani, Nivedita S.; Meador, Rowan I.L.; Smith, Tomas J.; Canarelli, Sarah E.; Adhikari, Arijit A.; Shah, Jigisha P.; Russo, Christopher M.; Wallach, Daniel R.; Howard, Kyle T.; Millimaci, Alexandra M.; Chisholm, John D.

In: Journal of Organic Chemistry, Vol. 84, No. 12, 21.06.2019, p. 7871-7882.

Research output: Contribution to journalArticle

Mahajani, NS, Meador, RIL, Smith, TJ, Canarelli, SE, Adhikari, AA, Shah, JP, Russo, CM, Wallach, DR, Howard, KT, Millimaci, AM & Chisholm, JD 2019, 'Ester Formation via Symbiotic Activation Utilizing Trichloroacetimidate Electrophiles', Journal of Organic Chemistry, vol. 84, no. 12, pp. 7871-7882. https://doi.org/10.1021/acs.joc.9b00745
Mahajani NS, Meador RIL, Smith TJ, Canarelli SE, Adhikari AA, Shah JP et al. Ester Formation via Symbiotic Activation Utilizing Trichloroacetimidate Electrophiles. Journal of Organic Chemistry. 2019 Jun 21;84(12):7871-7882. https://doi.org/10.1021/acs.joc.9b00745
Mahajani, Nivedita S. ; Meador, Rowan I.L. ; Smith, Tomas J. ; Canarelli, Sarah E. ; Adhikari, Arijit A. ; Shah, Jigisha P. ; Russo, Christopher M. ; Wallach, Daniel R. ; Howard, Kyle T. ; Millimaci, Alexandra M. ; Chisholm, John D. / Ester Formation via Symbiotic Activation Utilizing Trichloroacetimidate Electrophiles. In: Journal of Organic Chemistry. 2019 ; Vol. 84, No. 12. pp. 7871-7882.
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