2013
DOI: 10.1021/op300275p
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Beyond the Numbers: Charting Chemical Reaction Space

Abstract: We present here an informed estimate of the millions of parameter settings that might be required to optimise one typical transition-metal-catalysed reaction. We describe briefly how both Design of Experiments (DoE) and Principal Component Analysis (PCA) techniques may be combined to reduce the number of potential reaction settings to a practical number of experiments without losing critical information. A key feature of this approach is the ability to relate discrete or discontinuous parameters to one another… Show more

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Cited by 82 publications
(78 citation statements)
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References 49 publications
(19 reference statements)
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“…Hence, NMP was the solvent of choice in the synthesis of 4‐morpholino‐substituted 1,8‐naphthalimide 5 , and DMSO in the synthesis of 4‐morpholino‐substituted 1,8‐naphthalimide 6 . We then used statistical experimental design20–24 to optimize the reaction of 4‐morpholino‐substituted 1,8‐naphthalimide 5 . By varying the temperature (150, 175, and 200 °C), reaction time (60, 90, and 120 min), and equivalents of substrates (1:1:1, 1:1:2, 1:2:1, and 1:2:2 ratio of 1 / 4 / 2 ), and measuring yield as a response, a D‐optimal design25 with 25 experimental runs (i.e., 22 different experiments and three replicates) were created using MODDE software 9.1.1.0 (MKS Umetrics AB, Sweden); the results are shown in Table 2 and Figure 2.…”
Section: Resultsmentioning
confidence: 99%
“…Hence, NMP was the solvent of choice in the synthesis of 4‐morpholino‐substituted 1,8‐naphthalimide 5 , and DMSO in the synthesis of 4‐morpholino‐substituted 1,8‐naphthalimide 6 . We then used statistical experimental design20–24 to optimize the reaction of 4‐morpholino‐substituted 1,8‐naphthalimide 5 . By varying the temperature (150, 175, and 200 °C), reaction time (60, 90, and 120 min), and equivalents of substrates (1:1:1, 1:1:2, 1:2:1, and 1:2:2 ratio of 1 / 4 / 2 ), and measuring yield as a response, a D‐optimal design25 with 25 experimental runs (i.e., 22 different experiments and three replicates) were created using MODDE software 9.1.1.0 (MKS Umetrics AB, Sweden); the results are shown in Table 2 and Figure 2.…”
Section: Resultsmentioning
confidence: 99%
“…The use of trifluoroacetic acid in acetonitrile gave high conversion, but unfortunately also led to the formation of byproducts, whereas the use of acetic acid as solvent proved to be the most promising of the evaluated acidic conditions, and pyridine as solvent was found to provide the most effective basic condi- Next, statistical experimental design [17][18][19][20][21] was employed to optimize the reaction under different conditions. Various acids (acetic acid, p-toluenesulfonic acid, trifluoroacetic acid, and pyridinium p-toluenesulfonate) were next evaluated in different amounts and solvents.…”
Section: Resultsmentioning
confidence: 99%
“…solvent) essentially results in a different reaction because every single metal/ligand/solvent combination is effectively a different catalyst system, albeit for the same reaction. This means there are an especially large number of permutations possible for transition metal catalysed reactions …”
Section: Design Of Experimentsmentioning
confidence: 99%
“…This is particularly the case for homogeneous catalysis because of the large number of parameters that can be controlled or varied in this type of catalytic reaction. Indeed, we recently published a study which demonstrated just how many permutations there can be for a single catalytic reaction, even with the same pair of substrates . Typical parameters for a catalytic reaction are listed in Table in two groups, continuous and discrete (or discontinuous) parameters.…”
Section: Introductionmentioning
confidence: 99%
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