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 language | English |
|---|---|
| Pages (from-to) | 1979-1987 |
| Number of pages | 9 |
| Journal | Organic Process Research and Development |
| Volume | 20 |
| Issue number | 11 |
| DOIs | |
| Publication status | Published - 18 Nov 2016 |
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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 journal › Article
}
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
UR - http://www.scopus.com/inward/record.url?scp=85011292267&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=85011292267&partnerID=8YFLogxK
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 -