Synthesis of esters by in situ formation and trapping of diazoalkanes

Richard A. Squitieri, Galen P. Shearn-Nance, Jason E. Hein, Jared T. Shaw

Research output: Contribution to journalArticle

12 Citations (Scopus)

Abstract

A general method has been developed for the in situ formation and trapping of diazoalkanes by carboxylic acids to form esters. The method is applicable to a large variety of carboxylic acids using diazo compounds that are formed from the hydrazones of benzaldehydes and aryl ketones. In situ reaction monitoring with IR spectroscopy (ReactIR) was used to demonstrate that slow addition of the hydrazone to a mixture of oxidant and carboxylic acid avoids the buildup of the diazo compound. This method enables the safe preparation of esters from simple precursors without isolation of diazo compounds.

Original languageEnglish (US)
Pages (from-to)5278-5284
Number of pages7
JournalJournal of Organic Chemistry
Volume81
Issue number13
DOIs
StatePublished - Jul 1 2016

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Carboxylic Acids
Hydrazones
Esters
Benzaldehydes
Ketones
Oxidants
Infrared spectroscopy
Monitoring

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Squitieri, R. A., Shearn-Nance, G. P., Hein, J. E., & Shaw, J. T. (2016). Synthesis of esters by in situ formation and trapping of diazoalkanes. Journal of Organic Chemistry, 81(13), 5278-5284. https://doi.org/10.1021/acs.joc.6b00408

Synthesis of esters by in situ formation and trapping of diazoalkanes. / Squitieri, Richard A.; Shearn-Nance, Galen P.; Hein, Jason E.; Shaw, Jared T.

In: Journal of Organic Chemistry, Vol. 81, No. 13, 01.07.2016, p. 5278-5284.

Research output: Contribution to journalArticle

Squitieri, RA, Shearn-Nance, GP, Hein, JE & Shaw, JT 2016, 'Synthesis of esters by in situ formation and trapping of diazoalkanes', Journal of Organic Chemistry, vol. 81, no. 13, pp. 5278-5284. https://doi.org/10.1021/acs.joc.6b00408
Squitieri, Richard A. ; Shearn-Nance, Galen P. ; Hein, Jason E. ; Shaw, Jared T. / Synthesis of esters by in situ formation and trapping of diazoalkanes. In: Journal of Organic Chemistry. 2016 ; Vol. 81, No. 13. pp. 5278-5284.
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