TY - JOUR
T1 - Optimizing the Heck-Matsuda Reaction in Flow with a Constraint-Adapted Direct Search Algorithm
AU - Cortés-Borda, Daniel
AU - Kutonova, Ksenia V.
AU - Jamet, Corentin
AU - Trusova, Marina E.
AU - Zammattio, Françoise
AU - Truchet, Charlotte
AU - Rodriguez-Zubiri, Mireia
AU - Felpin, François Xavier
PY - 2016/11/18
Y1 - 2016/11/18
N2 - 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.
AB - 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.
KW - diazonium salts
KW - flow chemistry
KW - Heck reaction
KW - optimization algorithm
KW - palladium
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U2 - 10.1021/acs.oprd.6b00310
DO - 10.1021/acs.oprd.6b00310
M3 - Article
AN - SCOPUS:85011292267
VL - 20
SP - 1979
EP - 1987
JO - Organic Process Research and Development
JF - Organic Process Research and Development
SN - 1083-6160
IS - 11
ER -