Lithium cadmate-mediated deprotonative metalation of anisole: Experimental and computational study

Journal of Organic Chemistry

Volumn 75, Issue 9, 2010, Pages 3117-3120

  Snégaroff, Katia ^a   Komagawa, Shinsuke ^b   Yonehara, Mitsuhiro ^b   Chevallier, Floris ^a   Gros, Philippe C ^c   Uchiyama, Masanobu ^b   Mongin, Florence ^a  

^a Chimie et Photonique Moleculaires Rennes   (France)

^b INST OF PHYS AND CHEMICAL RESEARCH   (Japan)

^c NANCY UNIVERSITÉ   (France)

Author keywords

[No Author keywords available]

Indexed keywords

COMPUTATIONAL STUDIES; DFT CALCULATION; METALATIONS; REACTION PATHWAYS;

LITHIUM; SULFUR COMPOUNDS;

THERMOMECHANICAL PULPING PROCESS;

AMIDE; ANISOLE; CADMIUM DERIVATIVE; LITHIUM CADMATE; LITHIUM DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; DENSITY FUNCTIONAL THEORY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PROTON TRANSPORT;

EID: 77951772282     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo100150s     Document Type: Article

References (39)

1. For excellent reviews, see: Gschwend, H. W.; Rodriguez, H. R. Org. React. 1979, 26, 1-360
2. Beak, P.; Snieckus, V. Acc. Chem. Res. 1982, 15, 306-312
3. Snieckus, V. Chem. Rev. 1990, 90, 879-933
4. Gant, T. G.; Meyers, A. I. Tetrahedron 1994, 50, 2297-2360
5. Schlosser, M. In Organometallics in Synthesis, 2 nd ed.; Schlosser, M., Ed.; Wiley: New York, 2002; Chapter I.
6. Schlosser, M. Pure Appl. Chem. 1988, 60, 1627-1634
7. Lochmann, L. Eur. J. Inorg. Chem. 2000, 7, 1115-1126
8. Gros, P. C.; Fort, Y. Eur. J. Org. Chem. 2009, 4199-4209
9. For reviews, see: Mulvey, R. E. Organometallics 2006, 25, 1060-1075
10. Mulvey, R. E.; Mongin, F.; Uchiyama, M.; Kondo, Y. Angew. Chem., Int. Ed. 2007, 46, 3802-3824
11. Mulvey, R. E. Acc. Chem. Res. 2009, 42, 743-755
12. Kondo, Y.; Shilai, M.; Uchiyama, M.; Sakamoto, T. J. Am. Chem. Soc. 1999, 121, 3539-3540
13. Uchiyama, M.; Miyoshi, T.; Kajihara, Y.; Sakamoto, T.; Otani, Y.; Ohwada, T.; Kondo, Y. J. Am. Chem. Soc. 2002, 124, 8514-8515
14. Barley, H. R. L.; Clegg, W.; Dale, S. H.; Hevia, E.; Honeyman, G. W.; Kennedy, A. R.; Mulvey, R. E. Angew. Chem., Int. Ed. 2005, 44, 6018-6021
15. Clegg, W.; Dale, S. H.; Hevia, E.; Honeyman, G. W.; Mulvey, R. E. Angew. Chem., Int. Ed. 2006, 45, 2370-2374
16. Clegg, W.; Dale, S. H.; Harrington, R. W.; Hevia, E.; Honeyman, G. W.; Mulvey, R. E. Angew. Chem., Int. Ed. 2006, 45, 2374-2377
17. Clegg, W.; Dale, S. H.; Drummond, A. M.; Hevia, E.; Honeyman, G. W.; Mulvey, R. E. J. Am. Chem. Soc. 2006, 128, 7434-7435
18. Uchiyama, M.; Matsumoto, Y.; Nobuto, D.; Furuyama, T.; Yamaguchi, K.; Morokuma, K. J. Am. Chem. Soc. 2006, 128, 8748-8750
19. Uchiyama, M.; Kobayashi, Y.; Furuyama, T.; Nakamura, S.; Kajihara, Y.; Miyoshi, T.; Sakamoto, T.; Kondo, Y.; Morokuma, K. J. Am. Chem. Soc. 2008, 130, 472-480
20. Clegg, W.; Conway, B.; Hevia, E.; McCall, M. D.; Russo, L.; Mulvey, R. E. J. Am. Chem. Soc. 2009, 131, 2375-2384
21. Wunderlich, S. H.; Knochel, P. Angew. Chem., Int. Ed. 2007, 46, 7685-7688
22. Wunderlich, S.; Knochel, P. Chem. Commun. 2008, 6387-6389
23. Wunderlich, S. H.; Knochel, P. Org. Lett. 2008, 10, 4705-4707
24. Mosrin, M.; Knochel, P. Chem.-Eur. J. 2009, 15, 1468-1477
25. Mosrin, M.; Knochel, P. Org. Lett. 2009, 11, 1837-1840
26. L'Helgoualch, J.-M.; Bentabed-Ababsa, G.; Chevallier, F.; Yonehara, M.; Uchiyama, M.; Derdour, A.; Mongin, F. Chem. Commun. 2008, 5375-5377
27. 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, 10280-10290
28. 2Cd; see ref 9.
29. 3CdLi was not equaled using 0.5 equiv of any of the other Li-Cd combinations. Similar results were obtained in some cases provided that 1 equiv of base was used.
30. LHelgoualch, J.-M.; Bentabed-Ababsa, G.; Chevallier, F.; Derdour, A.; Mongin, F. Synthesis 2008, 4033-4035
31. Dayaker, G.; Sreeshailam, A.; Chevallier, F.; Roisnel, T.; Radha Krishna, P.; Mongin, F. Chem. Commun. 2010, 46, 2862 - 2864.
32. Shannon, M. Heavy Metal Poisoning. In Clinical Management of Poisoning and Drug Overdose, 3 rd ed.; Haddad, L. M.; Shannon, M.; Winchester, J. F., Eds.; Saunders: New York, 1998.
33. Kedarnath, G.; Kumbhare, L. B.; Jain, V. K.; Phadnis, P. P.; Nethaji, M. Dalton Trans. 2006, 2714-2718
34. Frisch, M. J., et al. Gaussian 03, Revision E.01; Gaussian, Inc.: Wallingford, CT, 2004.
35. Becke, A. D. Phys. Rev. 1988, A38, 3098-3100
36. Becke, A. D. J. Chem. Phys. 1993, 98, 1372-1377
37. Becke, A. D. J. Chem. Phys. 1993, 98, 5648-5652
38. Lee, C.; Yang, W.; Parr, R. G. Phys. Rev. 1988, B37, 785-788
39. Schäfer, A.; Horn, H.; Ahlrichs, R. J. Chem. Phys. 1992, 97, 2571-2577