Ligand effects in the formation of tertiary carbanions from substituted tertiary aromatic amides

Chemistry - A European Journal

Volumn 17, Issue 29, 2011, Pages 8078-8084

  Campbell Smith, Alison ^a   Donnard, Morgan ^b   Haywood, Joanna ^a   McPartlin, Mary ^a   Vincent, Mark A ^b   Hillier, Ian H ^b   Clayden, Jonathan ^b   Wheatley, Andrew E H ^a  

^a UNIVERSITY OF CAMBRIDGE   (United Kingdom)

^b UNIVERSITY OF MANCHESTER   (United Kingdom)

Author keywords

directed metalation; Lewis bases; ligand effects; lithium; tertiary carbanions

Indexed keywords

ALIPHATIC GROUPS; AROMATIC AMIDES; AROMATIC SYSTEM; BENZAMIDES; BENZYLIC; DIGLYMES; IN-LINE; LEWIS BASE; LEWIS BASIS; LIGAND EFFECT; LIGAND EFFECTS; LITHIATION; METALATIONS; OXYGEN ATOM; SOLID-STATE STRUCTURES; TERTIARY CARBANIONS;

AMIDES; AROMATIC COMPOUNDS; DEPROTONATION; DIMERS; ETHERS; LIGANDS; LITHIUM; METAL IONS; MINERALOGY; SELF ASSEMBLY;

X RAY CRYSTALLOGRAPHY;

EID: 79959973350     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.201100240     Document Type: Article

References (62)

1. R. Maggi, M. Schlosser, J. Org. Chem. 1996, 61, 5430-5434
2. C. G. Hartung, V. Snieckus, in Modern Arene Chemistry (Ed.:, D. Astruc,), Wiley-VCH, Weinheim, 2002, pp. 330-367
3. J. Clayden, in Chemistry of Organolithium Compounds, Vol. 1 (Eds.:, Z. Rappoport, I. Marek,), Wiley, Chichester, 2004, pp. 495-646
4. M. C. Whisler, M. MacNeil, V. Snieckus, P. Beak, Angew. Chem. 2004, 116, 2256-2276
5. Angew. Chem. Int. Ed. 2004, 43, 2206-2225
6. T. Macklin, V. Snieckus, in Handbook of C-H Transformations: Applications in Organic Synthesis (Ed.:, G. Dyker,), Wiley-VCH, Weinheim, 2005, pp. 106-118
7. J. Clayden, C. C. Stimson, M. Keenan, Chem. Commun. 2006, 1393-1394
8. R. E. Miller, T. Rantanen, K. A. Ogilvie, U. Groth, V. Snieckus, Org. Lett. 2010, 12, 2198-2201.
9. J. Clayden, Organolithiums: Selectivity for Synthesis, Pergamon, Oxford, 2002.
10. V. Snieckus, Chem. Rev. 1990, 90, 879-933.
11. H. W. Gschwend, H. R. Rodriguez, Org. React. 1979, 26, 1-360.
12. R. D. Clark, A. Jahangir, Org. React. 1995, 47, 1-314.
13. W. Wang, V. Snieckus, J. Org. Chem. 1992, 57, 424-426
14. A. Kalinin, M. A. Reed, B. H. Norman, V. Snieckus, J. Org. Chem. 2003, 68, 5992-5999
15. X. Cai, V. Snieckus, Org. Lett. 2004, 6, 2293-2295
16. C. A. James, V. Snieckus, J. Org. Chem. 2009, 74, 4080-4093.
17. P. Beak, A. Tse, J. Hawkins, C. W. Chen, S. Mills, Tetrahedron 1983, 39, 1983-1989
18. J. J. Court, D. J. Hlasta, Tetrahedron Lett. 1996, 37, 1335-1338.
19. R. J. Mills, N. J. Taylor, V. Snieckus, J. Org. Chem. 1989, 54, 4372-4385
20. A. Ahmed, J. Clayden, M. Rowley, Tetrahedron Lett. 1998, 39, 6103-6106
21. J. Clayden, L. W. Lai, Tetrahedron Lett. 2001, 42, 3163-3166
22. J. Clayden, L. W. Lai, M. Helliwell, Tetrahedron 2004, 60, 4399-4412.
23. J. Clayden, R. P. Davies, M. A. Hendy, R. Snaith, A. E. H. Wheatley, Angew. Chem. 2001, 113, 1282-1285
24. Angew. Chem. Int. Ed. 2001, 40, 1238-1240.
25. A. Bond, J. Clayden, A. E. H. Wheatley, Acta Crystallogr. E 2001, 57, o 292 -o 294.
26. D. R. Armstrong, J. Clayden, R. Haigh, D. J. Linton, P. Schooler, A. E. H. Wheatley, Chem. Commun. 2003, 1694-1695.
27. D. R. Armstrong, S. R. Boss, J. Clayden, R. Haigh, B. A. Kirmani, D. J. Linton, P. Schooler, A. E. H. Wheatley, Angew. Chem. 2004, 116, 2187-2190
28. Angew. Chem. Int. Ed. 2004, 43, 2135-2138.
29. R. E. Mulvey, F. Mongin, M. Uchiyama, Y. Kondo, Angew. Chem. 2007, 119, 3876-3899
30. Angew. Chem. Int. Ed. 2007, 46, 3802-3824.
31. W. Clegg, S. H. Dale, R. W. Harrington, E. Hevia, G. W. Honeyman, R. E. Mulvey, Angew. Chem. 2006, 118, 2434-2437
32. Angew. Chem. Int. Ed. 2006, 45, 2374-2377
33. Y. Kondo, J. V. Morey, J. C. Morgan, H. Naka, D. Nobuto, P. R. Raithby, M. Uchiyama, A. E. H. Wheatley, J. Am. Chem. Soc. 2007, 129, 12734-12738.
34. J. Garcia-Álvarez, A. R. Kennedy, J. Klett, R. E. Mulvey, Angew. Chem. 2007, 119, 1123-1126
35. Angew. Chem. Int. Ed. 2007, 46, 1105-1108
36. V. L. Blair, W. Clegg, B. Conway, E. Hevia, A. Kennedy, J. Klett, R. E. Mulvey, L. Russo, Chem. Eur. J. 2008, 14, 65-72
37. V. L. Blair, W. Clegg, R. E. Mulvey, L. Russo, Inorg. Chem. 2009, 48, 8863-8870.
38. H. Naka, M. Uchiyama, Y. Matsumoto, A. E. H. Wheatley, M. McPartlin, J. V. Morey, Y. Kondo, J. Am. Chem. Soc. 2007, 129, 1921-1930
39. B. Conway, E. Hevia, J. García-Álvarez, D. V. Graham, A. R. Kennedy, R. E. Mulvey, Chem. Commun. 2007, 5241-5243
40. H. Naka, J. V. Morey, J. Haywood, D. J. Eisler, M. McPartlin, F. García, H. Kudo, Y. Kondo, M. Uchiyama, A. E. H. Wheatley, J. Am. Chem. Soc. 2008, 130, 16193-16200.
41. R. P. Davies, S. Hornauer, P. B. Hitchcock, Angew. Chem. 2007, 119, 5283-5286
42. Angew. Chem. Int. Ed. 2007, 46, 5191-5194
43. S. Usui, Y. Hashimoto, J. V. Morey, A. E. H. Wheatley, M. Uchiyama, J. Am. Chem. Soc. 2007, 129, 15102-15103
44. J. Haywood, J. V. Morey, A. E. H. Wheatley, C.-Y. Liu, S. Yasuike, J. Kurita, M. Uchiyama, P. R. Raithby, Organometallics 2009, 28, 38-41.
45. for example, W. Clegg, K. Izod, W. McFarlane, P. O'Shaughnessy, Organometallics 1999, 18, 3950-3952.
46. for example, P. J. Bailey, T. Barnett, S. Parsons, J. Organomet. Chem. 2001, 625, 236-244.
47. W. Zarges, M. Marsch, K. Harms, W. Koch, G. Frenking, G. Boche, Chem. Ber. 1991, 124, 543-549.
48. For a detailed analysis of the electronic structure of an α-lithiated benzylsilane see, H. Ott, C. Däschlein, D. Leusser, D. Schildbach, T. Seibel, D. Stalke, C. Strohmann, J. Am. Chem. Soc. 2008, 130, 11901-11911.
49. S. P. Patterman, I. L. Karle, G. D. Stucky, J. Am. Chem. Soc. 1970, 92, 1150-1157
50. J. J. Brooks, G. D. Stucky, J. Am. Chem. Soc. 1972, 94, 7333-7338
51. M. M. Olmstead, P. P. Power, J. Am. Chem. Soc. 1985, 107, 2174-2175
52. M. A. Beno, H. Hope, M. M. Olmstead, P. P. Power, Organometallics 1985, 4, 2117-2121
53. R. A. Bartlett, H. V. R. Dias, P. P. Power, J. Organomet. Chem. 1988, 341, 1-9
54. L. M. Engelhardt, W.-P. Leung, C. L. Raston, G. Salem, P. Twiss, A. H. White, J. Chem. Soc. Dalton Trans. 1988, 2403-2409
55. W. Zarges, M. Marsch, K. Harms, G. Boche, Chem. Ber. 1989, 122, 2303-2309
56. H. Bock, K. Ruppert, Z. Havlas, W. Bensch, W. Hönle, H. G. von Schnering, Angew. Chem. 1991, 103, 1197-1200
57. Angew. Chem. Int. Ed. Engl. 1991, 30, 1183-1186
58. J. Arnold, V. Knapp, J. A. R. Schmidt, A. Shafir, J. Chem. Soc. Dalton Trans. 2002, 3273-3274
59. I. Fernández, E. Martínez-Vivente, F. Breher, P. S. Pregosin, Chem. Eur. J. 2005, 11, 1495-1506.
60. Z.-X. Wang, C.-Y. Qi, Dalton Trans. 2005, 996-1001.
61. P. Beak, S. T. Kerrick, D. J. Gallagher, J. Am. Chem. Soc. 1993, 115, 10628-10636
62. J. Clayden, J. H. Pink, N. Westlund, C. S. Frampton, J. Chem. Soc. Perkin Trans. 1 2002, 901-917.