Mechanistic rationalization of unusual sigmoidal kinetic profiles in the machetti-de sarlo cycloaddition reaction

Journal of the American Chemical Society

Volumn 137, Issue 6, 2015, Pages 2386-2391

  Mower, Matthew P ^a   Blackmond, Donna G ^a  

^a SCRIPPS RESEARCH INSTITUTE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CYCLOADDITION;

1 ,3-DIPOLARCYCLOADDITION; BASE CATALYZED; CYCLOADDITION REACTION; INDUCTION PERIODS; KINETIC PROFILES; KINETIC STUDY; ORGANIC REACTION; SITU KINETICS;

KINETICS;

ACETAMIDE DERIVATIVE; ACRYLAMIDE; N METHYLNITROACETAMIDE; UNCLASSIFIED DRUG;

ARTICLE; CYCLOADDITION; KINETICS; MACHETTI DE SARLO CYCLOADDITION REACTION; PRECURSOR;

EID: 84923250076     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja512753v     Document Type: Article

References (43)

1. Blackmond, D. G. Angew. Chem., Int. Ed. 2005, 44, 4302
2. Mathew, J. S.; Klussmann, M.; Iwamura, H.; Valera, F.; Futran, A.; Emanuelsson, E. A. C.; Blackmond, D. G. J. Org. Chem. 2006, 71, 4711
3. Zuend, S. F.; Jacobsen, E. N. J. Am. Chem. Soc. 2009, 131, 15359
4. Rosner, T.; Le Bars, J.; Pfaltz, A.; Blackmond, D. G. J. Am. Chem. Soc. 2001, 123, 1848
5. Rosner, T.; Pfaltz, A.; Blackmond, D. G. J. Am. Chem. Soc. 2001, 123, 4621
6. 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, 3584-3591
7. Blackmond, D. G.; Schultz, T.; Mathew, J. S.; Loew, C.; Rosner, T.; Pfaltz, A. Synlett 2006, 18, 3135
8. Mathew, S. P.; Klussmann, M.; Iwamura, H.; Wells, D. H., Jr.; Armstrong, A.; Blackmond, D. G. Chem. Commun. 2006, 4291
9. Phua, P. H.; Mathew, S. P.; White, A. J. P.; de Vries, J. G.; Blackmond, D. G.; Hii, K. K. Chem.-Eur. J. 2007, 13, 4602
10. Blackmond, D. G. J. Am. Chem. Soc. 1997, 119, 12934
11. Blackmond, D. G. Acc. Chem. Res. 2000, 33, 402
12. von Kiedrowski, G. Angew. Chem., Int. Ed. Engl. 1986, 25, 932-935
13. Chen, J.; Körner, S.; Craig, S. L.; Lin, S.; Rudkevich, D. M.; Rebek, J., Jr. Proc. Natl. Acad. Sci., U.S.A. 2002, 99, 2593-2596
14. Sadownik, J. W.; Philp, D. Angew. Chem., Int. Ed. 2008, 51, 9965-9970
15. Blow, N. Nat. Methods 2007, 4, 869-875
16. Saiki, R. K.; Bugawan, T. L.; Horn, G. T.; Mullis, K. B.; Erlich, H. A. Nature 1986, 324, 163-166
17. Yoon, H. J.; Mirkin, C. A. J. Am. Chem. Soc. 2008, 130, 11590-11591
18. Soai, K.; Shibata, T.; Morioka, H.; Choji, K. Nature 1995, 378, 767
19. Kawasaki, T.; Matsumura, Y.; Tsutsumi, T.; Suzuki, K.; Ito, M.; Soai, K. Science 2009, 324, 492
20. Soai, K.; Kawasaki, T. Chem. Today 2009, 27, 3
21. Blackmond, D. G.; McMillan, C. R.; Ramdeehul, S.; Schorm, A.; Brown, J. M. J. Am. Chem. Soc. 2001, 123, 10103
22. Buono, F. G.; Blackmond, D. G. J. Am. Chem. Soc. 2003, 125, 8978
23. Quaranta, M.; Gehring, T.; Odell, B.; Brown, J. M.; Blackmond, D. G. J. Am. Chem. Soc. 2010, 132, 15104
24. Watzky, M. A.; Finke, R. G. J. Am. Chem. Soc. 1997, 119, 10382-10400
25. Besson, C.; Finney, E. E.; Finke, R. G. J. Am. Chem. Soc. 2005, 127, 8179-8184
26. Mondloch, J. E.; Bayram, E.; Finke, R. G. J. Mol. Catal. A 2012, 355, 1-38
27. Wang, F.; Richards, V. N.; Shields, S. P.; Buhro, W. E. Chem. Mater. 2014, 26, 5-21
28. Morris, A. M.; Watzky, M. A.; Agar, J. N.; Finke, R. G. Biochemistry 2008, 47, 2413-2427
29. Blackmond, D. G. Angew. Chem., Int. Ed. 2009, 48, 386-390
30. Cecchi, L.; De Sarlo, F.; Machetti, F. Tetrahedron Lett. 2005, 46, 7877
31. Cecchi, L.; De Sarlo, F.; Machetti, F. Eur. J. Org. Chem. 2006, 4852
32. Machetti, F.; Cecchi, L.; Trogu, E.; De Sarlo, F. Eur. J. Org. Chem. 2007, 4352
33. Guideri, L.; De Sarlo, F.; Machetti, F. Chem.-Eur. J. 2013, 19, 665
34. De Sarlo, F.; Machetti, F. In Methods and Apllications of Cycloaddition Reactions in Organic Synthesis, 1 st ed.; Nishiwaki, N., Ed.; John Wiley & Sons, Inc.: New York, 2014; pp 205-222.
35. Biagiotti, G.; Cicchi, S.; De Sarlo, F.; Machetti, F. Eur. J. Org. Chem. 2014, 7906-7915
36. Trogu, E.; Vinattieri, C.; De Sarlo, F.; Machetti, F. Chem.-Eur. J. 2012, 18, 2081
37. Benson, S. W. J. Chem. Phys. 1956, 20, 1605-1612
38. Hein, J. E.; Cao, B. H.; Viedma, C.; Kellogg, R. M.; Blackmond, D. G. J. Am. Chem. Soc. 2012, 134, 12629
39. Spokes, G. N.; Benson, S. W. J. Am. Chem. Soc. 1967, 89, 6030
40. Khrapkovskii, G. M.; Shamov, A. G.; Nikolaeva, E. V.; Chachkov, D. V. Russ. Chem. Rev. 2009, 78, 903
41. Pascal, R.; Taillades, J.; Commeyras, A. Tetrahedron 1978, 34, 2275
42. Matt, C.; Wagner, A.; Mioskowski, C. J. Org. Chem. 1997, 62, 234
43. Clayden, J.; Greeves, N.; Warren, S.; Wothers, P. Organic Chemistry; Oxford University Press: Oxford, 2001; p 934.