Copper-Catalyzed Reductive Cross-Coupling of Nonactivated Alkyl Tosylates and Mesylates with Alkyl and Aryl Bromides

Chemistry - A European Journal

Volumn 20, Issue 47, 2014, Pages 15334-15338

  Liu, Jing Hui ^a,b,c   Yang, Chu Ting ^a,b,c   Lu, Xiao Yu ^a,b,c   Zhang, Zhen Qi ^a,b,c   Xu, Ling ^a,b,c   Cui, Mian ^a,b,c   Lu, Xi ^a,b,c   Xiao, Bin ^a,b,c   Fu, Yao ^a,b,c   Liu, Lei ^a,b,c  

^a UNIVERSITY OF SCIENCE AND TECHNOLOGY OF CHINA   (China)

^b LANZHOU INSTITUTE OF CHEMICAL PHYSICS   (China)

^c TSINGHUA UNIVERSITY   (China)

Author keywords

C=C bond formation; catalysis; copper; cross coupling; cyclization

Indexed keywords

CATALYSIS; COPPER; COST EFFECTIVENESS; CYCLIZATION; METAL HALIDES; SULFUR COMPOUNDS;

ARYL BROMIDES; BOND FORMATION; COPPER CATALYZED; COST EFFECTIVE; CROSS COUPLING REACTIONS; CROSS-COUPLINGS; PRACTICAL METHOD; STEREOCONTROL;

CHEMICAL REACTIONS;

EID: 84941091154     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.201405223     Document Type: Article

References (59)

1. Metal-Catalyzed Cross-Coupling Reactions, Second Edition (Eds: A. de Meijere, F. Diederich), WILEY-VCH, Weinheim, 2008;
2. Transition Metals for Organic Synthsis: Building Blocks, and, Fine Chemicals, Second Revised, and, Enlarged Edition (Eds: M. Beller, C. Bolm), WILEY-VCH, Weinheim, 2008.
3. A. C. Frisch, M. Beller, Angew. Chem. Int. Ed. 2005, 44, 674-688;
4. Angew. Chem. 2005, 117, 680-695;
5. J. Terao, N. Kambe, Acc. Chem. Res. 2008, 41, 1545-1554;
6. A. Rudolph, M. Lautens, Angew. Chem. Int. Ed. 2009, 48, 2656-2670;
7. Angew. Chem. 2009, 121, 2694-2708;
8. X. Hu, Chem. Sci. 2011, 2, 1867-1886;
9. R. Jana, T. P. Pathak, M. S. Sigman, Chem. Rev. 2011, 111, 1417-1492;
10. N. Kambe, T. Iwasaki, J. Terao, Chem. Soc. Rev. 2011, 40, 4937-4947;
11. C. E. I. Knappke, A. J. von Wangelin, Chem. Soc. Rev. 2011, 40, 4948-4962.
12. P. Knochel, in Handbook of Functionalized Organometallics: Applications in Synthesis Wiley-VCH, Weinheim, 2005; for recent advances on the preparation of functionalized organometallic reagents, see:
13. B. Haag, M. Mosrin, H. Ila, V. Malakhov, P. Knochel, Angew. Chem. Int. Ed. 2011, 50, 9794-9824;
14. Angew. Chem. 2011, 123, 9968-9999;
15. G. Monzõn, I. Tirotta, P. Knochel, Angew. Chem. Int. Ed. 2012, 51, 10624-10627;
16. Angew. Chem. 2012, 124, 10776-10779;
17. C. Sämann, M. A. Schade, S. Yamada, P. Knochel, Angew. Chem. Int. Ed. 2013, 52, 9495-9499;
18. Angew. Chem. 2013, 125, 9673-9677.
19. For a recent review on reductive cross-coupling reactions between two electrophiles, see:, C. E. I. Knappke, S. Grupe, D. Gärtner, M. Corpet, C. Gosmini, A. J. von Wangelin, Chem. Eur. J. 2014, 20, 6828-6842.
20. M. Amatore, C. Gosmini, Angew. Chem. Int. Ed. 2008, 47, 2089-2092;
21. Angew. Chem. 2008, 120, 2119-2122;
22. A. Moncomble, P. Le Floch, C. Gosmini, Chem. Eur. J. 2009, 15, 4770-4774;
23. M. Amatore, C. Gosmini, Chem. Eur. J. 2010, 16, 5848-5852.
24. A. Krasovskiy, C. Duplais, B. H. Lipshutz, J. Am. Chem. Soc. 2009, 131, 15592-15593;
25. A. Krasovskiy, C. Duplais, B. H. Lipshutz, Org. Lett. 2010, 12, 4742-4744.
26. W. M. Czaplik, M. Mayer, A. J. von Wangelin, Angew. Chem. Int. Ed. 2009, 48, 607-610;
27. Angew. Chem. 2009, 121, 616-620.
28. D. A. Everson, R. Shrestha, D. J. Weix, J. Am. Chem. Soc. 2010, 132, 920-921;
29. D. A. Everson, B. A. Jones, D. J. Weix, J. Am. Chem. Soc. 2012, 134, 6146-6159;
30. S. Wang, Q. Qian, H. Gong, Org. Lett. 2012, 14, 3352-3355;
31. S. Biswas, D. J. Weix, J. Am. Chem. Soc. 2013, 135, 16192-16197;
32. H. Xu, C. Zhao, Q. Qian, W. Deng, H. Gong, Chem. Sci. 2013, 4, 4022-4029;
33. Y. Zhao, D. J. Weix, J. Am. Chem. Soc. 2014, 136, 48-51.
34. X. Qian, A. Auffrant, A. Felouat, C. Gosmini, Angew. Chem. Int. Ed. 2011, 50, 10402-10405;
35. Angew. Chem. 2011, 123, 10586-10589;
36. P. Gomes, C. Gosmini, J. Périchon, Org. Lett. 2003, 5, 1043-1045;
37. J. Terao, H. Watabe, H. Watanabe, N. Kambe, Adv. Synth. Catal. 2004, 346, 1674-1678.
38. S. M. Goldup, D. A. Leigh, R. T. McBurney, P. R. McGonigal, A. Plant, Chem. Sci. 2010, 1, 383-386;
39. M. R. Prinsell, D. A. Everson, D. J. Weix, Chem. Commun. 2010, 46, 5743-5745.
40. J. Terao, A. Lkumi, H. Kuniyasu, N. Kambe, J. Am. Chem. Soc. 2003, 125, 5646-5647;
41. J. Terao, H. Todo, S. A. Begum, H. Kuniyasu, N. Kambe, Angew. Chem. Int. Ed. 2007, 46, 2086-2089;
42. Angew. Chem. 2007, 119, 2132-2135;
43. C.-T. Yang, Z.-Q. Zhang, Y.-C. Liu, L. Liu, Angew. Chem. Int. Ed. 2011, 50, 3904-3907;
44. Angew. Chem. 2011, 123, 3990-3993;
45. P. Ren, L. Salihu, R. Scopelliti, X. Hu, Org. Lett. 2012, 14, 1748-1751;
46. C.-T. Yang, Z.-Q. Zhang, H. Tajuddin, C.-C. Wu, J. Liang, J.-H. Liu, Y. Fu, M. Czyzewska, P. G. Steel, T. B. Marder, L. Liu, Angew. Chem. Int. Ed. 2012, 51, 528-532;
47. Angew. Chem. 2012, 124, 543-547;
48. P. Ren, L.-A. Stern, X. Hu, Angew. Chem. Int. Ed. 2012, 51, 9110-9113;
49. Angew. Chem. 2012, 124, 9244-9247;
50. R. Shen, T. Iwasaki, J. Terao, N. Kambe, Chem. Commun. 2012, 48, 9313-9315;
51. C.-T. Yang, Z.-Q. Zhang, J. Liang, J.-H. Liu, X.-Y. Lu, H.-H. Chen, L. Liu, J. Am. Chem. Soc. 2012, 134, 11124-11127.
52. Even for Cu-catalyzed reductive cross-coupling of activated electrophiles there is only one example:, E. Erdik, M. Koçolu, Tetrahedron Lett. 2007, 48, 4211-4214.
53. H. Kim, C. Lee, Org. Lett. 2011, 13, 2050-2053;
54. C.-H. Yan, Y. Peng, X.-B. Xu, Y.-W. Wang, Chem. Eur. J. 2012, 18, 6039-6048. For Pd-catalyzed reductive cyclization:
55. H. Liu, J. Wei, Z. Qiao, Y. Fu, X. Jiang, Chem. Eur. J. 2014, 86, 1-7.
56. E. Shirakawa, D. Ikeda, S. Masui, M. Yoshida, T. Hayashi, J. Am. Chem. Soc. 2012, 134, 272-279.
57. Functionalized aryl Grignard reagents bearing a leaving group (e.g. halide or tosylate) are difficult to synthesize by the reaction of aryl halides with Mg. They can only be prepared by reacting iPrMgCl with aryl iodides at -30 C. For a recent report, see:, F. F. Kneisel, Y. Monguchi, K. M. Knapp, H. Zipse, P. Knochel, Tetrahedron Lett. 2002, 43, 4875-4879.
58. J. E. Frampton, Drugs 2009, 69, 2463-2476;
59. M. Lachia, C. J. Moody, Nat. Prod. Rep. 2008, 25, 227-253.