Mild Ullmann-type biaryl ether formation reaction by combination of ortho-substituent and ligand effects

Angewandte Chemie - International Edition

Volumn 45, Issue 8, 2006, Pages 1276-1279

  Cai, Qian ^a   Zou, Benli ^b   Ma, Dawei ^a  

^a SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

^b FUDAN UNIVERSITY   (China)

Author keywords

Biaryl ethers; Coupling; Ligand effects; ortho effect; Peptides

Indexed keywords

BIARYL ETHERS; COUPLING; LIGAND EFFECTS; ORTHO EFFECT; PEPTIDES;

HALOGEN COMPOUNDS; ISOMERS; MOLECULAR STRUCTURE; ORGANIC SOLVENTS; REACTION KINETICS; SUBSTITUTION REACTIONS;

ETHERS;

COPPER; ETHER DERIVATIVE; LIGAND;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; SYNTHESIS; TEMPERATURE;

COPPER; ETHERS; LIGANDS; MOLECULAR STRUCTURE; TEMPERATURE;

EID: 33745694711     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200503538     Document Type: Article

References (54)

1. For reviews, see: a) K. C. Nicolaou, C. N. C. Boddy, S. Bräse, N. Winssinger, Angew. Chem. 1999, 111, 2230-2287;
2. Angew. Chem. Int. Ed. 1999, 38, 2096-2152;
3. b) J. Zhu, Synlett 1997, 133-144;
4. c) A. V. R. Rao, M. K. Gurjar, G. K. L. Reddy, A. S. Rao, Chem. Rev. 1995, 95, 2135-2167;
5. d) J. Blankenstein, J. Zhu, Eur. J. Org. Chem. 2005, 1949-1964.
6. a) K. C. Nicolaou, C. N. C. Boddy, S. Natarajan, T.-Y. Yue, H. Li, S. Bräse, J. M. Ramanjulu, J. Am. Chem. Soc. 1997, 119, 3421-3422;
7. b) K. C. Nicolaou, S. Natarajan, H. Li, N. F. Jain, R. Hughes, M. E. Solomon, J. M. Ramanjulu, C. N. C. Boddy, M. Takayanagi, Angew. Chem. 1998, 110, 2872-2878;
8. Angew. Chem. Int. Ed. 1998, 37, 2708-2714;
9. c) K. C. Nicolaou, N. F. Jain, S. Natarajan, R. Hughes, M. E. Solomon, H. Li, J. M. Ramanjulu, M. Takayanagi, A. E. Koumbis, T. Bando, Angew. Chem. 1998, 110, 2879-2881;
10. Angew. Chem. Int. Ed. 1998, 37, 2714-2716;
11. d) K. C. Nicolaou, M. Takayanagi, N. F. Jain, S. Natarajan, A. E. Koumbis, T. Bando, J. M. Ramanjulu, Angew. Chem. 1998, 110, 2881-2883;
12. Angew. Chem. Int. Ed. 1998, 37, 2717-2719;
13. e) D. A. Evans, M. R. Wood, B. W. Trotter, T. I. Richardson, J. C. Barrow, J. L. Katz, Angew. Chem. 1998, 110, 2864-2868;
14. Angew. Chem. Int. Ed. 1998, 37, 2700-2704;
15. f) D. A. Evans, C. J. Dinsmore, P. S. Watson, M. R. Wood, T. I. Richardson, B. W. Trotter, J. L. Katz, Angew. Chem. 1998, 110, 2868-2872;
16. Angew. Chem. Int. Ed. 1998, 37, 2704-2708;
17. g) D. L. Boger, S. Miyazaki, S. H. Kim, J. H. Wu, O. Loiseleur, S. L. Castle, J. Am. Chem. Soc. 1999, 121, 3226-3227.
18. B. M. Crowley, Y. Mori, C. C. McComas, D. Tang, D. L. Boger, J. Am. Chem. Soc. 2004, 126, 4310-4317.
19. a) D. A. Evans, J. L. Katz, G. S. Peterson, T. Hintermann, J. Am. Chem. Soc. 2001, 123, 12411-12413;
20. b) D. L. Boger, S. H. Kim, S. Miyazaki, H. Strittmatter, J.-H. Wang, Y. Mori, O. Rogel, S. L. Castle, J. J. McAtee, J. Am. Chem. Soc. 2000, 122, 7416-7417;
21. c) D. L. Boger, S. H. Kim, Y. Mori, J.-H. Wang, O. Rogel, S. L. Castle, J. J. McAtee, J. Am. Chem. Soc. 2001, 123, 1862-1871.
22. For selected references, see: a) J. W. Janetka, D. H. Rich, J. Am. Chem. Soc. 1997, 119, 6488-6495;
23. b) S. Nishiyama, Y. Suzuki, S. Yamamura, Tetrahedron Lett. 1989, 30, 379-382;
24. c) A. V. R. Rao, T. K. Chakraborty, K. L. Reddy, A. S. Rao, Tetrahedron Lett. 1992, 33, 4799-4802;
25. d) A. Bigot, M. Bois-Choussy, J. Zhu, Tetrahedron Lett. 2000, 41, 4573-4577.
26. a) D. L. Boger, D. Yohannes, J. Am. Chem. Soc. 1991, 113, 1427-1429;
27. b) D. L. Boger, D. Yohannes, J. Zhou, M. A. Patane, J. Am. Chem. Soc. 1993, 115, 3420-3430;
28. c) D. L. Boger, J. Zhou, J. Am. Chem. Soc. 1995, 117, 7364-7378;
29. for their initial efforts on related studies, see: d) D. L. Boger, D. Yohannes, Tetrahedron Lett. 1989, 30, 2053-2056;
30. e) D. L. Boger, D. Yohannes, J. Org. Chem. 1990, 55, 6000-6017;
31. f) D. L. Boger, D. Yohannes, J Org. chem. 1991, 56, 1763-1767;
32. g) D. L. Boger, Y. Nomoto, B. R. Teegarden, J. Org. Chem. 1993, 58, 1425-1433.
33. a) M. Bois-Choussy, P. Cristau, J. Zhu, Angew. Chem. 2003, 115, 4370-4373;
34. Angew. Chem. Int. Ed. 2003, 42, 4238-4241;
35. b) P. J. Krenitsky, D. L. Boger, Tetrahedron Lett. 2002, 43, 407-410.
36. H. Deng, J.-K. Jung, T. Liu, K. W. Kuntz, M. L. Snapper, A. H. Hoveyda, J. Am. Chem. Soc. 2003, 125, 9032-9034.
37. M. E. Jung, T. I. Lazarova, J. Org. Chem. 1999, 64, 2976-2977.
38. For reviews, see: a) S. V. Ley, A. W. Thomas, Angew. Chem. 2003, 115, 5558-5607;
39. Angew. Chem. Int. Ed. 2003, 42, 5400-5449;
40. b) K. Kunz, U. Scholz, D. Ganzer, Synlett 2003, 15, 2428-2439;
41. c) I. P. Beletskaya, A. V. Cheprakov, Coord. Chem. Rev. 2004, 248, 2337-2364.
42. a) D. Ma, Q. Cai, Org. Lett. 2003, 5, 3799-3802;
43. b) J.-F. Marcoux, S. Doye, S. L. Buchwald, J. Am. Chem. Soc. 1997, 119, 10539-10540;
44. c) E. Buck, Z. J. Song, D. Tschaen, P. G. Dormer, R. P. Volante, P. J. Reider, Org. Lett. 2002, 4, 1623-1626;
45. d) H.-J. Cristau, R. P. Cellier, S. Hamada, J.-F. Spindler, M. Taillefer, Org. Lett. 2004, 6, 913-916.
46. a) J. Lindley, Tetrahedron 1984, 40, 1433-1456;
47. b) R. Cirigottis, E. Ritchie, W. C. Taylor, Aust. J. Chem. 1974, 27, 2209-2228;
48. c) A. Bruggink, A. Mckillop, Tetrahedron 1975, 31, 2607-2619;
49. d) A. V. Kalinin, J. F. Bower, P. Riebel, V. Snieckus, J. Org. Chem. 1999, 64, 2986-2987.
50. a) S. J. Tremont, H. U Rahman, J. Am. Chem. Soc. 1984, 106, 5759-5760;
51. for recent studies using these these complexes as intermediates, see : b) O. Daugulis, V. G. Zaitsev, Angew. Chem. 2005, 117, 4114-4416;
52. Angew. Chem. Int. Ed. 2005, 44, 4046-4048;
53. c) V. G. Zaitsev, O. Daugulis, J. Am. Chem. Soc. 2005, 127, 4156-4157;
54. d) M. D. K. Boele, G. P. F. Strijdonck, A. H. M. Vries, P. C. J. Kamer, J. G. Vries, P. W. N. M. Leeuwen, J. Am. Chem. Soc. 2002, 124, 1586-1587.