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

Daniel Cortes-Borda (1, 2) , Ksenia V. Kutonova (3) , Corentin Jamet (1) , Marina E. Trusova (3) , Francoise Zammattio (2) , Charlotte Truchet (2, 1) , Mireia Rodriguez-Zubiri (2) , Francois-Xavier Felpin (1)

1 LINA - Laboratoire d'Informatique de Nantes Atlantique
2 CEISAM - Chimie Et Interdisciplinarité : Synthèse, Analyse, Modélisation
3 UPT - Tomsk Polytechnic University [Russie]

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.

Domaines: Chimie

Daniel Cortes-Borda, Ksenia V. Kutonova, Corentin Jamet, Marina E. Trusova, Francoise Zammattio, et al.. Optimizing the Heck-Matsuda Reaction in Flow with a Constraint-Adapted Direct Search Algorithm. Organic Process Research and Development, 2016, 20 (11), pp.1979-1987. ⟨10.1021/acs.oprd.6b00310⟩. ⟨hal-02141343⟩