A simple catalytic method for the regioselective halogenation of arenes

Organic Letters

Volumn 8, Issue 12, 2006, Pages 2523-2526

  Kalyani, Dipannita ^a   Dick, Allison R ^a   Anani, Waseem Q ^a   Sanford, Melanie S ^a  

^a UNIVERSITY OF MICHIGAN   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

HALOGENATED HYDROCARBON; PALLADIUM; POLYCYCLIC AROMATIC HYDROCARBON;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; STEREOISOMERISM; SYNTHESIS;

CATALYSIS; HYDROCARBONS, HALOGENATED; MOLECULAR STRUCTURE; PALLADIUM; POLYCYCLIC HYDROCARBONS, AROMATIC; STEREOISOMERISM;

EID: 33745577893     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol060747f     Document Type: Article

References (65)

1. Sotomayor, N.; Lete, E. Curr. Org. Chem. 2003, 7, 275.
2. Handbook of Grignard Reagents; Silverman, G. S., Rakita, P. E., Eds.; Dekker: New York, 1996.
3. Levin, R. H. React. Intermed. (Wiley) 1985, 3, 1.
4. Crampton, M. R. Organic Reaction Mechanisms; Wiley: New York, 2003; p 275.
5. (a) Metal Catalyzed Cross Coupling Reactions; Dieterich, F., Stang, P. J., Eds.; Wiley-VCH: New York, 1998.
6. (b) Prim, D.; Campagne, J. M.; Joseph, D.; Andrioletti, B. Tetrahedron 2002, 58, 2041.
7. (c) Beletskaya, I. P.; Cheprakov, A. V. Coord. Chem. Rev. 2004, 248, 2337.
8. (d) Ley, S. V.; Thomas, A. W. Angew. Chem., Int. Ed. 2003, 42, 5400.
9. (e) Kunz, K.; Scholz, U.; Ganzer, D. Synlett 2003, 2428.
10. (a) Hassan, J.; Sévignon, M.; Gozzi, C., Schulz, E.; Lemaire, M. Chem. Rev. 2002, 102, 1359.
11. (b) Bringmann, G.; Walter, R.; Weirich, R. Angew. Chem., Int. Ed. 1990, 102, 1006.
12. (c) Hartwig, J. F. In Handbook of Organopalladium Chemistry for Organic Synthesis; Wiley-Interscience: New York, 2002, p 1051.
13. (d) Yang, B. H.; Buchwald, S. L. J. Organomet. Chem. 1999, 576, 125.
14. (e) Hartwig, J. F. In Handbook of Organopalladium Chemistry for Organic Synthesis; Wiley-Interscience: New York, 2002, p 1097.
15. Butler, A.; Walker, J. V. Chem. Rev. 1993, 93, 1937.
16. (a) Taylor, R. Electrophilic Aromatic Substitution; John Wiley: New York, 1990.
17. (b) De la Mare, P. B. Electrophilic Halogenation; Cambridge University Press: Cambridge, 1976, Chapter 5.
18. (c) Merkushev, E. B. Synthesis 1988, 923.
19. (a) Zhang, Y.; Shibatomi, K.; Yamamoto, H. Synlett 2005, 18, 2837 and references therein.
20. (b) Prakash, G. K. S.; Mathew, T.; Hoole, D.; Esteves, P. M.; Wang, Q.; Rasul, G.; Olah, G. A. J. Am. Chem. Soc. 2004, 126, 15770.
21. (c) Tanemura, K.; Suzuki, T.; Nishida, Y.; Satsumabayashi, K.; Horaguchi, T. Chem. Lett. 2003, 32, 932.
22. (d) Firouzabadi, H.; Iranpoor, N.; Shiri, M. Tetrahedron Lett. 2003, 44, 8781.
23. (e) Vyas, P. V.; Bhatt, A. K.; Ramachandraiah, G.; Bedekar, A. V. Tetrahedron Lett. 2003, 44, 4085.
24. (f) Lee, K.; Cho, H. K.; Song, C. Bull Korean Chem. Soc. 2002, 23, 773.
25. (g) Iskra, J.; Stavber, S.; Zupan, M. Synthesis 2004, 11, 1869.
26. (h) Dewkar, G. K.; Narina, S. V.; Sudalai, A. Org. Lett. 2003, 5, 4501.
27. (i) Tamhankar, B. V.; Desai, U. V.; Mane, R. B.; Wadgaonkar, P. P.; Bedekar, A. V. Synthetic Commun. 2001, 31, 2021.
28. (j) Roche, D.; Prasad, K.; Repic, O.; Blacklock, T. J. Tetrahedron Lett. 2000, 41, 2083.
29. (k) Braddock, D. C.; Cansell, G.; Hermitage, S. A. Synlett 2004, 3, 461.
30. (l) Evans, P. A.; Brandt, T. A. J. Org. Chem. 1997, 62, 5321.
31. Snieckus, V. Chem. Rev. 1990, 90, 879.
32. For some recent examples, see: (a) Young, D. W.; Comins, D. L. Org. Lett. 2005, 7, 5661.
33. (b) McCulloch, M. W. B.; Barrow, R. A. Tetrahedron Lett. 2005, 46, 7619.
34. (c) Pradhan, T. K.; De, A.; Mortier, J. Tetrahedron 2005, 61, 9007.
35. -2 (for Ar-Cl). See: Roy, A. H.; Hartwig, J. F. Organometallics 2004, 23, 1533 and references therein.
36. (a) van Belzen, R.; Elsevier: C. J.; Dedieu, A.; Veldman, N.; Spek, A. L. Organometallics 2003, 22, 722.
37. (b) Alsters, P. L.; Engel, P. F.; Hogerheide, M. P.; Marinus, P. H.; Copijn, M.; Spek, A. L.; van Koten, G. Organometallics 1993, 12, 1831.
38. (c) Kubota, M.; Boegeman, S. C.; Keil, R. N.; Webb, C. G. Organometallics 1989, 8, 1616.
39. (d) Wong, P. K.; Stille, J. K. J. Organomet. Chem. 1974, 70, 121.
40. (e) Bäckvall, J. Acc. Chem. Res. 1983, 16, 335.
41. (f) Bäckvall, J. Tetrahedron Lett. 1977, 18, 467.
42. (g) Alsters, P. L.; Boersma, J.; van Koten, G. Organometallics 1993, 12, 1629.
43. (h) Lagunas, M.-C.; Gossage, R. A.; Spek, A. L.; van Koten, G. Organometallics 1998, 17, 731.
44. (a) Desai, L. V.; Malik, H. A.; Sanford, M. S. Org. Lett. 2006, 8, 1141.
45. (b) Kalyani, D.; Sanford, M. S. Org. Lett. 2005, 7, 4149.
46. (c) Desai, L. V.; Hull, K. L.; Sanford, M. S. J. Am. Chem. Soc. 2004, 126, 9542.
47. (d) Dick, A. R.; Hull, K. L. Sanford, M. S. J. Am Chem. Soc. 2004, 126, 2300.
48. (e) Kalyani, D.; Deprez, N. R.; Desai, L. V.; Sanford, M. S. J. Am. Chem. Soc. 2005, 127, 7330.
49. (a) Giri, R.; Chen, X.; Yu, J.-Q. Angew. Chem., Int. Ed. 2005, 44, 2112.
50. (b) Lei, A.; Lu, X.; Liu, G. Tetrahedron Lett. 2004, 45, 1785.
51. (c) Manzoni, M. R.; Zabawa, T. P.; Kasi, D.; Chemler, S. R. Organometallics 2004, 23, 5618.
52. (d) El-Qisairi, A. K.; Qaseer, H. A.; Katsigras, G.; Lorenzi, P.; Trivedi, U.; Tracz, S.; Hartman, A.; Miller, J. A.; Henry, P. M. Org. Lett. 2003, 5, 439 and references therein.
53. (e) Zhu, G.; Lu, X. J. Organomet. Chem. 1996, 508, 83 and references therein.
54. (f) Henry, P. M. J. Org. Chem. 1971, 36, 1886.
55. (g) Fahey, D. R. J. Organomet. Chem. 1971, 27, 283.
56. An initial screen of the reaction of 2-phenylpyridine with NCS in 11 different solvents revealed that the highest yields were obtained in MeCN and AcOH. As a result, further investigations focused on these two solvents.
57. 2 in AcOH afforded traces (5% by GC) of a monochlorinated product.
58. Daugulis, O.; Zaitsev, V. G. Angew. Chem., Int. Ed. 2005, 44, 4046.
59. Togo, H.; Sakuratani, K. Synlett 2002, 1966.
60. Notably, bromination of 1 with NBS (and bromination reactions in general) proceeded in lower yield than the analogous chlorinations or iodinations. The yield was independent of the source or quality (recrystallized versus nonrecrystallized) of the NBS. The predominant side products appeared to be traces of the corresponding dibrominated product along with mixtures of oxidatively coupled arylpyridines (dimers of 1, heterodimers of 1 with 1-Br, etc.). Interestingly, no acetoxylated side products were observed with NBS, even in AcOH.
61. 2. See ref 15a.
62. 2 in the reaction of 1 with NXS resulted in somewhat lower yields of 1-Cl, 1-Br, and 1-I (60%, 41%, and 77% GC yield, respectively).
63. (a) Oi, S.; Fukita, S.; Hirata, N.; Watanuki, N.; Miyano, S.; Inoue, Y. Org. Lett. 2001, 3, 2579 and references therein;
64. (b) Chatani, N.; Ie, Y.; Kakiuchi, F.; Murai, S. J. Org. Chem. 1998, 62, 2604.
65. GC analysis of the isolated product showed ∼10% of a regioisomeric product both with and without Pd.