Efficient preparation of polyfunctional organometallics via directed ortho -metalation

Synthesis

Volumn , Issue 15, 2010, Pages 2670-2678

  Wunderlich, Stefan H ^a   Bresser, Tomke ^a   Dunst, Cora ^a   Monzon, Gabriel ^a   Knochel, Paul ^a  

^a UNIVERSITY OF MUNICH   (Germany)

Author keywords

catalysis; directed metalation; LiCl; metal amides; organometallics

Indexed keywords

ACID CHLORIDES; ALKYL IODIDES; DIRECTED ORTHO-METALATION; ELECTROPHILES; FUNCTIONALIZED; LICL; METAL AMIDES; METALATIONS;

ALDEHYDES; AMIDES; CATALYSIS; CHLORINE COMPOUNDS; HYDROCARBONS;

THERMOMECHANICAL PULPING PROCESS;

ALDEHYDE DERIVATIVE; AMIDE; CHLORIDE; IODINE DERIVATIVE; IRON; LANTHANUM; MANGANESE; ORGANOMETALLIC COMPOUND; REAGENT;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL REACTION; CHEMICAL REACTION KINETICS; CHEMICAL STRUCTURE; ORTHO METATION; PROTON NUCLEAR MAGNETIC RESONANCE; SYNTHESIS; TEMPERATURE;

EID: 77954920227     PISSN: 00397881     EISSN: 1437210X     Source Type: Journal    
DOI: 10.1055/s-0029-1218845     Document Type: Article

References (44)

1. (a) Snieckus V, Chem. Rev. 1990 90 879
2. (b) Whisler M C., MacNeil S, Beak P, Snieckus V, Angew. Chem. Int. Ed. 2004 43 2206
3. (c) Schlosser M, Angew. Chem. Int. Ed. 2005 44 376
4. (d)Turck A, Plé N, Mongin F, Quéguiner G, Tetrahedron 2001 57 4489
5. (e)Mongin F, Quéguiner G, Tetrahedron 2001 57 4059
6. (f) Leroux F, Jeschke P, Schlosser M, Chem. Rev. 2005 105 827
7. (g)Chinchilla R, Nájera C, Yus M, Chem. Rev. 2004 104 2667
8. (a) Naka H, Uchiyama M, Matsumoto Y, Wheatley A E. H., McPartlin M, Morey J V., Kondo Y, J. Am. Chem. Soc. 2007 129 1921
9. (b) Mulvey R E., Mongin F, Uchiyama M, Kondo Y, Angew. Chem. Int. Ed. 2007 46 3802
10. (c) Naka H, Morey J V., Haywood J, Eisler D J., McPartlin M, Garcia F, Kudo H, Kondo Y, Uchiyama M, Wheatley A E. H., J. Am. Chem. Soc. 2008 130 16193
11. (d)Uchiyama M, Kobayashi Y, Furuyama T, Nakamura S, Kajihara Z, Miyoshi T, Sakamoto T, Kondo Y, Morokuma K, J. Am. Chem. Soc. 2008 130 472
12. (e) Usui S, Hashimoto Y, Morey J V., Wheatley A E. H., Uchiyama M, J. Am. Chem. Soc. 2007 129 15102
13. (f) Chevallier F, Mongin F, Chem. Soc. Rev. 2008 37 595
14. (g) Seggio A, Chevallier F, Vaultier M, Mongin F, J. Org. Chem. 2007 72 6602
15. (h)LHelgoualch J.-M, Seggio A, Chevallier F, Yonehara M, Jeanneau E, Uchiyama M, Mongin F, J. Org. Chem. 2008 73 177
16. (i) Clegg W, Dale S H., Hevia E, Hogg L M., Honeyman G W., Mulvey R E., OHara C T., Russo L, Angew. Chem. Int. Ed. 2008 47 731
17. (j) Alborés P, Carrella L, Clegg W, García-Álvarez P, Kennedy A R., Klett J, Mulvey R E., Rentschler E, Russo L, Angew. Chem. Int. Ed. 2009 48 3317
18. (k)Mulvey R E., Acc. Chem. Res. 2009 42 743
19. (l) Carrella L M., Clegg W, Graham D V., Hogg L M., Kennedy A R., Klett J, Mulvey R E., Rentschler E, Russo L, Angew. Chem. Int. Ed. 2007 46 4662
20. (m) Blair V L., Clegg W, Conway B, Hevia E, Kennedy A, Klett J, Mulvey R E., Russo L, Chem. Eur. J. 2008 14 65
21. (n) Blair V L., Carrella L M., Clegg W, Conway B, Harrington R W., Hogg L M., Klett J, Mulvey R E., Rentschler E, Russo L, Angew. Chem. Int. Ed. 2008 47 6208
22. (o)Blair V L., Carrella L M., Clegg W, Klett J, Mulvey R E., Rentschler E, Russo L, Chem. Eur. J. 2009 15 856
23. (a)Krasovskiy A, Krasovskaya V, Knochel P, Angew. Chem. Int. Ed. 2006 45 2958
24. (b)Lin W, Baron O, Knochel P, Org. Lett. 2006 8 5673
25. (c) Boudet N, Lachs J R., Knochel P, Org. Lett. 2007 9 5525
26. (d) Boudet N, Dubbaka S R., Knochel P, Org. Lett. 2008 10 1715
27. (e) Stoll A H., Knochel P, Org. Lett. 2008 10 113
28. (f) Mosrin M, Knochel P, Org. Lett. 2008 10 2497
29. (a)Wunderlich S H., Knochel P, Angew. Chem. Int. Ed. 2007 46 7685
30. (b)Wunderlich S H., Knochel P, Org. Lett. 2008 10 4705
31. (c)Wunderlich S H., Knochel P, Chem. Commun. 2008 6387
32. Wunderlich S H., Kienle M, Knochel P, Angew. Chem. Int. Ed. 2009 48 7256
33. Wunderlich S H., Knochel P, Angew. Chem. Int. Ed. 2009 48 9717
34. Wunderlich S H., Knochel P, Chem. Eur. J. 2010 16 3304
35. Solinas I, Lutz H D., J. Solid State Chem. 1995 117 34
36. (a)Krasovskiy A, Kopp F, Knochel P, Angew. Chem. Int. Ed. 2006 45 497
37. Metzger A, Gavryushin A, Knochel P, Synlett 2009 1433
38. (a)Knochel P, Yeh M C. P., Berk S C., Talbert J, J. Org. Chem. 1988 53 2390
39. Knochel P, Rao S A., J. Am. Chem. Soc. 1990 112 6146
40. (a)Devasagayaraj A, Stüdemann T, Knochel P, Angew. Chem. Int. Ed. 1995 34 2723
41. (b) Giovannini R, Stüdemann T, Dussin G, Knochel P, Angew. Chem. Int. Ed. 1998 37 2387
42. (c) Giovannini R, Stüdemann T, Devasagayaraj A, Dussin G, Knochel P, J. Org. Chem. 1999 64 3544
43. (d) Jensen A E., Knochel P, J. Org. Chem. 2002 67 79
44. (e) Korn T J., Knochel P, Angew. Chem. Int. Ed. 2005 44 2947