Highly efficient cross-dehydrogenative-coupling between ethers and active methylene compounds

Angewandte Chemie - International Edition

Volumn 45, Issue 12, 2006, Pages 1949-1952

  Zhang, Yuhua ^a   Li, Chao Jun ^b  

^a Tulane University   (United States)

^b MCGILL UNIVERSITY   (Canada)

Author keywords

C C coupling; C H activation; Copper; Homogeneous catalysis; Indium

Indexed keywords

CATALYSTS; CHEMICAL BONDS; COPPER; DEHYDROGENATION; INDIUM; OLEFINS; REACTION KINETICS;

ACTIVE METHYLENE COMPOUND; C-C COUPLING; C-H ACTIVATION; HOMOGENEOUS CATALYSIS;

ETHERS;

EID: 33645464350     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200503255     Document Type: Article

References (66)

1. For reviews, see: a) V. Ritleng, C. Sirlin, M. Pfeffer, Chem. Rev. 2002, 102, 1731-1769;
2. b) G. Dyker, Angew. Chem. 1999, 111, 1808-1822;
3. Angew. Chem. Int. Ed. 1999, 38, 1698-1712;
4. c) T. Naota, H. Takaya, S. I. Murahashi, Chem. Rev. 1998, 98, 2599-2660;
5. for some recent examples, see: d) N. Chatani, T. Asaumi, S. Yorimitsu, T. Ikeda, F. Kakiuchi, S. Murai, J. Am. Chem. Soc. 2001, 123, 10 935-10 941;
6. e) L. J. Gooßen, Angew. Chem. 2001, 113, 3929-3932;
7. Angew. Chem. Int. Ed. 2002, 41, 3775-3778;
8. f) B. A. Arndtsen, R. G. Bergman, T. A. Mobley, T. H. Peterson, Acc. Chem. Res. 1995, 28, 154-162;
9. g) H. Chen, S. Schlecht, T. C. Semple, J. F. Hartwig, Science 2000, 287, 1995;
10. h) A. S. Goldman, Nature 1993, 366, 514;
11. i) R. H. Crabtree, J. Organomet. Chem. 2004, 689, 4083-4091;
12. j) C. Jia, T. Kitamura, Y. Fujiwara, Acc. Chem. Res. 2001, 34, 633-639.
13. a) C.-J. Li, Acc. Chem. Res. 2002, 35, 533-538;
14. b) C.-J. Li, Chem. Rev. 2005, 105, 3095-3166;
15. c) C. Wei, Z. Li, C.-J. Li, Synlett 2004, 1472-1483;
16. d) C.-J. Li, Chem. Rev. 1993, 93, 2023-2035.
17. a) Z. Li, C.-J. Li, J. Am. Chem. Soc. 2005, 127, 6968-6969;
18. b) Z. Li, C.-J. Li, J. Am. Chem. Soc. 2005, 127, 3672-3673;
19. c) Z. Li, C.-J. Li, Org. Lett. 2004, 6, 4997-4999;
20. d) Z. Li, C.-J. Li, J. Am. Chem. Soc. 2004, 126, 11 810-11 811;
21. e) Z. Li, C.-J. Li, Eur. J. Org. Chem. 2005, 3173-3176;
22. see also: f) S.-I. Murahashi, N. Komiya, H. Terai, T. Nakae, J. Am. Chem. Soc. 2003, 125, 15 312-15 313;
23. g) Y. Hatamoto, S. Sakaguchi, Y. Ishii, Org. Lett. 2004, 6, 4623-4625;
24. h) T. Yokota, M. Tani, S. Sakaguchi, Y. Ishii, J. Am. Chem. Soc. 2003, 125, 1476-1477;
25. i) J. Tsuji, H. Nagashima, Tetrahedron 1984, 40, 2699-2702;
26. j) B. DeBoef, S. J. Pastine, D. Sames, J. Am. Chem. Soc. 2004, 126, 6556-6557;
27. k) K. C. Nicolaou, R. E. Zipkin, N. A. Petasis, J. Am. Chem. Soc. 1982, 104, 5558-5560;
28. l) Z. Li, C.-J. Li, J. Am. Chem. Soc. 2006, 128, 56-57.
29. a) J. W. Blunt, B. R. Copp, M. H. G. Munro, P. T. Northcote, M. R. Prinsep, Nat. Prod. Rep. 2005, 22, 15-61;
30. b) V. M. Dembitsky, T. A. Gloriozova, V. V. Poroikov, Mini-Rev. Med. Chem. 2005, 5, 319-336;
31. c) T. L. Simmons, E. Andrianasolo, K. McPhail, P. Flatt, W. H. Gerwick, Mol. Cancer Ther. 2005, 4, 333-342;
32. ) D. J. Newman, G. M. Cragg, J. Nat. Prod. 2004, 67, 1216-1238;
33. e) L. Bongiorni, F. Pietra, Chem. Ind. 1996, (2), 54-58.
34. a) I. Kadota, Y. Yamamoto, Acc. Chem. Res. 2005, 38, 423-432;
35. b) M. Sasaki, H. Fuwa, Synlett 2004, 1851-1874;
36. c) L. F. Tietze, N. Rackelmann, Pure Appl. Chem. 2004, 76, 1967-1983;
37. d) E. Lee, Pure Appl. Chem. 1996, 68, 631-634;
38. e) G. M. Nicholas, A. J. Phillips, Nat. Prod. Rep. 2005, 22, 144-161.
39. For our early work on an ether-functionalization reaction, see: Y. Zhang, C.-J. Li, Tetrahedron Lett. 2004, 45, 7581-7584.
40. For representative reviews on indium catalyzed reactions, see: a) P. Cintas, Synlett 1995, 1087-1096;
41. b) C.-J. Li, Tetrahedron 1996, 52, 5643-5668;
42. c) J. A. Marshall, Chemtracts: Org. Chem. 1997, 10, 481;
43. d) I. Coldham, J. Chem. Soc. Perkin Trans. 1 1998, 1343-1364;
44. e) C.-J. Li, T.-H. Chan, Tetrahedron 1999, 55, 11 149-11 176;
45. f) K. K. Chauhan, C. G. Frost, J. Chem. Soc. Perkin Trans. 1 2000, 3015-3019;
46. g) B. C. Ranu, Eur. J. Org. Chem. 2000, 55, 2347-2356;
47. h) G. Babu, P. T. Perumal, Aldrichimica Acta 2000, 33, 16;
48. i) J. A. Marshall, Chem. Rev. 1996, 96, 31-48.
49. For recent reviews on copper-catalyzed reactions, see: a) I. P. Beletskaya, A. V. Cheprakov, Coord. Chem. Rev. 2004, 248, 2337-2364;
50. b) T. D. Nelson, R. D. Crouch, Org. React. 2004, 63, 265-555;
51. c) K. Kunz, U. Scholz, D. Ganzer, Synlett 2003, 2428-2439;
52. d) S. V. Ley, A. W. Thomas, Angew. Chem. 2003, 115, 5558-5607;
53. Angew. Chem. Int. Ed. 2003, 42, 5400-5449;
54. e) B. L. Feringa, R. Naasz, R. Imbos, L. A. Arnold in Modern Organocopper Chemistry (Ed.: N. Krause), Wiley-VCH, Weinheim, 2002, pp. 224-258;
55. f) J. Hassan, M. Sevignon, C. Gozzi, E. Schulz, M. Lemaire, Chem. Rev. 2002, 102, 1359-1470;
56. g) C. Hertweck, J. Prakt. Chem. 2000, 342, 316-321.
57. Such compounds exhibit a wide range of biological activities; for examples, see: a) R. E. Ziegert, J. Toraeng, K. Knepper, S. Bräse, J. Comb. Chem. 2005, 7, 147-169;
58. b) J. D. Hepworth, B. M. Heron, Prog. Heterocycl. Chem. 2003, 15, 360.
59. D. Hermeling, Ger. Offen. DE 4201544, A1 19930729, 1993, p. 5.
60. a) M. Nakamura, K. Endo, E. Nakamura, J. Am. Chem. Soc. 2003, 125, 13 002-13 003;
61. b) T. Pei, X. Wang, R. A. Widenhoefer, J. Am. Chem. Soc. 2003, 125, 648-649;
62. c) D. Yang, J. H. Li, Q. Gao, Y. L. Yan, Org. Lett. 2003, 5, 2869-2871;
63. d) J. J. Kennedy-Smith, S. T. Staben, F. D. Toste, J. Am. Chem. Soc. 2004, 126, 4526-4527;
64. e) X. Yao, C.-J. Li, J. Am. Chem. Soc. 2004, 126, 6884-6885;
65. f) R.-V. Nguyen, X. Yao, D. S. Bohle, C.-J. Li, Org. Lett. 2005, 7, 673-675.
66. H.-B. Zhang, L. Liu, Y.-J. Chen, D. Wang, C.-J. Li, Adv. Synth. Catal. 2006, 348, 229-235.