Electrophilic aromatic substitutions of aryltrifluoroborates with retention of the BF3- group: Quantification of the activating and directing effects of the trifluoroborate group

Journal of the American Chemical Society

Volumn 135, Issue 16, 2013, Pages 6317-6324

  Berionni, Guillaume ^a   Morozova, Varvara ^a   Heininger, Maximilian ^a   Mayer, Peter ^a   Knochel, Paul ^a   Mayr, Herbert ^a  

^a UNIVERSITY OF MUNICH   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

ELECTROPHILIC AROMATIC SUBSTITUTIONS; ELECTROPHILIC SUBSTITUTIONS; IMINIUM; IMINIUM IONS; KINETICS AND MECHANISM; SINGLE CRYSTAL X-RAY ANALYSIS; THIENYL;

CHEMISTRY; SYNTHESIS (CHEMICAL);

X RAY ANALYSIS;

AMMONIA; BORIC ACID; BORON; ELECTROPHILE; IMINIUM ION; TRANSITION ELEMENT; TRIFLUOROBORATE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CRYSTAL STRUCTURE; ELECTROPHILICITY; KINETICS; SUBSTITUTION REACTION; X RAY ANALYSIS;

EID: 84876716300     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja4017655     Document Type: Article

References (87)

1. Darses, S.; Genet, J.-P. Chem. Rev. 2008, 108, 288
2. Molander, G. A.; Ellis, N. Acc. Chem. Res. 2007, 40, 275
3. Stefani, H. A.; Cella, R.; Vieira, A. S. Tetrahedron 2007, 63, 3623
4. Darses, S.; Genet, J.-P. Eur. J. Org. Chem. 2003, 4313
5. Hall, D. G. in Boronic Acids: Preparation and Applications in Organic Synthesis, Medicine and Materials, 2 nd ed.; Wiley-VCH: Weinheim, Germany, 2011.
6. Yamamoto, Y. Heterocycles 2012, 85, 799
7. Bonin, H.; Delacroix, T.; Gras, E. Org. Biomol. Chem. 2011, 9, 4714
8. Ishikura, M. Heterocycles 2011, 83, 247
9. Lennox, A. J. J.; Lloyd-Jones, G. C. Isr. J. Chem. 2010, 50, 664
10. Gillis, E. P.; Burke, M. D. Aldrichimica Acta 2009, 42, 17
11. Hayashi, T.; Yamasaki, K. Chem. Rev. 2003, 103, 2829
12. Fagnou, K.; Lautens, M. Chem. Rev. 2003, 103, 169
13. Molander, G. A.; Cavalcanti, L. N. J. Org. Chem. 2011, 76, 7195
14. Akula, M. R.; Yao, M.-L.; Kabalka, G. W. Tetrahedron Lett. 2010, 51, 1170
15. Yao, M.-L.; Reddy, M. S.; Yong, L.; Walfish, I.; Blevins, D. W.; Kabalka, G. W. Org. Lett. 2010, 12, 700
16. Cazorla, C.; Métay, E.; Andrioletti, B.; Lemaire, M. Tetrahedron Lett. 2009, 50, 3936
17. Kabalka, G. W.; Mereddy, A. R. Tetrahedron Lett. 2004, 45, 343
18. Molander, G. A.; Cavalcanti, L. N. J. Org. Chem. 2012, 77, 4402
19. Prakash, G. K. S.; Panja, C.; Mathew, T.; Surampudi, V.; Petasis, N. A.; Olah, G. A. Org. Lett. 2004, 6, 2205
20. Kerverdo, S.; Gingras, M. Tetrahedron Lett. 2000, 41, 6053
21. Wu, H.; Radomkit, S.; O'Brien, J. M.; Hoveyda, A. H. J. Am. Chem. Soc. 2012, 134, 8277
22. Pubill-Ulldemolins, C.; Bonet, A.; Bo, C.; Gulyás, H.; Fernández, E. Chem.-Eur. J. 2012, 18, 1121
23. Lee, K.-S.; Zhugralin, A. R.; Hoveyda, A. H. J. Am. Chem. Soc. 2009, 131, 7253
24. Candeias, N. R.; Montalbano, F.; Cal, P. M. S. D.; Gois, P. M. P. Chem. Rev. 2010, 110, 6169
25. Vieira, A. S.; Ferreira, F. P.; Fiorante, P. F.; Guadagnin, R. C.; Stefani, H. A. Tetrahedron 2008, 64, 3306
26. Chiu, C.-W.; Gabbaï, F. P. J. Am. Chem. Soc. 2006, 128, 14248
27. Tremblay-Morin, J.-P.; Raeppel, S.; Gaudette, F. Tetrahedron Lett. 2004, 45, 3471
28. Harwood, L. M.; Currie, G. S.; Drew, M. G. B.; Luke, R. W. A. Chem. Commun. 1996, 1953
29. Clausen, D. J.; Floreancig, P. E. J. Org. Chem. 2012, 77, 6574
30. Vo, C.-V. T.; Mitchell, T. A.; Bode, J. W. J. Am. Chem. Soc. 2011, 133, 14082
31. Larouche-Gauthier, R.; Elford, T. G.; Aggarwal, V. K. J. Am. Chem. Soc. 2011, 133, 16794
32. Mitchell, T. A.; Bode, J. W. J. Am. Chem. Soc. 2009, 131, 18057
33. Kim, J.; Movassaghi, M. J. Am. Chem. Soc. 2011, 133, 14940
34. Lee, S.; MacMillan, D. W. C. J. Am. Chem. Soc. 2007, 129, 15438
35. Negishi, E.-i.; Abramovitch, A.; Merrill, R. E. J. Chem. Soc. Chem. Comm. 1975, 138
36. Ishikura, M.; Kato, H. Tetrahedron 2002, 58, 9827
37. Ishikura, M.; Agata, I.; Katagiri, N. J. Heterocycl. Chem. 1999, 36, 873
38. Ishikura, M.; Terashima, M. J. Heterocycl. Chem. 1994, 31, 977
39. Ishikura, M.; Kamada, M.; Oda, I.; Ohta, T.; Terashima, M. J. Heterocycl. Chem. 1987, 24, 377
40. Negishi, E.-i.; Merrill, R. E.; Abramovitch, A.; Campbell, D. P. Bull. Korean Chem. Soc. 1987, 8, 424
41. Levy, A. B. Tetrahedron Lett. 1979, 20, 4021
42. Marinelli, E. R.; Levy, A. B. Tetrahedron Lett. 1979, 20, 2313
43. Utimoto, K.; Okada, K.-I.; Nozaki, H. Tetrahedron Lett. 1975, 16, 4239
44. Negishi, E.-i.; Merrill, R. E. J. Chem. Soc. Chem. Comm. 1974, 860
45. Bartolucci, S.; Bartoccini, F.; Righi, M.; Piersanti, G. Org. Lett. 2012, 14, 600
46. Appukkuttan, P.; Dehaen, W.; Van der Eycken, E. Chem.-Eur. J. 2007, 13, 6452
47. Isaad, J.; El Achari, A. Tetrahedron 2011, 67, 4939
48. Olah, G. A.; Piteau, M.; Laali, K.; Rao, C. B.; Farooq, O. J. Org. Chem. 1990, 55, 46
49. Molander, G. A.; Ajayi, K. Org. Lett. 2012, 14, 4242
50. Molander, G. A.; Febo-Ayala, W.; Jean-Gérard, L. Org. Lett. 2009, 11, 3830
51. Molander, G. A.; Cooper, D. J. J. Org. Chem. 2008, 73, 3885
52. Molander, G. A.; Ham, J.; Canturk, B. Org. Lett. 2007, 9, 821
53. Molander, G. A.; Cooper, D. J. J. Org. Chem. 2007, 72, 3558
54. Molander, G. A.; Ellis, N. M. J. Org. Chem. 2006, 71, 7491
55. Molander, G. A.; Ham, J. Org. Lett. 2006, 8, 2767
56. Molander, G. A.; Petrillo, D. E. J. Am. Chem. Soc. 2006, 128, 9634
57. Lennox, A. J. J.; Lloyd-Jones, G. C. Angew. Chem., Int. Ed. 2012, 51, 9385
58. Berionni, G.; Maji, B.; Knochel, P.; Mayr, H. Chem. Sci. 2012, 3, 878
59. Mayr, H.; Ofial, A. R. Pure Appl. Chem. 2005, 77, 1807
60. Mayr, H.; Kempf, B.; Ofial, A. R. Acc. Chem. Res. 2003, 36, 66
61. Mayr, H.; Bug, T.; Gotta, M. F.; Hering, N.; Irrgang, B.; Janker, B.; Kempf, B.; Loos, R.; Ofial, A. R.; Remennikov, G.; Schimmel, H. J. Am. Chem. Soc. 2001, 123, 9500
62. Lakhdar, S.; Westermaier, M.; Terrier, F.; Goumont, R.; Boubaker, T.; Ofial, A. R.; Mayr, H. J. Org. Chem. 2006, 71, 9088
63. Mayr, H.; Ofial, A. R. Tetrahedron Lett. 1997, 38, 3503
64. N and E parameters and references to original literature: www.cup.uni-muenchen.de/oc/mayr/DBintro.html.
65. Berionni, G.; Mayer, P.; Mayr, H. Acta Crystallogr., Sect. E: Struct. Rep. Online 2012, 68, m551
66. Desiraju, G. R. Angew. Chem., Int. Ed. 2011, 50, 52
67. Mayr, H.; Ofial, A. R.; Würthwein, E.-U.; Aust, N. C. J. Am. Chem. Soc. 1997, 119, 12727
68. Herrlich, M.; Hampel, N.; Mayr, H. Org. Lett. 2001, 3, 1629
69. Herrlich, M.; Mayr, H.; Faust, R. Org. Lett. 2001, 3, 1633
70. Batsanov, A. S.; Hérault, D.; Howard, J. A. K.; Patrick, L. G. F.; Probert, M. R.; Whiting, A. Organometallics 2007, 26, 2414
71. Coghlan, S. W.; Giles, R. L.; Howard, J. A. K.; Patrick, L. G. F.; Probert, M. R.; Smith, G. E.; Whiting, A. J. Organomet. Chem. 2005, 690, 4784
72. Bresner, C.; Aldridge, S.; Fallis, I. A.; Jones, C.; Ooi, L.-L. Angew. Chem., Int. Ed. 2005, 44, 3606
73. Oishi, S.; Saito, S. Angew. Chem., Int. Ed. 2012, 51, 5395
74. Gott, A. L.; Piers, W. E.; Dutton, J. L.; McDonald, R.; Parvez, M. Organometallics 2011, 30, 4236
75. Georgiou, I.; Ilyashenko, G.; Whiting, A. Acc. Chem. Res. 2009, 42, 756
76. Restorp, P.; Berryman, O. B.; Sather, A. C.; Ajami, D.; Rebek, J. Chem. Commun. 2009, 5692
77. Sumerin, V.; Schulz, F.; Atsumi, M.; Wang, C.; Nieger, M.; Leskelä, M.; Repo, T.; Pyykkö, P.; Rieger, B. J. Am. Chem. Soc. 2008, 130, 14117
78. Zhu, L.; Shabbir, S. H.; Gray, M.; Lynch, V. M.; Sorey, S.; Anslyn, E. V. J. Am. Chem. Soc. 2006, 128, 1222
79. Lennox, A. J. J.; Lloyd-Jones, G. C. J. Am. Chem. Soc. 2012, 134, 7431
80. Ting, R.; Harwig, C. W.; Lo, J.; Li, Y.; Adam, M. J.; Ruth, T. J.; Perrin, D. M. J. Org. Chem. 2008, 73, 4662
81. Colombel, V.; Presset, M.; Oehlrich, D.; Rombouts, F.; Molander, G. A. Org. Lett. 2012, 14, 1680
82. Fleury-Brégeot, N.; Raushel, J.; Sandrock, D. L.; Dreher, S. D.; Molander, G. A. Chem.-Eur. J. 2012, 18, 9564
83. Molander, G. A.; Beaumard, F. Org. Lett. 2011, 13, 1242
84. Raushel, J.; Sandrock, D. L.; Josyula, K. V.; Pakyz, D.; Molander, G. A. J. Org. Chem. 2011, 76, 2762
85. Luisi, R.; Giovine, A.; Florio, S. Chem.-Eur. J. 2010, 16, 2683
86. Molander, G. A.; Cooper, D. J. J. Org. Chem. 2008, 73, 3885
87. Batey, R. A.; Quach, T. D. Tetrahedron Lett. 2001, 42, 9099