Cross-coupling reaction between alcohols through sp3 C-H activation catalyzed by a ruthenium/lewis acid system

Chemistry - A European Journal

Volumn 14, Issue 33, 2008, Pages 10201-10205

  Zhang, Shu Yu ^a   Tu, Yong Qiang ^a   Fan, Chun An ^a   Jiang, Yi Jun ^a   Shi, Lei ^a   Cao, Ke ^a   Zhang, En ^a  

^a LANZHOU UNIVERSITY   (China)

Author keywords

Alcohols; C C coupling; C H activation; Cross coupling; Ruthenium

Indexed keywords

ACTIVATION ANALYSIS; CATALYSIS; CATALYSTS; ETHANOL; METAL RECOVERY; OLEFINS; ORGANIC SOLVENTS; RHODIUM COMPOUNDS; RUTHENIUM; STEREOSELECTIVITY; TRANSITION METALS;

ACID SYSTEMS; C-C COUPLING; C-H ACTIVATION; C-H ACTIVATIONS; COUPLING REACTIONS; CROSS COUPLINGS; CROSS-COUPLING; DIPHENYLETHANOL; DIPHENYLETHENE; FUNCTIONALIZED; H BONDS; LEWIS ACIDS; PRIMARY ALCOHOLS; TERTIARY ALCOHOLS;

ACIDS;

EID: 56349096338     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.200801317     Document Type: Article

References (54)

1. For recent selected examples of transition-metal-catalyzed C-C cross-coupling between ketones and alcohols, see: a) C. S. Cho, B. T. Kim, M. J. Lee, T.-J. Kim, S. C. Shim, Angew. Chem. 2001, 113, 984-986;
2. Angew. Chem. Int. Ed. 2001, 40, 958-960;
3. b) C. S. Cho, B. T. Kim, T.-J. Kim, S. C. Shim, J. Org. Chem. 2001, 66, 9020-9022;
4. c) Y. Nishibayashi, I. Wakiji, Y. Ishii, S. Uemura, M. Hidai, J. Am. Chem. Soc. 2001, 123, 3393-3394;
5. d) M. G. Edwards, J. M. J. Williams, Angew. Chem. 2002, 114, 4934-4937;
6. Angew. Chem. Int. Ed. 2002, 41, 4740-4743;
7. e) K. Taguchi, H. Nakagawa, T. Hirabayashi, S. Sakaguchi, Y. Ishii, J. Am. Chem. Soc. 2004, 126, 72-73;
8. f) M. G. Edwards, R. F. R. Jazzar, B. M. Panie, D. J. Shermer, M. K. Whittlesey, J. M. J. Williams, D.D. Edney, Chem. Commun. 2004, 90-91;
9. g) M.S. Kwon, N. Kim, S. H. Seo, I. S. Park, R. K. Cheedrala, J. Park, Angew. Chem. 2005, 117, 7073-7075;
10. Angew. Chem. Int. Ed. 2005, 44, 6913-6915;
11. h) G. Onodera, Y. Nishibayashi, S. Uemura, Angew. Chem. 2006, 118, 3903-3906;
12. Angew. Chem. Int. Ed. 2006, 45, 3819-3822;
13. i) Y. M. A. Yamada, Y. Uozumi, Org. Lett. 2006, 8, 1375-1378;
14. j) P. J. Black, M. G. Edwards, J. M. J. Williams, Eur. J. Org. Chem. 2006, 4367-4378;
15. k) P. J. Black, G. Cami-Kobeci, M. G. Edwards, P. A. Slatford, M.K. Whittlesey, J.M.J. Williams, Org. Biomol. Chem. 2006, 4, 116-125.
16. For recent examples of transition-metal-catalyzed C-C cross-coupling between alkenes and alcohols by oxidation-hydroacylation-reduction sequences, see: a) C.-H. Jun, C.-W. Huh, S.-X Na, Angew. Chem. 1998, 110, 150-152;
17. Angew. Chem. Int. Ed. 1998, 37, 145-147;
18. b) D.-Y Lee, C. W. Moon, C.-H. Jun J. Org. Chem. 2002, 67, 3945-3948;
19. c) D.-H Chang, D.-Y Lee, B.-S. Hong, J.-H. Choi, C.-H. Jun, J. Am. Chem. Soc. 2004, 126, 424-425;
20. d) D.-W. Kim, S.-G. Lim, C.-H. Jun, Org. Lett. 2006, 8, 2937-2940.
21. For recent examples of transition-metal-catalyzed C-C cross-coupling between alkenes and alcohols by transfer hydrogenative coupling, see: a) J. F. Bower, E. Skucas, R. L. Patman, M. J. Krische, J. Am. Chem. Soc. 2007, 129, 15134-15135;
22. b) J. F. Bower, R. L. Patman, M.J. Krische, Org. Lett. 2008, 10, 1033-1035;
23. c) F. Shibahara, J. F. Bower, M. J. Krische, J. Am. Chem. Soc. 2008, 130, 6338-6339;
24. d) I. S. Kim, M. Y. Ngai, M.J. Krische, J. Am. Chem. Soc. 2008, 130, 6340-6341.
25. For Rh- and Pd-catalyzed C-C cross-coupling between alkenes and alcohols by C-H activation, see: a) L. Shi, Y.-Q. Tu, M. Wang, F.-M. Zhang, C.-A. Fan, Y.-M. Zhao, W.-J. Xia, J. Am. Chem. Soc. 2005, 127, 10836-10837;
26. b) Y.-X. Jiang, Y.-Q. Tu, E. Zhang, S.-Y. Zhang, K. Cao, L. Shi, Adv. Synth. Catal. 2008, 350, 552-556.
27. For C-C cross-coupling of alkenes with supercritical alcohols, see: T. Kamitanaka, T. Hikida, S. Hayashi, N. Kishida, T. Matsuda, T. Harada, Tetrahedron Lett. 2007, 48, 8460-8463, and references therein.
28. For the transition-metal-catalyzed C-C cross-coupling between alcohols by the hydrogen autotransfer process, see : a) C. S. Cho, B. T. Kim, H.-S. Kim, T.-J. Kim, S. C. Shim, Organometallics 2003, 22, 3608-3610;
29. b) K.-i. Fujita, C. Asai, T. Yamaguchi, F. Hanasaka, R. Yamaguchi, Org. Lett. 2005, 7, 4017-4019;
30. c) G. R. A. Adair, J. M. J. Williams, Tetrahedron Lett. 2005, 46, 8233-8235;
31. d) C. S. Cho, W. X. Ren, S. C. Shim, Bull. Korean Chem. Soc. 2005, 26, 1611-1613;
32. e) R. Martinez, D. J. Ramón, M. Yus, Tetrahedron 2006, 62, 8982-8987.
33. a) B. M. Trost, Science 1991, 254,1471-1477;
34. b) R. A. Sheldon, Pure Appl. Chem. 2000, 72, 1233-1246;
35. c) B. M. Trost, Acc. Chem. Res. 2002, 35, 695-705.
36. For some reviews of ruthenium-catalyzed C-C coupling, see: a) B. M. Trost, F. D. Toste, A. B. Pinkerton, Chem. Rev. 2001, 101, 2067-2096;
37. b)T. Kondo, T.-a. Mitsudo, Curr. Org. Chem. 2002, 6, 1163-1193;
38. c) S. Dérien, F. Monnier, P. H. Dixneuf, Top. Organomet. Chem. 2004, 11, 1-44;
39. d) Ruthenium in Organic Synthesis (Ed.: S.-I. Murahashi), Wiley-VCH, Weinheim, 2004.
40. For recent reviews of hydrogen autotransfer processes, see: A. G. Guillena, D.J. Ramón, M. Yus, Angew. Chem. 2007, 119, 2410-2416;
41. Angew. Chem. Int. Ed. 2007, 46, 2358-2364, and references therein.
42. For the details on the reaction condition, see Supporting Information.
43. For the determination of the relative configuration, see Scheme 1 in the Supporting Information.
44. For selected reviews of hydroacylation, see: a) B. Bosnich, Ace. Chem. Res. 1998, 31, 667-674;
45. b) M. Tanaka, K. Sakai, H. Suemune, Curr. Org. Chem. 2003, 7, 353-367;
46. c) G. C. Fu in Modern Rhodium-Catalyzed Organic Reactions (Ed.: P.A. Evans), Wiley-VCH, New York, 2005, pp. 79-91;
47. d) Y. J. Park, J.-W. Park, C.-H. Jun, Acc. Chem. Res. 2008, 41, 222-234, and references therein.
48. For the comparison of different pathway in deuterium experiment, see Scheme 2 in the Supporting Information.
49. 3 C-H bond activation adjacent to oxygen and the subsequent C-C bond formation reactions, see: a) Y. Lin, D. Ma; X. Lu, Tetrahedron Lett. 1987, 28, 3249-3252;
50. b) S. J. Pastine, K. M. McQuaid, D. Sames, J. Am. Chem. Soc. 2005, 127, 12180-12181;
51. c) Y. Zhang, C.-J. Li, Angew. Chem,. 2006, 118, 1983-1986;
52. Angew. Chem. Int. Ed. 2006, 45, 1949-1952;
53. d) Y. Zhang, C.-J. Li, J. Am. Chem. Soc. 2006, 128, 4242-4243.
54. For the preferred conformation of the radical intermediate D, see Scheme 3 in the Supporting Information.