An automated continuous-flow platform for the estimation of multistep reaction kinetics

Organic Process Research and Development

Volumn 16, Issue 11, 2012, Pages 1770-1782

  Reizman, Brandon J ^a   Jensen, Klavs F ^a  

^a Massachusetts Institute of Technology Cambridge   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AUTOMATED SYSTEMS; CHEMICAL SYNTHESIS; CONTINUOUS-FLOW; CONTINUOUS-FLOW SYSTEM; ESTIMATED PARAMETER; LOW SENSITIVITY; MAXIMUM A POSTERIORI ESTIMATION; MORPHOLINES; MULTISTEP REACTIONS; NETWORK PARAMETERS; NUCLEOPHILIC AROMATIC SUBSTITUTION; ON-LINE ANALYSIS; PARAMETER UNCERTAINTY; PRODUCT FORMATION; PRODUCT YIELDS; RATE PARAMETERS; REACTION NETWORK; SERIES-PARALLEL;

CHEMICAL ANALYSIS; DESIGN OF EXPERIMENTS; KINETIC PARAMETERS; MAXIMUM LIKELIHOOD ESTIMATION; ONLINE SYSTEMS; OPTIMIZATION; REACTION KINETICS;

AUTOMATION;

EID: 84869413753     PISSN: 10836160     EISSN: 1520586X     Source Type: Journal    
DOI: 10.1021/op3001838     Document Type: Article

References (32)

1. Hartman, R. L.; McMullen, J. P.; Jensen, K. E. Angew. Chem., Int. Ed. 2011, 50, 7502-7519
2. Webb, D.; Jamison, T. F. Chem. Sci. 2010, 1, 675-680
3. Wiles, C.; Watts, P. Green Chem. 2012, 14, 38-54
4. Geyer, K.; Gustafsson, T.; Seeberger, P. H. Synlett 2009, 2382-2391
5. Hartman, R. L.; Jensen, K. F. Lab Chip 2009, 9, 2495-2507
6. Bedore, M. W.; Zaborenko, N.; Jensen, K. F.; Jamison, T. F. Org. Process Res. Dev. 2010, 14, 432-440
7. Muller, G.; Gaupp, T.; Wahl, F.; Wille, G. Chimia 2006, 60, 618-622
8. Watts, P.; Haswell, S. J. Chem. Soc. Rev. 2005, 34, 235-246
9. McMullen, J. P.; Jensen, K. F., Annu. Rev. Anal. Chem., Vol. 3 2010, 3) 19-42.
10. Goodell, J. R.; McMullen, J. P.; Zaborenko, N.; Maloney, J. R.; Ho, C. X.; Jensen, K. F.; Porco, J. A.; Beeler, A. B. J. Org. Chem. 2009, 74, 6169-6180
11. McMullen, J. P.; Jensen, K. F. Org. Process Res. Dev. 2010, 14, 1169-1176
12. McMullen, J. P.; Stone, M. T.; Buchwald, S. L.; Jensen, K. F. Angew. Chem., Int. Ed. 2010, 49, 7076-80
13. McMullen, J. P.; Jensen, K. F. Org. Process Res. Dev. 2011, 15, 398-407
14. Zhang, Q.; Liu, Y.; Gao, F.; Ding, Q.; Cho, C.; Hur, W.; Jin, Y. H.; Uno, T.; Joazeiro, C. A. P.; Gray, N. J. Am. Chem. Soc. 2006, 128, 2182-2183
15. Anderson, M.; Beattie, J. F.; Breault, G. A.; Breed, J.; Byth, K. F.; Culshaw, J. D.; Ellston, R. P. A.; Green, S.; Minshull, C. A.; Norman, R. A.; Pauptit, R. A.; Stanway, J.; Thomas, A. P.; Jewsbury, P. J. Bioorg. Med. Chem. Lett. 2003, 13, 3021-3026
16. Cumming, J. G.; McKenzie, C. L.; Bowden, S. G.; Campbell, D.; Masters, D. J.; Breed, J.; Jewsbury, P. J. Bioorg. Med. Chem. Lett. 2004, 14, 5389-5394
17. Tavares, F. X.; Boucheron, J. A.; Dickerson, S. H.; Griffin, R. J.; Preugschat, F.; Thomson, S. A.; Wang, T. Y.; Zhou, H. Q. J. Med. Chem. 2004, 47, 4716-4730
18. Wang, S. D.; Meades, C.; Wood, G.; Osnowski, A.; Anderson, S.; Yuill, R.; Thomas, M.; Mezna, M.; Jackson, W.; Midgley, C.; Griffiths, G.; Fleming, I.; Green, S.; McNae, I.; Wu, S. Y.; McInnes, C.; Zheleva, D.; Walkinshaw, M. D.; Fischer, P. M. J. Med. Chem. 2004, 47, 1662-1675
19. Zagulyaeva, O. A.; Bukhatkina, N. V.; Mamaev, V. P. Zh. Org. Khim. 1978, 14, 409-413
20. Liu, M.; Wang, S. Y.; Clampit, J. E.; Gum, R. J.; Haasch, D. L.; Rondinone, C. M.; Trevillyan, J. M.; Abad-Zapatero, C.; Fry, E. H.; Sham, H. L.; Liu, G. Bioorg. Med. Chem. Lett. 2007, 17, 668-672
21. Delcorona, L.; Signorelli, G.; Manzardo, S.; Pinzetta, A.; Coppi, G. Eur. J. Med. Chem. 1991, 26, 729-733
22. Melander, L. Arkiv Kemi 1950, 2, 211-295
23. Bunnett, J. F.; Zahler, R. E. Chem. Rev. 1951, 49, 273-412
24. Bunnett, J. F. Q. Rev. Chem. Soc. 1958, 12, 1-16
25. Levenspiel, O. Chemical Reaction Engineering, 3 rd ed.; Wiley: New York, 1999.
26. Nagy, K. D.; Shen, B.; Jamison, T. F.; Jensen, K. F. Org. Process Res. Dev. 2012, 16, 976-981
27. Beck, J. V.; Arnold, K. J. Parameter Estimation in Engineering and Science; Wiley: New York, 1977.
28. Steinfeld, J. I.; Francisco, J. S.; Hase, W. L. Chemical Kinetics and Dynamics, 2 nd ed.; Prentice Hall: Upper Saddle River, NJ, 1999.
29. Draper, N. R.; Smith, H. Applied Regression Analysis; Wiley: New York, 1981.
30. Box, G. E. P.; Draper, N. R. Biometrika 1965, 52, 355-365
31. Box, G. E. P.; Lucas, H. L. Biometrika 1959, 46, 77-90
32. Zaborenko, N.; Murphy, E. R.; Kralj, J. G.; Jensen, K. F. Ind. Eng. Chem. Res. 2010, 49, 4132-4139