A mechanistic study of the Lewis base-directed cycloaddition of 2-pyrones and alkynylboranes

Journal of the American Chemical Society

Volumn 136, Issue 24, 2014, Pages 8642-8653

  Crépin, Damien F P ^a   Harrity, Joseph P A ^a   Jiang, Julong ^a   Meijer, Anthony J H M ^a   Nassoy, Anne Chloé M A ^a   Raubo, Piotr ^b  

^a UNIVERSITY OF SHEFFIELD   (United Kingdom)

^b ASTRAZENECA   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

SYNTHESIS (CHEMICAL);

BASIC GROUPS; DENSITY FUNCTIONAL THEORY METHODS; DIELS-ALDER REACTION; FUNCTIONALIZED; LEWIS ACID; MECHANISTIC STUDIES; RATE ENHANCEMENT; REGIOCONTROL;

CHEMISTRY;

2 PYRONE DERIVATIVE; ALKADIENE; ALKYNYLBORANE; ALKYNYLTRIFLUOROBORATE DERIVATIVE; AROMATIC COMPOUND; BORANE DERIVATIVE; LEWIS ACID; LEWIS BASE; UNCLASSIFIED DRUG; 2-PYRONE; ALKYNE; PYRONE DERIVATIVE;

ARTICLE; CHEMICAL STRUCTURE; CRYSTAL STRUCTURE; CYCLOADDITION; DENSITY FUNCTIONAL THEORY; DIELS ALDER REACTION; ENTHALPY; CHEMISTRY; CYCLIZATION; QUANTUM THEORY;

ALKYNES; BORANES; CYCLIZATION; LEWIS BASES; MOLECULAR STRUCTURE; PYRONES; QUANTUM THEORY;

EID: 84902668746     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja501805r     Document Type: Article

References (46)

1. Woodard, B. T.; Posner, G. H. Adv. Cycloaddit. 1999, 5, 47
2. Diels, O.; Alder, K. Ann. Chem. 1931, 490, 257
3. Afarinkia, K.; Vinader, V.; Nelson, T. D.; Posner, G. H. Tetrahedron 1992, 48, 9111
4. Delaney, P. M.; Moore, J. E. Chem. Commun. 2006, 3323
5. Delaney, P. M.; Browne, D. L.; Adams, H.; Plant, A.; Harrity, J. P. A. Tetrahedron 2008, 64, 866
6. Evnin, A.; Seyferth, D. J. Org. Chem. 1967, 32, 952
7. Seyferth, D.; White, D. J. Organomet. Chem. 1972, 34, 119
8. Kranjc, K.; Štefane, B.; Polanc, S.; Kočevar, M. J. Org. Chem. 2004, 69, 3190
9. Vivat, J. F.; Adams, H.; Harrity, J. P. A. Org. Lett. 2010, 12, 160
10. Kirkham, J. D.; Butlin, R. J.; Harrity, J. P. A. Angew. Chem., Int. Ed. 2012, 51, 6402
11. Singleton, D. A.; Martinez, J. P. J. Am. Chem. Soc. 1990, 112, 7423
12. Singleton, D. A. J. Am. Chem. Soc. 1992, 114, 6563
13. Leung, S.-W.; Singleton, D. A. J. Org. Chem. 1992, 57, 4796
14. Leung, S.-W.; Singleton, D. A. J. Org. Chem. 1997, 62, 1955
15. Sakata, K.; Fujimoto, H. J. Org. Chem. 2013, 78, 3095
16. Pham, H. V.; Paton, R. S.; Ross, A. G.; Danishefsky, S. J.; Houk, K. N. J. Am. Chem. Soc. 2014, 136, 2397
17. Birney, D. M.; Houk, K. N. J. Am. Chem. Soc. 1990, 112, 4127
18. Domingo, L. R.; Arnó, M.; Sáez, J. A. J. Org. Chem. 2009, 74, 5934
19. Domingo, L. R. Org. Chem.: Curr. Res. 2013, 2, 120
20. Soto-Delgado, J.; Saez, J. A.; Tapia, R. A.; Domingo, L. R. Org. Biomol. Chem. 2013, 11, 8357
21. Arno, M.; Picher, M. T.; Domingo, L. R.; Andres, J. Chem.-Eur. J. 2004, 10, 4742
22. Sarotti, A. M. Org. Biomol. Chem. 2014, 12, 187 and references therein
23. Becke, A. D. Phys. Rev. A 1988, 38, 3098
24. Becke, A. D. J. Chem. Phys. 1993, 98, 1372
25. Lee, C.; Yang, W.; Parr, R. G. Phys. Rev. B 1988, 37, 785
26. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Scalmani, G.; Barone, V.; Mennucci, B.; Petersson, G. A.; Nakatsuji, H.; Caricato, M.; Li, X.; Hratchian, H. P.; Izmaylov, A. F.; Bloino, J.; Zheng, G.; Sonnenberg, J. L.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Vreven, T.; Montgomery, J. A., Jr.; Peralta, J. E.; Ogliaro, F.; Bearpark, M.; Heyd, J. J.; Brothers, E.; Kudin, K. N.; Staroverov, V. N.; Kobayashi, R.; Normand, J.; Raghavachari, K.; Rendell, A.; Burant, J. C.; Iyengar, S. S.; Tomasi, J.; Cossi, M.; Rega, N.; Millam, J. M.; Klene, M.; Knox, J. E.; Cross, J. B.; Bakken, V.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R. E.; Yazyev, O.; Austin, A. J.; Cammi, R.; Pomelli, C.; Ochterski, J. W.; Martin, R. L.; Morokuma, K.; Zakrzewski, V. G.; Voth, G. A.; Salvador, P.; Dannenberg, J. J.; Dapprich, S.; Daniels, A. D.; Farkas, Ö.; Foresman, J. B.; Ortiz, J. V.; Cioslowski, J.; Fox, D. J. Gaussian 09, revision D.01; Gaussian, Inc.: Wallingford, CT, 2009.
27. Peng, C.; Schlegel, H. B. Isr. J. Chem. 1993, 33, 449
28. Peng, C.; Ayala, P. Y.; Schlegel, H. B.; Frisch, M. J. J. Comput. Chem. 1996, 17, 49
29. Cances, M. T.; Mennucci, B.; Tomasi, J. J. Chem. Phys. 1997, 107, 3032
30. Schlegel, H. B. J. Comput. Chem. 1982, 3, 214
31. Fukui, K. Acc. Chem. Res. 1981, 14, 363
32. Mennucci, B.; Tomasi, J. J. Chem. Phys. 1997, 106, 5151
33. Cossi, M.; Barone, V.; Mennucci, B.; Tomasi, J. Chem. Phys. Lett. 1998, 286, 253
34. Cossi, M.; Scalmani, G.; Rega, N.; Barone, V. J. Chem. Phys. 2002, 117, 43
35. Sing, U. C.; Kollman, P. A. J. Comput. Chem. 1984, 5, 129
36. Besler, B. H.; Merz, K. M.; Kollman, P. A. J. Comput. Chem. 1990, 11, 217
37. Bardin, V. V.; Adonin, N. Y.; Frohn, H.-J. J. Fluorine Chem. 2007, 128, 699
38. Negishi, E.-i.; Idacavage, M. J.; Chiu, K.-W.; Yoshida, T.; Abramovitch, A.; Goettel, M. E.; Silveira, A.; Bretherick, H. D. J. Chem. Soc., Perkin Trans. 2 1978, 1225
39. Cao, Y.; Osuna, S.; Liang, Y.; Haddon, R. C.; Houk, K. N.; Braunschweig, A. B. J. Am. Chem. Soc. 2013, 135, 9240
40. Štefane, B.; Perdih, A.; Pevec, A.; Šolmajer, T.; Kočevar, M. Eur. J. Org. Chem. 2010, 5870
41. Kranjc, K.; Kočevar, M. New J. Chem. 2005, 29, 1027
42. Kozuch, S.; Shaik, S. Acc. Chem. Res. 2011, 44, 101
43. Kozuch, S.; Martin, J. M. L. ChemPhysChem 2011, 12, 1413
44. Kozuch, S. Wiley Interdiscip. Rev.: Comput. Mol. Sci. 2012, 2, 795
45. Kirkham, J. D.; Leach, A. G.; Row, E. C.; Harrity, J. P. A. Synthesis 2012, 44, 1964
46. Bayer, M. J.; Pritzkow, H.; Siebert, W. Eur. J. Org. Chem. 2002, 2069