Optimizing the Heck-Matsuda Reaction in Flow with a Constraint-Adapted Direct Search Algorithm

Daniel Cortés-Borda, Ksenia V. Kutonova, Corentin Jamet, Marina E. Trusova, Françoise Zammattio, Charlotte Truchet, Mireia Rodriguez-Zubiri, François Xavier Felpin

Research output: Contribution to journalArticle

30 Citations (Scopus)

Abstract

The optimization of a palladium-catalyzed Heck-Matsuda reaction using an optimization algorithm is presented. We modified and implemented the Nelder-Mead method in order to perform constrained optimizations in a multidimensional space. We illustrated the power of our modified algorithm through the optimization of a multivariable reaction involving the arylation of a deactivated olefin with an arenediazonium salt. The great flexibility of our optimization method allows to fine-tune experimental conditions according to three different objective functions: maximum yield, highest throughput, and lowest production cost. The beneficial properties of flow reactors associated with the power of intelligent algorithms for the fine-tuning of experimental parameters allowed the reaction to proceed in astonishingly simple conditions unable to promote the coupling through traditional batch chemistry.

Original languageEnglish
Pages (from-to)1979-1987
Number of pages9
JournalOrganic Process Research and Development
Volume20
Issue number11
DOIs
Publication statusPublished - 18 Nov 2016

Keywords

  • diazonium salts
  • flow chemistry
  • Heck reaction
  • optimization algorithm
  • palladium

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Organic Chemistry

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    Cortés-Borda, D., Kutonova, K. V., Jamet, C., Trusova, M. E., Zammattio, F., Truchet, C., Rodriguez-Zubiri, M., & Felpin, F. X. (2016). Optimizing the Heck-Matsuda Reaction in Flow with a Constraint-Adapted Direct Search Algorithm. Organic Process Research and Development, 20(11), 1979-1987. https://doi.org/10.1021/acs.oprd.6b00310