Nucleophilic reactivities of deoxy breslow intermediates: How does aromaticity affect the catalytic activities of N-heterocyclic carbenes?

Angewandte Chemie - International Edition

Volumn 51, Issue 25, 2012, Pages 6231-6235

  Maji, Biplab ^a   Horn, Markus ^a   Mayr, Herbert ^a  

^a UNIVERSITY OF MUNICH   (Germany)

Author keywords

azolium ions; kinetics; Lewis basicity; linear free energy relationships; umpolung

Indexed keywords

AROMATICITIES; KINETIC INVESTIGATIONS; LEWIS BASICITY; LINEAR FREE ENERGY RELATIONSHIPS; N-HETEROCYCLIC CARBENES; NUCLEOPHILIC REACTIVITY; UMPOLUNG;

CATALYSIS; CHEMISTRY; ENZYME KINETICS;

ORGANIC COMPOUNDS;

EID: 84862703524     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201202327     Document Type: Article

References (81)

1. First isolation:, A. J. Arduengo III, R. L. Harlow, M. Kline, J. Am. Chem. Soc. 1991, 113, 361-363
2. For physicochemical data of NHCs see:, T. Dröge, F. Glorius, Angew. Chem. 2010, 122, 7094-7107
3. Angew. Chem. Int. Ed. 2010, 49, 6940-6952.
4. D. Seebach, Angew. Chem. 1979, 91, 259-278
5. Angew. Chem. Int. Ed. Engl. 1979, 18, 239-258
6. X. Bugaut, F. Glorius, Chem. Soc. Rev. 2012, 41, 3511-3522.
7. D. Enders, O. Niemeier, A. Henseler, Chem. Rev. 2007, 107, 5606-5655
8. N. Marion, S. Díez-González, S. P. Nolan, Angew. Chem. 2007, 119, 3046-3058
9. Angew. Chem. Int. Ed. 2007, 46, 2988-3000
10. V. Nair, S. Vellalath, B. P. Babu, Chem. Soc. Rev. 2008, 37, 2691-2698
11. P.-C. Chiang, J. W. Bode, in N-Heterocyclic Carbenes: From Laboratory Curiosities to Efficient Synthetic Tools (Ed.:, S. S. Díez- González,), Royal Society of Chemistry, Cambridge, 2010, pp. 399-435
12. K. Zeitler, Angew. Chem. 2005, 117, 7674-7678
13. Angew. Chem. Int. Ed. 2005, 44, 7506-7510
14. J. L. Moore, T. Rovis, Top. Curr. Chem. 2010, 291, 77
15. V. Nair, R. S. Menon, A. T. Biju, C. R. Sinu, R. R. Paul, A. Jose, V. Sreekumar, Chem. Soc. Rev. 2011, 40, 5336-5346
16. A. T. Biju, N. Kuhl, F. Glorius, Acc. Chem. Res. 2011, 44, 1182-1195.
17. T. Ukai, R. Tanaka, T. Dokawa, J. Pharm. Soc. Jpn. 1943, 63, 296-300
18. For an excellent review of asymmetric benzoin condensations (from 1966 to 2003) see:, D. Enders, T. Balensiefer, Acc. Chem. Res. 2004, 37, 534-541.
19. H. Stetter, Angew. Chem. 1976, 88, 695-704
20. Angew. Chem. Int. Ed. Engl. 1976, 15, 639-647.
21. R. Breslow, J. Am. Chem. Soc. 1958, 80, 3719-3726.
22. C. Fischer, S. W. Smith, D. A. Powell, G. C. Fu, J. Am. Chem. Soc. 2006, 128, 1472-1473
23. S. Matsuoka, Y. Ota, A. Washio, A. Katada, K. Ichioka, K. Takagi, M. Suzuki, Org. Lett. 2011, 13, 3722-3725
24. A. T. Biju, M. Padmanaban, N. E. Wurz, F. Glorius, Angew. Chem. 2011, 123, 8562-8565
25. Angew. Chem. Int. Ed. 2011, 50, 8412-8415
26. R. L. Atienza, H. S. Roth, K. A. Scheidt, Chem. Sci. 2011, 2, 1772-1776
27. Y. Zhang, E. Y. X. Chen, Angew. Chem. 2012, 124, 2515-2519
28. Angew. Chem. Int. Ed. 2012, 51, 2465-2469.
29. C. E. I. Knappke, A. J. Arduengo III, H. Jiao, J.-M. Neudörfl, A. J. von Wangelin, Synthesis 2011, 3784-3795.
30. B. Maji, M. Breugst, H. Mayr, Angew. Chem. 2011, 123, 7047-7052
31. Angew. Chem. Int. Ed. 2011, 50, 6915-6919.
32. A. Berkessel, S. Elfert, K. Etzenbach-Effers, J. H. Teles, Angew. Chem. 2010, 122, 7275-7279
33. Angew. Chem. Int. Ed. 2010, 49, 7120-7124
34. R. Breslow, R. Kim, Tetrahedron Lett. 1994, 35, 699-702
35. Y.-T. Chen, G. L. Barletta, K. Haghjoo, J. T. Cheng, F. Jordan, J. Org. Chem. 1994, 59, 7714-7722
36. M. J. White, F. J. Leeper, J. Org. Chem. 2001, 66, 5124-5131
37. W. Schrader, P. P. Handayani, C. Burstein, F. Glorius, Chem. Commun. 2007, 716-718
38. J. H. Teles, J.-P. Melder, K. Ebel, R. Schneider, E. Gehrer, W. Harder, S. Bode, D. Enders, K. Breuer, G. Raabe, Helv. Chim. Acta 1996, 79, 61-83
39. F. Jordan, Z. H. Kudzin, C. B. Rios, J. Am. Chem. Soc. 1987, 109, 4415-4416
40. L. Pignataro, T. Papalia, A. M. Z. Slawin, S. M. Goldup, Org. Lett. 2009, 11, 1643-1646
41. D. A. DiRocco, K. M. Oberg, T. Rovis, J. Am. Chem. Soc. 2012, 134, 6143-6145.
42. N. Kuhn, H. Bohnen, J. Kreutzberg, D. Bläser, R. Boese, J. Chem. Soc. Chem. Commun. 1993, 1136-1137
43. A. J. Arduengo III, F. Davidson, H. V. R. Dias, J. R. Goerlich, D. Khasnis, W. J. Marshall, T. K. Prakasha, J. Am. Chem. Soc. 1997, 119, 12742-12749
44. O. Kaufhold, F. E. Hahn, Angew. Chem. 2008, 120, 4122-4126
45. Angew. Chem. Int. Ed. 2008, 47, 4057-4061
46. A. Fürstner, M. Alcarazo, R. Goddard, C. W. Lehmann, Angew. Chem. 2008, 120, 3254-3258
47. Angew. Chem. Int. Ed. 2008, 47, 3210-3214
48. K.-P. Hartmann, M. Heuschmann, Angew. Chem. 1989, 101, 1288-1290
49. Angew. Chem. Int. Ed. Engl. 1989, 28, 1267-1268
50. M. Ernd, M. Heuschmann, H. Zipse, Helv. Chim. Acta 2005, 88, 1491-1518
51. H. Quast, M. Ach, M. K. Kindermann, P. Rademacher, M. Schindler, Chem. Ber. 1993, 126, 503-516
52. H. Quast, M. Ach, J. Balthasar, T. Hergenröther, D. Regnat, J. Lehmann, K. Banert, Helv. Chim. Acta 2005, 88, 1589-1609
53. C. E. I. Knappke, J.-M. Neudörfl, A. J. von Wangelin, Org. Biomol. Chem. 2010, 8, 1695-1705
54. D. Enders, K. Breuer, J. Runsink, J. H. Teles, Liebigs Ann. 1996, 2019-2028.
55. H. Mayr, T. Bug, M. F. Gotta, N. Hering, B. Irrgang, B. Janker, B. Kempf, R. Loos, A. R. Ofial, G. Remennikov, H. Schimmel, J. Am. Chem. Soc. 2001, 123, 9500-9512
56. R. Lucius, R. Loos, H. Mayr, Angew. Chem. 2002, 114, 97-102
57. Angew. Chem. Int. Ed. 2002, 41, 91-95
58. H. Mayr, B. Kempf, A. R. Ofial, Acc. Chem. Res. 2003, 36, 66-77
59. H. Mayr, A. R. Ofial, Pure Appl. Chem. 2005, 77, 1807-1821
60. H. Mayr, Angew. Chem. 2011, 123, 3692-3698
61. Angew. Chem. Int. Ed. 2011, 50, 3612-3618.
62. Gaussian 09, Revision A.02, M. J. Frisch et al., Gaussian, Inc., Wallingford CT, 2009.
63. P. v. R. Schleyer, C. Maerker, A. Dransfeld, H. Jiao, N. J. R. van E. Hommes, J. Am. Chem. Soc. 1996, 118, 6317-6318
64. P. v. R. Schleyer, M. Manoharan, Z. X. Wang, B. Kiran, H. Jiao, R. Puchta, N. J. R. van E. Hommes, Org. Lett. 2001, 3, 2465-2468
65. Z. Chen, C. S. Wannere, C. Corminboeuf, R. Puchta, P. v. R. Schleyer, Chem. Rev. 2005, 105, 3842-3888
66. P. v. R. Schleyer, in Chemical Reactivity Theory (Ed.:, P. K. Chattaraj,), Taylor & Francis/CRC Press, Boca Raton, 2009, pp. 419-438
67. J. A. N. F. Gomes, R. B. Mallion, Chem. Rev. 2001, 101, 1349-1383
68. G. Merino, T. Heine, G. Seifert, Chem. Eur. J. 2004, 10, 4367-4371.
69. R. A. Kunetskiy, S. M. Polyakova, J. VavÅík, I. CísaÅová, J. Saame, E. R. Nerut, I. Koppel, I. A. Koppel, A. Kütt, I. Leito, I. M. Lyapkalo, Chem. Eur. J. 2012, 18, 3621-3630.
70. H. Fallah-Bagher-Shaidaei, C. S. Wannere, C. Corminboeuf, R. Puchta, P. v. R. Schleyer, Org. Lett. 2006, 8, 863-866
71. J. Wu, P. v. R. Schleyer, personal communication.
72. S. Díez-González, N. Marion, S. P. Nolan, Chem. Rev. 2009, 109, 3612-3676
73. N-Heterocyclic Carbenes in Synthesis (Ed.:, S. P. Nolan,), Wiley-VCH, Weinheim, 2006
74. V. César, S. Bellemin-Laponnaz, L. H. Gade, Chem. Soc. Rev. 2004, 33, 619-636
75. S. Würtz, F. Glorius, Acc. Chem. Res. 2008, 41, 1523-1533
76. F. E. Hahn, M. C. Jahnke, Angew. Chem. 2008, 120, 3166-3216
77. Angew. Chem. Int. Ed. 2008, 47, 3122-3172
78. G. C. Vougioukalakis, R. H. Grubbs, Chem. Rev. 2010, 110, 1746-1787
79. M. J. Fuchter, Chem. Eur. J. 2010, 16, 12286-12294
80. K. Lee, A. R. Zhugralin, A. H. Hoveyda, J. Am. Chem. Soc. 2009, 131, 7253-7255
81. J. M. O'Brien, A. H. Hoveyda, J. Am. Chem. Soc. 2011, 133, 7712-7715.