Kinetic Profiling of Catalytic Organic Reactions as a Mechanistic Tool

Journal of the American Chemical Society

Volumn 137, Issue 34, 2015, Pages 10852-10866

  Blackmond, Donna G ^a  

^a SCRIPPS RESEARCH INSTITUTE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CATALYSIS; COMPLEX NETWORKS;

CATALYTIC NETWORKS; CATALYTIC REACTIONS; CONTINUOUS REACTIONS; KINETIC MEASUREMENT; MECHANISTIC ANALYSIS; ORGANIC REACTION; REACTION PROFILE; REACTION PROGRESS;

KINETICS;

ALCOHOL DERIVATIVE; ALDEHYDE DERIVATIVE; ALKENE DERIVATIVE; AMINE; BENZOPHENONE DERIVATIVE; CARBONYL DERIVATIVE; ELECTROPHILE; ENAMINE; EPOXIDE; GERANIOL; HEXYLAMINE; HYDRAZONE DERIVATIVE; ISOVALERALDEHYDE; NUCLEOPHILE; OXAZOLIDINONE DERIVATIVE; PALLADIUM; PIPERAZINE DERIVATIVE; QUINONE DERIVATIVE;

ACCELERATION; ALDOL REACTION; ALKYLATION; AMINATION; CALORIMETRY; CATALYSIS; CATALYST; CHEMICAL PARAMETERS; CHEMICAL REACTION; CHROMATOGRAPHY; CONCENTRATION (PARAMETERS); CONTROLLED STUDY; FOURIER TRANSFORM INFRARED PHOTOACOUSTIC SPECTROSCOPY; HYDROGENATION; ISOMERIZATION; KINETIC PARAMETERS; KINETICS; LOW TEMPERATURE; NEGATIVE FEEDBACK; NOISE; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; REACTION ANALYSIS; REACTION TIME; REVIEW; SUBSTRATE CONCENTRATION;

EID: 84940834557     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/jacs.5b05841     Document Type: Review

References (56)

1. Attribution goes to an anonymous reviewer for the "straight line" comment; I am indebted to Dave Collum for the "take-home message" concept I use in this review, which he uses to great advantage in his kinetics courses.
2. Blackmond, D. G. Angew. Chem., Int. Ed. 2005, 44, 4302 10.1002/anie.200462544
3. Mathew, J. S.; Klussmann, M.; Iwamura, H.; Valera, F.; Futran, A.; Emanuelsson, E. A. C.; Blackmond, D. G. J. Org. Chem. 2006, 71, 4711 10.1021/jo052409i
4. Zotova, N.; Iwamura, H.; Mathew, S. P.; Blackmond, D. G. In Trends in Process Chemistry; Braish, T.; Gadasamatti, K., Eds.; CRC Press: New York, 2008; p 455.
5. Shekhar, S.; Ryberg, P.; Hartwig, J. F.; Mathew, J. S.; Blackmond, D. G.; Strieter, E. R.; Buchwald, S. L. J. Am. Chem. Soc. 2006, 128, 3584 10.1021/ja045533c
6. Blackmond, D. G.; Schultz, T.; Mathew, J. S.; Loew, C.; Rosner, T.; Pfaltz, A. Synlett 2006, 18, 3135 10.1055/s-2006-951514
7. Rosner, T.; Le Bars, J.; Pfaltz, A.; Blackmond, D. G. J. Am. Chem. Soc. 2001, 123, 1848 10.1021/ja003191e
8. List, B.; Lerner, R. A.; Barbas, C. F., III. J. Am. Chem. Soc. 2000, 122, 2395 10.1021/ja994280y
9. Ahrendt, K. A.; Borths, C. J.; MacMillan, D. W. C. J. Am. Chem. Soc. 2000, 122, 4243 10.1021/ja000092s
10. MacMillan, D. W. C. Nature 2008, 455, 304 10.1038/nature07367
11. Brochu, M. P.; Brow, S. P.; MacMillan, D. W. C. J. Am. Chem. Soc. 2004, 126, 4108 10.1021/ja049562z
12. Burés, J.; Armstrong, A.; Blackmond, D. G. J. Am. Chem. Soc. 2012, 134, 14264 10.1021/ja307209v
13. Wiest, J., Masters' Thesis, University of Basel, 2012.
14. Zotova, N.; Broadbelt, L. J.; Armstrong, A.; Blackmond, D. G. Bioorg. Med. Chem. Lett. 2009, 19, 3934 10.1016/j.bmcl.2009.03.112
15. Zotova, N.; Franzke, A.; Armstrong, A.; Blackmond, D. G. J. Am. Chem. Soc. 2007, 129, 15100 10.1021/ja0738881
16. Burès, J.; Armstrong, A.; Blackmond, D. G. Angew. Chem., Int. Ed. 2014, 53, 8700 10.1002/anie.201404327
17. Tiecco, M.; Carlone, A.; Sternativo, S.; Marini, F.; Bartoli, G.; Melchiorre, P. Angew. Chem., Int. Ed. 2007, 46, 6882 10.1002/anie.200702318
18. Sunden, H.; Rios, R.; Cordova, A. Tetrahedron Lett. 2007, 48, 7865 10.1016/j.tetlet.2007.08.125
19. Hein, J. E.; Armstrong, A.; Blackmond, D. G. Org. Lett. 2011, 13, 4300 10.1021/ol201639z
20. Mathew, S. P.; Iwamura, H.; Blackmond, D. G. Angew. Chem., Int. Ed. 2004, 43, 3317 10.1002/anie.200453997
21. Mathew, S. P.; Klussmann, M.; Iwamura, H.; Wells, D. H., Jr.; Armstrong, A.; Blackmond, D. G. Chem. Commun. 2006, 4291 10.1039/b609926b
22. Zotova, N.; Moran, A.; Armstrong, A.; Blackmond, D. G. Adv. Synth. Catal. 2009, 351, 2765 10.1002/adsc.200900665
23. Engle, K. M.; Wang, D.-H.; Yu, J.-Q. J. Am. Chem. Soc. 2010, 132, 14137 10.1021/ja105044s
24. Baxter, R. D.; Sale, D.; Engle, K. M.; Yu, J.-Q.; Blackmond, D. G. J. Am. Chem. Soc. 2012, 134, 4600 10.1021/ja207634t
25. Kitamura, M.; Suga, S.; Oka, H.; Noyori, R. J. Am. Chem. Soc. 1998, 120, 9800 10.1021/ja981740z
26. Cornish-Bowden, A. Fundamentals of Enzyme Kinetics, 2nd ed.; Protland Press: London, 1995; Chpt. 4.
27. Tokunaga, M.; Larrow, J. F.; Kakiuchi, F.; Jacobsen, E. N. Science 1997, 277, 936 10.1126/science.277.5328.936
28. Nielsen, L. P. C.; Stevenson, C. P.; Blackmond, D. G.; Jacobsen, E. N. J. Am. Chem. Soc. 2004, 126, 1360 10.1021/ja038590z
29. Luchi, J.; Blackmond, D. G.; Jacobsen, E. N.; unpublished data.
30. Nielsen, L. P. C.; Zuend, S. J.; Ford, D. D.; Jacobsen, E. N. J. Org. Chem. 2012, 77, 2486 10.1021/jo300181f
31. Ferretti, A. C.; Mathew, J. S.; Ashworth, I.; Purdy, M.; Brennan, C.; Blackmond, D. G. Adv. Synth. Catal. 2008, 350, 1007 10.1002/adsc.200800006
32. Ferretti, A. C.; Mathew, J. S.; Blackmond, D. G. Ind. Eng. Chem. Res. 2007, 46, 8584 10.1021/ie070050d
33. Ferretti, A.; Brennan, C.; Blackmond, D.G. Inorg. Chim. Acta 2011, 369, 292 10.1016/j.ica.2011.01.018
34. Takaya, H.; Ohta, T.; Inoue, S.-I.; Tokunaga, M.; Kitamura, M.; Noyori, R. Org. Synth. 1993, 72, 74
35. Noyori, R.; Takaya, H. Acc. Chem. Res. 1990, 23, 345 10.1021/ar00178a005
36. Sun, Y.; LeBlond, C.; Wang, J.; Blackmond, D. G.; Laquidara, J.; Sowa, J. R., Jr. J. Am. Chem. Soc. 1995, 117, 12647 10.1021/ja00155a034
37. Sun, Y.; Wang, J.; LeBlond, C.; Reamer, R. A.; Laquidara, J.; Sowa, J. R.; Blackmond, D. G. J. Organomet. Chem. 1997, 548, 65 10.1016/S0022-328X(97)00165-4
38. Sun, Y.; Wang, J.; LeBlond, C.; Landau, R. N.; Laquidara, J.; Sowa, J. R.; Blackmond, D. G. J. Mol. Catal. A: Chem. 1997, 115, 495 10.1016/S1381-1169(96)00353-6
39. Soai, K.; Shibata, T.; Morioka, H.; Choji, K. Nature 1995, 378, 767 10.1038/378767a0
40. Gehring, T.; Quaranta, M.; Odell, B.; Blackmond, D. G.; Brown, J. M. Angew. Chem., Int. Ed. 2012, 51, 9539 10.1002/anie.201203398
41. Hein, J. E.; Gherase, D.; Blackmond, D. G. Top. Curr. Chem. 2013, 333, 83 10.1007/128-2012-397
42. Buono, F. G.; Blackmond, D. G. J. Am. Chem. Soc. 2003, 125, 8978-8979 10.1021/ja034705n
43. Quaranta, M.; Gehring, T.; Odell, B.; Brown, J. M.; Blackmond, D. G. J. Am. Chem. Soc. 2010, 132, 15104 10.1021/ja103204w
44. Frank, F. C. Biochim. Biophys. Acta 1953, 11, 459-463 10.1016/0006-3002(53)90082-1
45. Calvin, M. Molecular Evolution; Oxford University Press, Oxford, 1969.
46. Blackmond, D. G. Proc. Natl. Acad. Sci. U. S. A. 2004, 101, 5732-5736 10.1073/pnas.0308363101
47. Landau, R. N.; Singh, U. K.; Gortsema, F. P.; Sun, Y.; Gomolka, S. C.; Lam, T.; Futran, M.; Blackmond, D. G. J. Catal. 1995, 157, 201-208 10.1006/jcat.1995.1280
48. LeBlond, C.; Larsen, R.; Orella, C.; Forman, A.; Landau, R. N.; Laquidara, J.; Sowa, J. R.; Blackmond, D. G. Thermochim. Acta 1996, 289, 189 10.1016/S0040-6031(96)03072-9
49. Pye, P. J.; Rossen, K.; Reamer, R. A.; Tsou, N. N.; Volante, R. P.; Reider, P. J. J. Am. Chem. Soc. 1997, 119, 6207 10.1021/ja970654g
50. Kedia, S. B.; Mitchell, M. B. Org. Process Res. Dev. 2009, 13, 420 10.1021/op800205x
51. Yu, L. X. Pharm. Res. 2008, 25, 781 10.1007/s11095-007-9511-1
52. Mettler Autochem iC Kinetics software: http://us.mt.com/us/en/home/products/L1-AutochemProducts/AutoChem-software/iCKinetics.html; the software addresses the question of what constitutes a statistically accepatable "overlay" in graphical rate equations to determine reaction orders. A free on-demand webinar is also available from Mettler Autochem: http://www.pharmaceuticalonline.com/doc/webinar-reaction-progress-kinetic-analysis-0009.
53. Wikipedia page: https://en.wikipedia.org/wiki/Reaction-progress-kinetic-analysis.
54. Devery, J. J.; Conrad, J. C.; MacMillan, D. W. C.; Flowers, R. A., II Angew. Chem., Int. Ed. 2010, 49, 6106 10.1002/anie.201001673
55. Wagner, A. J.; Rychnovsky, S. D. Org. Lett. 2013, 15, 5504 10.1021/ol402643n
56. Scott, M.; Sud, A.; Boess, E.; Klussmann, M. J. Org. Chem. 2014, 79, 12033 10.1021/jo5018876