Regioselective functionalization of unreactive carbon-hydrogen bonds

Synlett

Volumn , Issue 20, 2006, Pages 3382-3388

  Daugulis, Olafs ^a   Zaitsev, Vladimir G ^a   Shabashov, Dmitry ^a   Pham, Quynh Nhu ^a   Lazareva, Anna ^a  

^a University of Houston   (United States)

Author keywords

Arylations; C H activation; Catalysis; Cross coupling; Palladium

Indexed keywords

ACETATE SILVER; ACETIC ACID DERIVATIVE; AMINE; ANILIDE; BENZOIC ACID DERIVATIVE; BENZYLAMINE DERIVATIVE; CARBON; CARBOXYLIC ACID DERIVATIVE; HYDROGEN; IODIDE; LIGAND; PALLADIUM ACETATE; PYRIDINE DERIVATIVE; UNCLASSIFIED DRUG;

ALKYNYLATION; ARTICLE; ARYLATION; CATALYSIS; CHEMICAL BOND; STEREOCHEMISTRY;

EID: 33846503323     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2006-956468     Document Type: Article

References (56)

1. Volhard, J. Justus Liebigs Ann. Chem. 1892, 267, 172.
2. Kharasch, M. S.; Isbell, H. S. J. Am. Chem. Soc. 1931, 53, 3053.
3. (a) Kleiman, J. P.; Dubeck, M. J. Am. Chem. Soc. 1963, 85, 1544.
4. (b) Cope, A. C.; Siekman, R. W. J. Am. Chem. Soc. 1965, 87, 3272.
5. (a) Gol'dshleger, N. F.; Tyabin, M. B.; Shilov, A. E.; Shteinman, A. A. Russ. J. Phys. Chem. (Transl., of Zh. Fiz. Khim.) 1969, 43, 1222.
6. (b) Janowicz, A. H.; Bergman, R. G. J. Am. Chem. Soc. 1982, 104, 352.
7. (c) Hoyano, J. K.; Graham, W. A. G. J. Am. Chem. Soc. 1982, 104, 3723.
8. Reviews: (a) Shilov, A. E.; Shul'pin, G. B. Chem. Rev. 1997, 97, 2879.
9. (b) Labinger, J. A.; Bercaw, J. E. Nature (London) 2002, 417, 507.
10. (c) Ritleng, V.; Sirlin, C.; Pfeffer, M. Chem. Rev. 2002, 102, 1731.
11. (d) Kakiuchi, F.; Chatani, N. Adv. Synth. Catal. 2003, 345, 1077.
12. (a) Chen, H.; Schlecht, S.; Semple, T. C.; Hartwig, J. F. Science 2000, 287, 1995.
13. (b) Cho, J.-Y.; Tse, M. K.; Holmes, D.; Maleczka, R. E. Jr.; Smith, M. R. III Science 2002, 295, 305.
14. (a) Chen, X.; Goodhue, C. E.; Yu, J.-Q. J. Am. Chem. Soc. 2006, 128, 12634.
15. (b) Barder, T. E.; Walker, S. D.; Martinelli, J. R.; Buchwald, S. L. J. Am. Chem. Soc. 2005, 127, 4685.
16. (c) Dyker, G. Angew. Chem., Int. Ed. Engl. 1994, 33, 103.
17. Hassan, J.; Sevignon, M.; Gozzi, C.; Schulz, E.; Lemaire, M. Chem. Rev. 2002, 102, 1359.
18. (a) Masui, K.; Ikegami, H.; Mori, A. J. Am. Chem. Soc. 2004, 126, 5074.
19. (b) Yokota, T.; Sakaguchi, S.; Ishii, Y. Adv. Synth. Catal. 2002, 344, 849.
20. (c) Fujiwara, Y.; Moritani, I.; Ikegami, K.; Tanaka, R.; Teranishi, S. Bull. Chem. Soc. Jpn. 1970, 43, 863.
21. (d) Li, Z.; Li, C.-J. J. Am. Chem. Soc. 2005, 127, 6968.
22. Dasgupta, R.; Maiti, B. R. Ind. Eng. Chem. Proc. Des. Dev. 1986, 25, 381.
23. (a) Moritani, I.; Fujiwara, Y. Tetrahedron Lett. 1967, 8, 1119.
24. (b) Jia, C.; Kitamura, T.; Fujiwara, Y. Acc. Chem. Res. 2001, 34, 633.
25. (c) Dams, M.; De Vos, D. E.; Celen, S.; Jacobs, P. A. Angew. Chem. Int. Ed. 2003, 42, 3512.
26. (d) Boele, M. D. K.; van Strijdonck, G. P. F.; de Vries, A. H. M.; Kamer, P. C. J.; de Vries, J. G.; van Leeuwen, P. W. N. M. J. Am. Chem. Soc. 2002, 124, 1586.
27. (e) Zhang, H.; Ferreira, E. M.; Stoltz, B. M. Angew. Chem. Int. Ed. 2004, 43, 6144.
28. (f) Murai, S.; Kakiuchi, F.; Sekine, S.; Tanaka, Y.; Kamatani, A.; Sonoda, M.; Chatani, N. Nature (London) 1993, 366, 529.
29. (a) Lewis, J. C.; Wiedemann, S. H.; Bergman, R. G.; Ellman, J. A. Org. Lett. 2004, 6, 35.
30. (b) Okazawa, T.; Satoh, T.; Miura, M.; Nomura, M. J. Am. Chem. Soc. 2002, 124, 5286.
31. (a) Tremont, S. J.; Rahman, H. U. J. Am. Chem. Soc. 1984, 106, 5759.
32. (b) McCallum, J. S.; Gasdaska, J. R.; Liebeskind, L. S.; Tremont, S. J. Tetrahedron Lett. 1989, 30, 4085.
33. (c) Hennessy, E. J.; Buchwald, S. L. J. Am. Chem. Soc. 2003, 125, 12084.
34. (d) Bedford, R. B.; Coles, S. J.; Hursthouse, M. B.; Limmert, M. E. Angew. Chem. Int. Ed. 2003, 42, 112.
35. (e) Kametani, Y.; Satoh, T.; Miura, M.; Nomura, M. Tetrahedron Lett. 2000, 41, 2655.
36. (f) Oi, S.; Fukita, S.; Hirata, N.; Watanuki, N.; Miyano, S.; Inoue, Y. Org. Lett. 2001, 3, 2579.
37. (g) Kalyani, D.; Deprez, N. R.; Desai, L. V.; Sanford, M. S. J. Am. Chem. Soc. 2005, 127, 7330.
38. (h) Park, Y. J.; Jo, E.-A.; Jun, C.-H. Chem. Commun. 2005, 1185.
39. (i) Satoh, T.; Miura, M.; Nomura, M. J. Organomet. Chem. 2002, 653, 161.
40. (a) Campeau, L.-C.; Parisien, M.; Leblanc, M.; Fagnou, K. J. Am. Chem. Soc. 2004, 126, 9186.
41. (b) Huang, Q.; Fazio, A.; Dai, G.; Campo, M. A.; Larock, R. C. J. Am. Chem. Soc. 2004, 126, 7460.
42. (c) Faccini, F.; Motti, E.; Catellani, M. J. Am. Chem. Soc. 2004, 126, 78.
43. Williams, B. S.; Leatherman, M. D.; White, P. S.; Brookhart, M. J. Am. Chem. Soc. 2005, 127, 5132.
44. Zaitsev, V. G.; Daugulis, O. J. Am. Chem. Soc. 2005, 127, 4156.
45. Jones, W. D. Acc. Chem. Res. 2003, 36, 140.
46. Daugulis, O.; Zaitsev, V. G. Angew. Chem. Int. Ed. 2005, 44, 4046.
47. Powell, J.; Horvath, M.; Lough, A. J. Chem. Soc., Chem. Commun. 1993, 733.
48. Canty, A. J.; Patel, J.; Rodemann, T.; Ryan, J. H.; Skelton, B. W.; White, A. H. Organometallics 2004, 23, 3466.
49. Shabashov, D.; Daugulis, O. Org. Lett. 2005, 7, 3657.
50. (a) Myers, A. G.; Tanaka, D.; Mannion, M. R. J. Am. Chem. Soc. 2002, 124, 11250.
51. (b) Fuchita, Y.; Yoshinaga, K.; Ikeda, Y.; Kinoshita-Kawashima, J. J. Chem. Soc., Dalton Trans. 1997, 2495.
52. Dupont, J.; Consorti, C. S.; Spencer, J. Chem. Rev. 2005, 105, 2527.
53. Zhang, Q.; Lu, X.; Han, X. J. Org. Chem. 2001, 66, 7676.
54. Zaitsev, V. G.; Shabashov, D.; Daugulis, O. J. Am. Chem. Soc. 2005, 127, 13154.
55. (a) Giri, R.; Chen, X.; Yu, J.-Q. Angew. Chem. Int. Ed. 2005, 44, 2112.
56. (b) Chen, X.; Li, J.-J.; Hao, X.-S.; Goodhue, C. E.; Yu, J.-Q. J. Am. Chem. Soc. 2006, 128, 78.