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

17 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

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optimization
Constrained optimization
Palladium
Alkenes
production costs
Tuning
Salts
Throughput
alkenes
palladium
flexibility
tuning
reactors
chemistry
salts
Costs

Keywords

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

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Organic Chemistry

Cite this

Optimizing the Heck-Matsuda Reaction in Flow with a Constraint-Adapted Direct Search Algorithm. / Cortés-Borda, Daniel; Kutonova, Ksenia V.; Jamet, Corentin; Trusova, Marina E.; Zammattio, Françoise; Truchet, Charlotte; Rodriguez-Zubiri, Mireia; Felpin, François Xavier.

In: Organic Process Research and Development, Vol. 20, No. 11, 18.11.2016, p. 1979-1987.

Research output: Contribution to journalArticle

Cortés-Borda, D, Kutonova, KV, Jamet, C, Trusova, ME, Zammattio, F, Truchet, C, Rodriguez-Zubiri, M & Felpin, FX 2016, 'Optimizing the Heck-Matsuda Reaction in Flow with a Constraint-Adapted Direct Search Algorithm', Organic Process Research and Development, vol. 20, no. 11, pp. 1979-1987. https://doi.org/10.1021/acs.oprd.6b00310
Cortés-Borda, Daniel ; Kutonova, Ksenia V. ; Jamet, Corentin ; Trusova, Marina E. ; Zammattio, Françoise ; Truchet, Charlotte ; Rodriguez-Zubiri, Mireia ; Felpin, François Xavier. / Optimizing the Heck-Matsuda Reaction in Flow with a Constraint-Adapted Direct Search Algorithm. In: Organic Process Research and Development. 2016 ; Vol. 20, No. 11. pp. 1979-1987.
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