Impact of Design of Experiments in the Optimisation of Catalytic Reactions in Academia

Abstract

Design of Experiments (DoE) is extensively and routinely used in industry; however, in recent decades, it has gained increasing interest from academia in organic synthesis. The use of chemometrics is an attractive strategy to find the real optimum in chemical reactions, especially when affected by several variables. DoE has been applied in a growing number of synthetic transformations over the years, where it undoubtedly helps in the process of optimisation, saving costs and time. This review concisely discusses the chemometric basis of Design of Experiments and highlights several examples in which DoE is applied in organic synthesis.

1 Introduction

2 Chemometric Basis of DoE

3 DoE Applied in Catalysis: Selected Examples

3.1 DoE in Metal Catalysis

3.2 DoE in Biocatalysis

3.3 DoE in Organocatalysis

4 Conclusions

Key words

DoE - design - chemometrics - optimisation - screening - organic synthesis - catalysis

Publication History

Received: 02 December 2021

Accepted after revision: 11 January 2022

Accepted Manuscript online:
11 January 2022

Article published online:
21 February 2022

• References

• 1 Fisher RA. The Design of Experiments . Hafner Publishing Company, Inc; New York: 1935

For selected examples on the application of DoE in industry, see:
• 2a Owen M, Godbert S. Org. Process Res. Dev. 2001; 5: 324
• 2b Laird T. Org. Process Res. Dev. 2002; 6: 337
• 2c Tye H, Whittaker M. Org. Biomol. Chem. 2004; 2: 813
• 2d Guercio G, Perboni A, Tinazzi F, Rovatti L, Provera S. Org. Process Res. Dev. 2010; 14: 840
• 2e Murray PM, Tyler SN. G, Moseley JD. Org. Process Res. Dev. 2013; 17: 40
• 2f Stone S, Wang T, Liang J, Cochran J, Green J, Gu W. Org. Biomol. Chem. 2015; 13: 10471
• 2g Weissman SA, Anderson NG. Org. Process Res. Dev. 2015; 19: 1605

For selected examples on the application of DoE in academia, see:
• 3a Jamieson C, Congreve MS, Emiabata-Smith DF, Ley SV. Synlett 2000; 1603
• 3b Jamieson C, Congreve MS, Emiabata-Smith DF, Ley SV, Scicinski JJ. Org. Process Res. Dev. 2002; 6: 823
• 3c Evans MD, Ring J, Schoen A, Bell A, Edwards P, Berthelot D, Nicewonger R, Baldino CM. Tetrahedron Lett. 2003; 44: 9337
• 3d Veum L, Pereira SR. M, Van der Waal JC, Hanefeld U. Eur. J. Org. Chem. 2006; 1664
• 3e Glasnow TN, Tye H, Kappe CO. Tetrahedron 2008; 64: 2035
• 3f Hajzer V, Alexy P, Latika A, Durmis J, Šebesta R. Monatsh. Chem. 2015; 146: 1541
• 3g Ekebergh A, Lingblom C, Sandin P, Wennerås C, Mårtensson J. Org. Biomol. Chem. 2015; 13: 3382
• 3h Caldwell N, Jamieson C, Simpson I, Watson AJ. B. Chem. Commun. 2015; 51: 9495

For reviews and articles on DoE and a deeper discussion on mathematical and statistical aspects, please see:
• 4a Box GE. P, Draper NR. In Empirical Model-Building and Response Surfaces . John Wiley & Sons; New York: 1986
• 4b Lundstedt T, Seifert E, Abramo L, Thelin B, Nyström Å, Pettersen J, Bergman R. Chemom. Intell. Lab. Syst. 1998; 42: 3
• 4c Carlson R. Chemom. Intell. Lab. Syst. 2004; 73: 151
• 4d Tye H. Drug Discovery Today 2004; 9: 485
• 4e Carlson R, Carlson JE. In Data Handling in Science and Technology, Vol. 24. Rutan S, Walczak B. Elsevier; Amsterdam: 2005
• 4f Leardi R. Anal. Chim. Acta 2009; 652: 161
• 4g Ardini F, Soggia F, Rugi F, Udisti R, Grotti M. Anal. Chim. Acta 2010; 678: 18
• 4h Dejaegher B, Vander Heyden Y. J. Pharm. Biomed. Anal. 2011; 56: 141
• 4i Di Carro M, Ardini F, Magi F. Microchem. J. 2015; 121: 172
• 4j Westad F, Marini F. Anal. Chim. Acta 2015; 893: 14
• 4k Brereton RG, Jansen J, Lopes J, Marini F, Pomerantsev A, Rodionova O, Roger JM, Walczak B, Tauler R. Anal. Bioanal. Chem. 2017; 409: 589
• 4l Brereton RG, Jansen J, Lopes J, Marini F, Pomerantsev A, Rodionova O, Roger JM, Walczak B, Tauler R. Anal. Bioanal. Chem. 2018; 410: 6691
• 4m Debevec V, Srčič S, Horvat M. Drug Dev. Ind. Pharm. 2018; 44: 566
• 4n Weese ML, Ramsey PJ, Montgomery DC. Appl. Stochastic Models Bus. Ind. 2018; 34: 244
• 4o Mishra P, Biancolillo A, Roger JM, Marini F, Rutledge DN. Trends Anal. Chem. 2020; 132: 116045
• 5a Leardi R. In Chemometrics in Food Chemistry, Vol. 28. Marini F. Elsevier; Amsterdam: 2013: 9
• 5b Benedetti B, Caponigro V, Ardini F. Crit. Rev. Anal. Chem. 2020; 1

For selected examples on the application of DoE in organic chemistry, see:
• 6a Carlson R, Lundstedt T, Albano C. Acta Chem. Scand., Ser. B 1985; 39: 79
• 6b Carlson R, Lundstedt T, Shabana R. Acta Chem. Scand., Ser. B 1986; 40: 694
• 6c Carlson R, Nordahl A, Barth T, Myklebust R. Chemom. Intell. Lab. Syst. 1992; 12: 237
• 6d Carlson R, Lejon T, Lundstedt T, Le Clouerec E. Acta Chem. Scand. 1993; 47: 1046
• 6e Carlson R, Hudlicky T. Helv. Chim. Acta 2012; 95: 2052
• 6f Murray PM, Bellany F, Benhamou L, Bučar D.-K, Tabor AB, Sheppard TD. Org. Biomol. Chem. 2016; 14: 2373
• 6g Renzi P, Bella M. Synlett 2017; 28: 306
• 7a Plackett RL, Burman JP. Biometrika 1946; 33: 305
• 7b Ahuja SK, Ferreira GM, Moreira AR. Biotechnol. Bioeng. 2004; 85: 666
• 8 Gottipati R, Mishra S. Chem. Eng. J. 2010; 160: 99
• 9a Box GE. P, Hunter JS. Technometrics 1961; 3: 311
• 9b Box GE. P, Hunter JS, Hunter WG. Statistics for Experimenters: An Introduction to Design, Data Analysis and Model Building. John Wiley & Sons; New York: 1978
• 10a Bezerra MA, Santelli RE, Oliveira EP, Villar LS, Escaleira LA. Talanta 2008; 76: 965
• 10b Hibbert DB. J. Chromatogr. B 2012; 910: 2
• 10c Candioti LV, De Zan MM, Camara MS, Goicoechea HC. Talanta 2014; 124: 123
• 11a Box GE. P, Wilson KB. J. R. Stat. Soc., B 1951; 13: 1
• 11b Box GE. P. Biometrics 1954; 10: 16
• 11c Box GE. P, Youle PV. Biometrics 1955; 11: 287
• 11d Box GE. P, Hunter JS. Ann. Math. Stat. 1957; 28: 195
• 12a Box GE. P, Behnken DW. Technometrics 1960; 2: 455
• 12b Ferreira SL. C, Bruns RE, Ferreira HS, Matos GD, David JM, Brandão GC, da Silva EG. P, Portugal LA, dos Reis PS, Souza AS. Anal. Chim. Acta 2007; 597: 179
• 13a Doehlert DH. Appl. Stat. 1970; 13: 231
• 13b Sarabia LA, Ortiz MC. In Comprehensive Chemometrics: Chemical and Biochemical Data Analysis. Elsevier; Amsterdam: 2009
• 14a Atkinson AC, Tobias RD. J. Chromatogr. A 2008; 1177: 1
• 14b Leardi R. In Encyclopedia of Analytical Chemistry . John Wiley & Sons; Chichester: 2018
• 15 Harper KC, Sigman MS. Science 2011; 333: 1875
• 16 García-Cabeza AL, Marín-Barrios R, Azarken R, Moreno-Dorado FJ, Ortega MJ, Vidal H, Gatica JM, Massanet GM, Guerra FM. Eur. J. Org. Chem. 2013; 36: 8307
• 17 Perez CC, Pena JM, Correia CR. D. New J. Chem. 2014; 38: 3933
• 18 Sontakke JB, Yadav GD. Ind. Eng. Chem. Res. 2011; 50: 12975
• 19 Silvi M, Renzi P, Rosato D, Margarita C, Vecchioni A, Bordacchini I, Morra D, Nicolosi A, Cari R, Sciubba F, Scarpino Schietroma DM, Bella M. Chem. Eur. J. 2013; 19: 9973
• 20 Renzi P, Kronig C, Carlone A, Eröksüz S, Berkessel A, Bella M. Chem. Eur. J. 2014; 20: 11768
• 21 Berkessel A, Cleemann F, Mukherjee S. Angew. Chem. Int. Ed. 2005; 44: 7466