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

ASJC Scopus subject areas

  • Organic Chemistry

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    Mahajani, N. S., Meador, R. I. L., Smith, T. J., Canarelli, S. E., Adhikari, A. A., Shah, J. P., Russo, C. M., Wallach, D. R., Howard, K. T., Millimaci, A. M., & 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