Concerning the structures of alkali-metal-mediated ortho zincation of benzamides and phenyl O -carbamate

Organometallics

Volumn 30, Issue 1, 2011, Pages 145-152

  Balloch, Liam ^a   Kennedy, Alan R ^a   Mulvey, Robert E ^a   Rantanen, Toni ^b   Robertson, Stuart D ^a   Snieckus, Victor ^b  

^a UNIVERSITY OF STRATHCLYDE   (United Kingdom)

^b QUEEN S UNIVERSITY   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

AROMATIC FRAGMENTS; BENZAMIDES; C-H BOND; ELECTRON-RICH AROMATICS; METALATIONS; MOLAR EQUIVALENT; NMR ANALYSIS; NMR SPECTROSCOPY; RING STRUCTURES; SALT METATHESIS; TEMPERATURE CONDITIONS; ZINCATION;

AROMATIC COMPOUNDS; AROMATIZATION; INDUSTRIAL CHEMICALS; IODINE; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; THERMOMECHANICAL PULPING PROCESS; X RAY CRYSTALLOGRAPHY;

ZINC;

EID: 78650909109     PISSN: 02767333     EISSN: 15206041     Source Type: Journal    
DOI: 10.1021/om1009654     Document Type: Article

References (51)

1. Hartung, G. C.; Snieckus, V. In Modern Arene Chemistry; Astruc, D., Ed.; Wiley-VCH: New York, 2002; p 330.
2. Macklin, T.; Snieckus, V. In Handbook of C-H Transformations; Dyker, G., Ed.; Wiley-VCH: New York, 2005; pp 106 - 119.
3. Clayden, J. Organolithiums: Selectivity for Synthesis; Pergamon, Elsevier Science: Oxford, 2002; Chapter 2.
4. Snieckus, V. Chem. Rev. 1990, 90, 879
5. For recent mechanistic studies on O -carbamates, see: Riggs, J. C.; Singh, K. J.; Yun, M.; Collum, D. B. J. Am. Chem. Soc. 2008, 130, 2206
6. Whisler, M. C.; MacNeil, S.; Snieckus, V.; Beak, P. Angew. Chem., Int. Ed. 2004, 43, 2206-2225
7. Gilman, H.; Bebb, R. L. J. Am. Chem. Soc. 1938, 61, 109
8. Wittig, G.; Pockels, U.; Dröge, H. Ber. Dtsch. Chem. Ges. 1938, 71, 1903
9. Gschwend, H. W.; Rodriguez, H. R. Org. React. 1979, 26, 1
10. Anctil, E.; Snieckus, V. In Metal-Catalyzed Cross-Coupling Reactions, 2nd Ed.; Diederich, F., de Meijere, A. Eds.; 2004, pp 761 - 813.
11. Knochel, P.; Leuser, H.; Gong, L. Z.; S, Perrone; Kneisel, F. F. In Handbook of Functionalised Organometallics; Knochel, P., Ed.; Wiley-VCH: Weinheim, 2005.
12. Rappoport, Z.; Marek, I. The Chemistry of Organozinc Compounds; Wiley: Chichester, UK, 2006; pp 322 - 378.
13. Wunderlich, S. H.; Knochel, P. Angew. Chem., Int. Ed. 2007, 46, 7985
14. Dong, Z.; Closoki, G. C.; Wunderlich, S. H.; Unsinn, A.; Li, J.; Knochel, P. Chem.-Eur. J. 2009, 15, 457
15. Rohbogner, C. J.; Wunderlich, S. H.; Clososki, G. C.; Knochel, P. Eur. J. Org. Chem. 2009, 1781
16. Kondo, Y.; Shilai, M.; Uchiyama, M.; Sakamoto, T. J. Am. Chem. Soc. 1999, 121, 3539
17. Uchiyama, M.; Matsumoto, Y.; Nobuto, D.; Furuyama, T.; Yamaguchi, K.; Morokuma, K. J. Am. Chem. Soc. 2006, 128, 8748
18. Andrikopoulos, P. C.; Armstrong, D. R.; Barley, H. R. L.; Clegg, W.; Dale, S. H.; Hevia, E.; Honeyman, G. W.; Kennedy, A. R.; Mulvey, R. E. J. Am. Chem. Soc. 2005, 127, 6184
19. Armstrong, D. R.; García-Álvarez, J.; Graham, D. V.; Honeyman, G. W.; Hevia, E.; Kennedy, A. R.; Mulvey, R. E. Chem.-Eur. J. 2009, 15, 3800
20. Armstrong, D. R.; Clegg, W.; Dale, S. H.; Hevia, E.; Hogg, L. M.; Honeyman, G. W.; Mulvey, R. E. Angew. Chem., Int. Ed. 2006, 45, 3775
21. Balloch, L.; Kennedy, A. R.; Klett, J.; Mulvey, R. E.; OHara, C. T. Chem. Commun. 2010, 46, 2319
22. Armstrong, D. R.; Clegg, W.; Dale, S. H.; Graham, D. V.; Hevia, E.; Hogg, L. M.; Honeyman, G. W.; Kennedy, A. R.; Mulvey, R. E. Chem. Commun. 2007, 598
23. Clegg, W.; Dale, S. H.; Hevia, E.; Hogg, L. M.; Honeyman, G. W.; Mulvey, R. E.; OHara, C. T. Angew. Chem., Int. Ed. 2006, 45, 6548
24. Clayden, J.; Davies, R. P.; Hendy, M. A.; Snaith, R.; Wheatley, A. E. H. Angew. Chem., Int. Ed. 2001, 40, 1238
25. Clegg, W.; Dale, S. H.; Hevia, E.; Honeyman, G. W.; Mulvey, R. E. Angew. Chem., Int. Ed. 2006, 45, 2370
26. Clegg, W.; Dale, S. H.; Harrington, R. W.; Hevia, E.; Honeyman, G.; Mulvey, R. E. Angew. Chem., Int. Ed. 2006, 45, 2374
27. García-Álvarez, J.; Graham, D. V.; Kennedy, A. R.; Mulvey, R. E.; Weatherstone, S. Chem. Commun. 2006, 3208
28. Conway, B.; Hevia, E.; García-Álvarez, J.; Graham, D. V.; Kennedy, A. R.; Mulvey, R. E. Chem. Commun. 2007, 5241
29. Kondo, Y.; Morey, J. V.; Morgan, J. C.; Naka, H.; Nobuto, D.; Raithby, P.; Uchiyama, M.; Wheatley, A. E. H. J. Am. Chem. Soc. 2007, 129, 12734
30. Blair, V. L.; Clegg, W.; Conway, B.; Hevia, E.; Kennedy, A. R.; Klett, J.; Mulvey, R. E.; Russo, L. Chem.-Eur. J. 2008, 14, 65
31. Naka, H.; Morey, J. V.; Haywood, J.; Eisler, D. J.; McPartlin, M.; García, F.; Kudo, H.; Kondo, Y.; Uchiyama, M.; Wheatley, A. E. H. J. Am. Chem. Soc. 2008, 130, 16193
32. For an example of an in situ Li-Cd base see: Snégaroff, K.; LHelgoualch, J.-M.; Bentabed-Ababsa, G.; Nguyen, T. T.; Chevallier, F.; Yonehara, M.; Uchiyama, M.; Derdour, A.; Mongin., F. Chem.-Eur. J. 2009, 15, 10280
33. Beak, P.; Snieckus, V. Acc. Chem. Res. 1982, 15, 306
34. Puterbaugh, W. H.; Hauser, C. R. J. Org. Chem. 1964, 29, 853
35. Beak, P.; Brubaker, G. R.; Farney, R. F. J. Am. Chem. Soc. 1976, 98, 3621
36. Beak, P.; Brown, R. A. J. Org. Chem. 1977, 42, 1823
37. Schumann, U.; Behrens, U.; Weiss, E. Angew. Chem., Int. Ed. 1989, 28, 476
38. Izod, K.; Stewart, J. C.; Clegg, W.; Harrington, R. W. Dalton Trans. 2007, 257
39. Steigelmann, M.; Nisar, Y.; Rominger, F.; Goldfuss, B. Chem.-Eur. J. 2002, 8, 5211
40. Gardiner, M. G.; Lawrence, S. M.; Raston, C. L.; Skelton, B. W.; White, A. H. Chem. Commun. 1996, 2491
41. Bukhaltsev, E.; Goldberg, I.; Vigalok, A. Organometallics 2005, 24, 5732
42. Sibi, M. P.; Snieckus, V. J. Org. Chem. 1983, 48, 1937
43. García, F.; McPartlin, M.; Morey, J. V.; Nobuto, D.; Kondo, Y.; Naka, H.; Uchiyama, M.; Wheatley, A. E. H. Eur. J. Org. Chem. 2008, 644
44. Nobuto, D.; Uchiyama, M. J. Org. Chem. 2008, 73, 1117
45. Clegg, W.; Conway, B.; Hevia, E.; McCall, M. D.; Russo, L.; Mulvey, R. E. J. Am. Chem. Soc. 2009, 131, 2375
46. Armstrong, D. R.; Blair, V. L.; Clegg, W.; Dale, S. H.; García-Álvarez, J.; Honeyman, G. W.; Hevia, E.; Mulvey, R. E.; Russo, L. J. Am. Chem. Soc. 2010, 132, 9480
47. CSD version 5.31 see: Allen, F. H. Acta Crystallogr., Sect. B 2002, 58, 380
48. 3) solvate via oxidative addition; see: Bocelli, G.; Catellani, M.; Chiusoli, G. P.; Cugini, F.; Lasagni, B.; Mari, M. N. Inorg. Chim. Acta 1998, 270, 123
49. 6 solution during this work.
50. Schade, C.; Bauer, W.; Schleyer, P. v. R. J. Organomet. Chem. 1985, 295, c25
51. Sheldrick, G. M. Acta Crystallogr., Sect. A: Found. Crystallogr. 2008, 64, 112