Benzylic arylation of 2-methyl-5-membered heterocycles using TMP-bases

Organic Letters

Volumn 14, Issue 8, 2012, Pages 1951-1953

  Duez, Stéphanie ^a   Steib, Andreas K ^a   Knochel, Paul ^a  

^a UNIVERSITY OF MUNICH   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

BROMINATED HYDROCARBON; HETEROCYCLIC COMPOUND; PALLADIUM;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; SYNTHESIS;

CATALYSIS; HETEROCYCLIC COMPOUNDS; HYDROCARBONS, BROMINATED; MOLECULAR STRUCTURE; PALLADIUM;

EID: 84860118229     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol300517q     Document Type: Article

References (67)

1. Nicolaou, K. C.; Scarpelli, R.; Bollbuck, B.; Werschkun, B.; Pereira, M. M. A.; Wartmann, M.; Altmann, K.-H.; Zaharevitz, D.; Gussio, R.; Giannakakou, P. Chem. Biol. 2000, 7, 593
2. Oliva, B.; Miller, K.; Caggiano, N.; ÓNeill, A. J.; Cuny, G. D.; Hoemann, M. Z.; Hauske, J. R.; Chopra, I. Antimicrob. Agents Chemother. 2003, 47, 458
3. Bouillon, A.; Voisin, A. S.; Robic, A.; Lancelot, J.-C.; Collot, V.; Rault, S. J. Org. Chem. 2003, 68, 10178
4. Nolan, E. M.; Jaworski, J.; Okamoto, K.-I.; Hayashi, Y.; Sheng, M.; Lippard, S. J. J. Am. Chem. Soc. 2005, 127, 16812
5. Hayashi, A.; Arai, M.; Fujita, M.; Kobayashi, M. Biol. Pharm. Bull. 2009, 32, 1261
6. Quiroga, J.; Trilleras, J.; Insuasty, B.; Abonia, R.; Nogueras, M.; Marchal, A.; Cobo, J. Tetrahedron Lett. 2010, 51, 1107
7. Laird, T. Org. Process Res. Dev. 2006, 10, 851
8. Yurovskaya, M. A.; Karchava, A. V. Chem. Heterocycl. Compd. 1994, 30, 1331
9. Baxter, P. N. W.; Lehn, J.-M.; Fischer, J.; Youinou, M.-T. Angew. Chem. 1994, 106, 2432
10. Angew. Chem., Int. Ed. 1994, 33, 2284.
11. Lehn, J.-M. Science 2002, 295, 2400
12. Chen, X.; Engle, K. M.; Wang, D.-H.; Yu, J. Q. Angew. Chem. 2009, 121, 5196
13. Angew. Chem., Int. Ed. 2009, 48, 5094.
14. Burton, P. M.; Morris, J. A. Org. Lett. 2010, 12, 5359
15. Niwa, T.; Yorimitsu, H.; Oshima, K. Angew. Chem. 2007, 119, 2697
16. Angew. Chem., Int. Ed. 2007, 46, 2643.
17. Campeau, L.-C.; Schipper, D. J.; Fagnou, K. J. Am. Chem. Soc. 2008, 130, 3266
18. Schipper, D. J.; Campeau, L.-C.; Fagnou, K. Tetrahedron 2009, 65, 3155
19. Mousseau, J. J.; Larivée, A.; Charette, A. B. Org. Lett. 2008, 10, 1641
20. Duez, S.; Steib, A. K.; Manolikakes, S. M.; Knochel, P. Angew. Chem. 2011, 123, 7828
21. Angew. Chem., Int. Ed. 2011, 50, 7686.
22. Trost, B. M.; Thaisrivongs, D. A.; Hartwig, J. J. Am. Chem. Soc. 2011, 133, 12439
23. Ackermann, L.; Barfüsser, S.; Kornhaass, C.; Kapdi, A. R. Org. Lett. 2011, 13, 3082
24. Fleming, P.; O'Shea, D. F. J. Am. Chem. Soc. 2011, 133, 1698
25. Lei, A.; Liu, W.; Liu, C.; Chen, M. Dalton Trans. 2010, 39, 10352
26. Ackermann, L. Modern Arylation Methods; Wiley-VCH: Weinheim, 2009.
27. Ackermann, L.; Vincente, R.; Kapdi, A. R. Angew. Chem. 2009, 121, 9976
28. Angew. Chem., Int. Ed. 2009, 48, 9792.
29. Aoyagi, Y.; Inoue, A.; Koizumi, I.; Hashimoto, R.; Miyafuji, A.; Kunoh, J.; Honma, R.; Akita, Y.; Otha, A. Heterocycles 1992, 33, 257
30. Pivsa-Art, S.; Satoh, T.; Kawamura, Y.; Miura, M.; Nomura, M. Bull. Chem. Soc. Jpn. 1998, 71, 467
31. Chiong, H. A.; Daugulis, O. Org. Lett. 2007, 9, 1449
32. Bellina, F.; Cauteruccio, S.; Mannina, L.; Rossi, R.; Viel, S. J. Org. Chem. 2005, 70, 3997
33. Bellina, F.; Cauteruccio, S.; Di Fiore, A.; Rossi, R. Eur. J. Org. Chem. 2008, 5436
34. Bellina, F.; Cauteruccio, S.; Di Fiore, A.; Marchetti, C.; Rossi, R. Tetrahedron 2008, 64, 6060
35. Toure, B. B.; Lane, B. S.; Sames, D. Org. Lett. 2006, 8, 1979
36. Liégaut, B.; Lapointe, D.; Caron, L.; Vlassova, A.; Fagnou, K. J. Org. Chem. 2009, 74, 1826
37. Roger, J.; Doucet, H. Tetrahedron 2009, 65, 9772
38. Laidaoui, N.; Miloudi, A.; El Abed, D.; Doucet, H. Synthesis 2010, 15, 2553
39. Song, G.; Su, Y.; Gong, X.; Han, K.; Li, X. Org. Lett. 2011, 13, 1968
40. Field, L. D.; Messerle, B. A.; Vuong, K. Q.; Turner, P. Dalton Trans. 2009, 18, 3599
41. Oxenford, S. J.; Wright, J. M.; OBrien, P.; Panday, N.; Shipton, M. R. Tetrahedron Lett. 2005, 46, 8315
42. Sagae, T.; Ogawa, S.; Furukawa, N. Bull. Chem. Soc. Jpn. 1991, 64, 3179
43. Setoh, M.; Kouno, M.; Miyanohana, Y.; Kori, M. (Takeda Pharmaceutical Co. Ltd.) US 2010/41891, 2010.
44. Ellingboe, J. W.; Alessi, T. R.; Dolak, T. M.; Nguyen, T. T.; Tomer, J. D.; Guzzo, F.; Bagli, J. F.; McCaleb, M. L. J. Med. Chem. 1992, 35, 1176
45. Alvarez, M.; Bosch, J.; Feliz, M. J. Heterocycl Chem. 1978, 15, 1089
46. Haag, B.; Mosrin, M.; Ila, H.; Malakhov, V.; Knochel, P. Angew. Chem. 2011, 123, 9968
47. Angew. Chem., Int. Ed. 2011, 50, 9794.
48. Krasovskiy, A.; Krasovskaya, V.; Knochel, P. Angew. Chem. 2006, 118, 3024
49. Angew. Chem., Int. Ed. 2006, 45, 2958.
50. Mulvey, R. E.; Mongin, F.; Uchiyama, M.; Kondo, Y. Angew. Chem. 2007, 119, 3876
51. Angew. Chem., Int. Ed. 2007, 46, 3802.
52. Walker, S. D.; Barder, T. E.; Martinelli, J. R.; Buchwald, S. L. Angew. Chem. 2004, 116, 1907
53. Angew. Chem., Int. Ed. 2004, 43, 1871.
54. Barder, T. E.; Walker, S. D.; Martinelli, J. R.; Buchwald, S. L. J. Am. Chem. Soc. 2005, 127, 4685
55. Altman, R. A.; Buchwald, S. L. Nat. Protocols 2007, 2, 3115
56. Martin, R.; Buchwald, S. L. Acc. Chem. Res. 2008, 41, 1461
57. Mulvey, R. E. Acc. Chem. Res. 2009, 42, 743
58. Whisler, M. C.; MacNeil, S.; Snieckus, V.; Beak, P. Angew. Chem. 2004, 116, 2256
59. Angew. Chem., Int. Ed. 2004, 43, 2206.
60. Ogawa, C.; Gu, Y.; Boudou, M.; Kobayashi, S. Acid Catalysis in Modern Organic Synthesis; Wiley-VCH: Weinheim, 2008; Vol. 2, p 589.
61. Kobayashi, S. Lewis Acids in Organic Synthesis; Wiley: Weinheim, 2000; Vol. 2, p 883.
62. Kobayashi, S.; Hachiya, I.; Araki, M.; Ishitani, H. Tetrahedron Lett. 1993, 34, 3755
63. For a review, see: Stephan, D. W.; Erker, G. Angew. Chem. 2010, 122, 50
64. Angew. Chem., Int. Ed. 2010, 49, 46.
65. Jaric, M.; Haag, B. A.; Unsinn, A.; Karaghiosoff, K.; Knochel, P. Angew. Chem. 2010, 122, 5582
66. Angew. Chem., Int. Ed. 2010, 49, 5451.
67. For preparation of 14, see: Macor, J. E.; Ryan, K.; Newman, M. E. J. Org. Chem. 1989, 54, 4785