Stereospecific nickel-catalyzed cross-coupling reactions of alkyl grignard reagents and identification of selective anti-breast-cancer agents

Angewandte Chemie - International Edition

Volumn 53, Issue 9, 2014, Pages 2422-2427

  Yonova, Ivelina M ^a   Johnson, A George ^a   Osborne, Charlotte A ^a   Moore, Curtis E ^b   Morrissette, Naomi S ^a   Jarvo, Elizabeth R ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

^b UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

alkyl Grignard reagents; breast cancer; enantiospecificity; Kumada coupling; nickel

Indexed keywords

ALKANE; ANTINEOPLASTIC AGENT; AROMATIC HYDROCARBON; DYES, REAGENTS, INDICATORS, MARKERS AND BUFFERS; NICKEL;

ALKYL GRIGNARD REAGENTS; ARTICLE; BREAST CANCER; BREAST TUMOR; CATALYSIS; CHEMISTRY; ENANTIOSPECIFICITY; FEMALE; HUMAN; KUMADA COUPLING; STEREOISOMERISM; SYNTHESIS; TUMOR CELL LINE;

ALKYL GRIGNARD REAGENTS; BREAST CANCER; ENANTIOSPECIFICITY; KUMADA COUPLING; NICKEL;

ALKANES; ANTINEOPLASTIC AGENTS; BREAST NEOPLASMS; CATALYSIS; CELL LINE, TUMOR; FEMALE; HUMANS; HYDROCARBONS, AROMATIC; INDICATORS AND REAGENTS; NICKEL; STEREOISOMERISM;

EID: 84894436223     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201308666     Document Type: Article

References (52)

1. E. C. Swift, E. R. Jarvo, Tetrahedron 2013, 69, 5799-5817
2. B. L. H. Taylor, E. R. Jarvo, Synlett 2011, 2761-2765
3. R. Jana, T. P. Pathak, M. S. Sigman, Chem. Rev. 2011, 111, 1417-1492
4. F. Glorius, Angew. Chem. 2008, 120, 8474-8476
5. Angew. Chem. Int. Ed. 2008, 47, 8347-8349.
6. For a lead reference of stereoconvergent alkyl-alkyl cross-coupling, see:, C. J. Cordier, R. J. Lundgren, G. C. Fu, J. Am. Chem. Soc. 2013, 135, 10946-10949.
7. B. L. H. Taylor, E. C. Swift, J. D. Waetzig, E. R. Jarvo, J. Am. Chem. Soc. 2011, 133, 389-391
8. M. A. Greene, I. M. Yonova, F. J. Williams, E. R. Jarvo, Org. Lett. 2012, 14, 4293-4296.
9. For stereospecific Negishi couplings, see:, H. M. Wisniewska, E. C. Swift, E. R. Jarvo, J. Am. Chem. Soc. 2013, 135, 9083-9090.
10. B. L. H. Taylor, M. R. Harris, E. R. Jarvo, Angew. Chem. 2012, 124, 7910-7913
11. Angew. Chem. Int. Ed. 2012, 51, 7790-7793; for stereospecific Suzuki couplings of aryl boronic esters, see
12. M. R. Harris, L. E. Hanna, M. A. Greene, C. E. Moore, E. R. Jarvo, J. Am. Chem. Soc. 2013, 135, 3303-3306
13. Q. Zhou, H. D. Srinivas, S. Dasgupta, M. P. Watson, J. Am. Chem. Soc. 2013, 135, 3307-3310.
14. We hypothesize that a weighing error was responsible for the high variability in these small scale reactions; see:, M. Wernerova, T. Hudlicky, Synlett 2010, 2701-2707.
15. K. J. Fisher, E. C. Alyea, Polyhedron 1989, 8, 13-15; for a similar observation, see
16. K.-i. Yamashita, H. Takeda, T. Kashiwabara, R. Hua, S. Shimada, M. Tanaka, Tetrahedron Lett. 2007, 48, 6655-6659.
17. B. L. H. Taylor, Development of Nickel-Catalyzed Stereospecific Cross-Coupling Reactions, University of California, Irvine, 2012, Order No. 3540398.
18. Ann Arbor: ProQuest. Web. 17 July 2013.
19. S. I. Murahashi, Y. Taniguchi, Y. Imada, Y. Tanigawa, J. Org. Chem. 1989, 54, 3292-3303
20. K. L. Granberg, J. E. Bäckvall, J. Am. Chem. Soc. 1992, 114, 6858-6863.
21. J.-Y. Legros, M. Toffano, J.-C. Fiaud, Tetrahedron 1995, 51, 3235-3246.
22. This mechanism was proposed and discounted in favor of a radical oxidative addition reaction to rationalize stereoablative reactions of benzylic bromides with nickel complexes; see:, J. K. Stille, A. B. Cowell, J. Organomet. Chem. 1977, 124, 253-261.
23. E. J. Corey, C. J. Helal, Angew. Chem. 1998, 110, 2092-2118
24. Angew. Chem. Int. Ed. 1998, 37, 1986-2012
25. "Reductions":, J. J. Li, C. Limberakis, D. A. Pflum, in Modern Organic Synthesis in the Laboratory: A Collection of Standard Experimental Procedures, Oxford University Press, New York, 2007, pp. 96-97.
26. R. Noyori, M. Kitamura, Angew. Chem. 1991, 103, 34-55
27. Angew. Chem. Int. Ed. Engl. 1991, 30, 49-69
28. F.-Y. Zhang, C.-W. Yip, C. Rong, A. S. C. Chan, Tetrahedron: Asymmetry 1997, 8, 585-589.
29. C. Bolm, J. Rudolph, J. Am. Chem. Soc. 2002, 124, 14850-14851
30. A. L. Braga, M. W. Paixao, B. Westermann, P. H. Schneider, L. A. Wessjohann, J. Org. Chem. 2008, 73, 2879-2882.
31. The competing enantiomer conversion method can be used to assign the absolute configuration of secondary alcohols; see:, A. J. Wagner, S. D. Rychnovsky, J. Org. Chem. 2013, 78, 4594-4598.
32. as ligands for nuclear receptors, see:, M. Kainuma, J.-i. Kasuga, S. Hosoda, K.-i. Wakabayashi, A. Tanatani, K. Nagasawa, H. Miyachi, M. Makishima, Y. Hashimoto, Bioorg. Med. Chem. Lett. 2006, 16, 3213-3218
33. as combretastatin analogues for colon cancer, see:, S. Messaoudi, A. Hamze, O. Provot, B. Tréguier, J. Rodrigo De Losada, J. Bignon, J.-M. Liu, J. Wdzieczak-Bakala, S. Thoret, J. Dubois, J.-D. Brion, M. Alami, ChemMedChem 2011, 6, 488-497
34. prostate cancer:, Q. Z. Hu, L. N. Yin, C. Jagusch, U. E. Hille, R. W. Hartmann, J. Med. Chem. 2010, 53, 5049-5053
35. diabetes:, R. M. Kim, E. R. Parmee, Q. Tan, C. Yang, A. R. Lins, U.S. Patent 12/227,030, May 11, 2007.
36. T. P. Pathak, K. M. Gligorich, B. E. Welm, M. S. Sigman, J. Am. Chem. Soc. 2010, 132, 7870-7871
37. T. P. Pathak, J. G. Osiak, R. M. Vaden, B. E. Welm, M. S. Sigman, Tetrahedron 2012, 68, 5203-5208.
38. A. Lõpez-Pérez, J. Adrio, J. C. Carretero, Org. Lett. 2009, 11, 5514-5517
39. D. Imao, B. W. Glasspoole, V. S. Laberge, C. M. Crudden, J. Am. Chem. Soc. 2009, 131, 5024-5025
40. J. Li, M. D. Burke, J. Am. Chem. Soc. 2011, 133, 13774-13777
41. P. Maity, D. M. Shacklady-McAtee, G. P. A. Yap, E. R. Sirianni, M. P. Watson, J. Am. Chem. Soc. 2013, 135, 280-285.
42. V. Saini, L. Liao, Q. Wang, R. Jana, M. S. Sigman, Org. Lett. 2013, 15, 5008-5011
43. X. Wang, A. Guram, S. Caille, J. Hu, J. P. Preston, M. Ronk, S. Walker, Org. Lett. 2011, 13, 1881-1883
44. T. C. Fessard, S. P. Andrews, H. Motoyoshi, E. M. Carreira, Angew. Chem. 2007, 119, 9492-9495
45. Angew. Chem. Int. Ed. 2007, 46, 9331-9334.
46. J. K. Kochi, Pure Appl. Chem. 1980, 52, 571-605
47. G. D. Jones, J. L. Martin, C. McFarland, O. R. Allen, R. E. Hall, A. D. Haley, R. J. Brandon, T. Konovalova, P. J. Desrochers, P. Pulay, D. A. Vicic, J. Am. Chem. Soc. 2006, 128, 13175-13183
48. J. Choi, G. C. Fu, J. Am. Chem. Soc. 2012, 134, 9102-9105
49. X. Lin, D. L. Phillips, J. Org. Chem. 2008, 73, 3680-3688; for evidence of Ni-C bond homolysis after a polar oxidative addition, see
50. D. K. Nielsen, C.-Y. Huang, A. G. Doyle, J. Am. Chem. Soc. 2013, 135, 13605-13609.
51. A. Howell, Endocr.-Relat. Cancer 2006, 13, 689-706
52. A. E. Wakeling, M. Dukes, J. Bowler, Cancer Res. 1991, 51, 3867-3873