Stereodivergent synthesis of arylcyclopropylamines by sequential C-H borylation and Suzuki-Miyaura coupling

Angewandte Chemie - International Edition

Volumn 54, Issue 3, 2015, Pages 846-851

  Miyamura, Shin ^a   Araki, Misaho ^a   Suzuki, Takayoshi ^b,c   Yamaguchi, Junichiro ^a   Itami, Kenichiro ^a  

^a NAGOYA UNIVERSITY   (Japan)

^b KYOTO PREFECTURAL UNIVERSITY OF MEDICINE   (Japan)

^c JAPAN SCIENCE AND TECHNOLOGY AGENCY   (Japan)

Author keywords

Boron; C H activation; Cross coupling; Iridium; Small ring systems

Indexed keywords

ACTIVATION ANALYSIS; BORON; CARBON; CATALYSIS; IRIDIUM; SYNTHESIS (CHEMICAL);

C-H ACTIVATION; CIS-SELECTIVITY; CROSS-COUPLINGS; MATERIALS AND PRODUCTS; REACTION CONDITIONS; SMALL RING SYSTEMS; STEREODIVERGENT SYNTHESIS; SUZUKI-MIYAURA COUPLING;

CHEMICAL REACTIONS;

BORON; CARBON; CYCLOPROPANE DERIVATIVE; CYCLOPROPYLAMINE; HYDROGEN; IRIDIUM;

CATALYSIS; CHEMISTRY; CONFORMATION; STEREOISOMERISM; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

BORON; CARBON; CATALYSIS; CRYSTALLOGRAPHY, X-RAY; CYCLOPROPANES; HYDROGEN; IRIDIUM; MOLECULAR CONFORMATION; STEREOISOMERISM;

EID: 84920829729     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201409186     Document Type: Article

References (58)

1. a)W. A. Donaldson, Tetrahedron 2001, 57, 8589;
2. b) A. Reichelt, S. F. Martin, Acc. Chem. Res. 2006, 39, 433;
3. c) D. Y.-K. Chen, R. H. Pouwer, J.-A. Richard, Chem. Soc. Rev. 2012, 41, 4631.
4. a) J. Lindberg, S. Sigurdsson, S. Löwgren, H. O. Andersson, C. Sahlberg, R. Noréen, K. Fridborg, H. Zhang, T. Unge, Eur. J. Biochem. 2002, 269, 1670;
5. b) T.-Y. Tsai, T. Hsu, C.-T. Chen, J.-H. Cheng, T.-K. Yeh, X. Chen, C.-Y. Huang, C.-N. Chang, K.-C. Yeh, S.-H. Hsieh, C.-H. Chien, Y.-W. Chang, C.-H. Huang, Y.-W. Huang, C.-L. Huang, S.-H. Wu, M.-H. Wang, C.-T. Lu, Y.-S. Chao, W.-T. Jiaang, Bioorg. Med. Chem. 2009, 17, 2388;
6. c) T. Suzuki, N. Miyata, J. Med. Chem. 2011, 54, 8236;
7. d) D. Ogasawara, Y. Itoh, H. Tsumoto, T. Kakizawa, K. Mino, K. Fukuhara, H. Nakagawa, M. Hasegawa, R. Sasaki, T. Mizukami, N. Miyata, T. Suzuki, Angew. Chem. Int. Ed. 2013, 52, 8620.
8. b) M. Shiozaki, K. Maeda, T. Miura, Y. Ogoshi, J. Haas, A. M. Fryer, E. R. Laird, N. M. Littmann, S.W. Andrews, J. A. Josey, T. Mimura, Y. Shinozaki, H. Yoshiuchi, T. Inaba, Bioorg. Med. Chem. Lett. 2009, 19, 1575;
9. c) D. Ogasawara, T. Suzuki, K. Mino, R. Ueda, M. N. A. Khan, T. Matsubara, K. Koseki, M. Hasegawa, R. Sasaki, H. Nakagawa, T. Mizukami, N. Miyata, Bioorg. Med. Chem. 2011, 19, 3702.
10. a) J. Vallga˚rda, U. Appelberg, L. E. Arvidsson, S. Hjorth, B. E. Svensson, U. J. Hacksell, Med. Chem. 1996, 39, 1485;
11. b) C. A. Faler, M. M. Joullié, Org. Lett. 2007, 9, 1987.
12. a) J. Yamaguchi, A. D. Yamaguchi, K. Itami, Angew. Chem. Int. Ed. 2012, 51, 8960;
13. b) J. Wencel-Delord, F. Glorius, Nat. Chem. 2013, 5, 369;
14. c) H.-X. Dai, A. F. Stepan, M. S. Plummer, Y.-H. Zhang, J.-Q. Yu, J. Am. Chem. Soc. 2011, 133, 7222;
15. d) C. Meyer, D. Schepmann, S. Yanagisawa, J. Yamaguchi, V. Dal Col, E. Laurini, K. Itami, S. Pricl, B. Wünsch, J. Med. Chem. 2012, 55, 8047;
16. e) H. Sekizawa, K. Amaike, Y. Itoh, T. Suzuki, K. Itami, J. Yamaguchi, ACS Med. Chem. Lett. 2014, 5, 582;
17. f) T. Kang, Y. Kim, D. Lee, Z. Wang, S. Chang, J. Am. Chem. Soc. 2014, 136, 4141.
18. a) I. A. I. Mkhalid, J. H. Barnard, T. B. Marder, J. M. Murphy, J. F. Hartwig, Chem. Rev. 2010, 110, 890;
19. b) J. F. Hartwig, Acc. Chem. Res. 2012, 45, 864.
20. a) C. W. Liskey, J. F. Hartwig, J. Am. Chem. Soc. 2012, 134, 12422;
21. b) S. Kawamorita, T. Miyazaki, T. Iwai, H. Ohmiya, M. Sawamura, J. Am. Chem. Soc. 2012, 134, 12924;
22. c) T. Ohmura, T. Torigoe, M. Suginome, J. Am. Chem. Soc. 2012, 134, 17416;
23. d) S. Kawamorita, R. Murakami, T. Iwai, M. Sawamura, J. Am. Chem. Soc. 2013, 135, 2947;
24. e) S. H. Cho, J. F. Hartwig, J. Am. Chem. Soc. 2013, 135, 8157;
25. f) T. Mita, Y. Ikeda, K. Michigami, Y. Sato, Chem. Commun. 2013, 49, 5601;
26. g) T. Iwai, T. Harada, K. Hara, M. Sawamura, Angew. Chem. Int. Ed. 2013, 52, 12322;
27. h) T. Ohmura, T. Torigoe, M. Suginome, Chem. Commun. 2014, 50, 6333.
28. a) D. Imao, B. W. Glasspoole, V. S. Laberge, C. M. Crudden, J. Am. Chem. Soc. 2009, 131, 5024;
29. b) T. Ohmura, T. Awano, M. Suginome, J. Am. Chem. Soc. 2010, 132, 13191;
30. c) D. L. Sandrock, L. Jean-Gerard, C.-Y. Chen, S. D. Dreher, G. A. Molander, J. Am. Chem. Soc. 2010, 132, 17108;
31. d) J. C. H. Lee, R. McDonald, D. G. Hall, Nat. Chem. 2011, 3, 894;
32. e) J. Li, M. D. Burke, J. Am. Chem. Soc. 2011, 133, 13774;
33. f) T. Awano, T. Ohmura, M. Suginome, J. Am. Chem. Soc. 2011, 133, 20738;
34. g) G. A. Molander, S. R. Wisniewski, J. Am. Chem. Soc. 2012, 134, 16856;
35. h) B. M. Partridge, L. Chausset-Boissarie, M. Burns, A. P. Pulis, V. K. Aggarwal, Angew. Chem. Int. Ed. 2012, 51, 11795;
36. i) S. C. Matthew, B.W. Glasspoole, P. Eisenberger, C. M. Crudden, J. Am. Chem. Soc. 2014, 136, 5828.
37. a) J. E. A. Luithle, J. Pietruszka, J. Org. Chem. 1999, 64, 8287;
38. b) S. Löhr, A. de Meijere, Synlett 2001, 489;
39. c) M. Rubina, M. Rubin, V. Gevorgyan, J. Am. Chem. Soc. 2003, 125, 7198;
40. d) G.-H. Fang, Z.-J. Yan, M.-Z. Deng, Org. Lett. 2004, 6, 357;
41. e) J. Pietruszka, G. Solduga, Eur. J. Org. Chem. 2009, 5998.
42. a) P. E. Eaton, G. T. Cunkle,M. Gaetano, R. M. Martin, J. Am. Chem. Soc. 1987, 109, 948;
43. b) P. E. Eaton, R. G. Daniels, D. Casucci, G. T. Cunkle, P. Engel, J. Org. Chem. 1987, 52, 2100;
44. c) P. E. Eaton, C.-H. Lee, Y. Xiong, J. Am. Chem. Soc. 1989, 111, 8016;
45. d) M.-X. Zhang, P. E. Eaton, Angew. Chem. Int. Ed. 2002, 41, 2169;
46. e) P. E. Eaton, M.-X. Zhang, N. Komiya, C.-G. Yang, I. Steele, R. Gilardi, Synlett 2003, 1275;
47. f) M. Wasa, K. M. Engle, D. W. Lin, E. J. Yoo, J.-Q. Yu, J. Am. Chem. Soc. 2011, 133, 19598.
48. C.W. Liskey, J. F. Hartwig, J. Am. Chem. Soc. 2013, 135, 3375.
49. A. Ros, R. Fernandez, J. M. Lassaletta, Chem. Soc. Rev. 2014, 43, 3229.
50. R. Murakami, K. Tsunoda, T. Iwai, M. Sawamura, Chem. Eur. J. 2014, 20, 13127.
51. Q. Li, C.W. Liskey, J. F. Hartwig, J. Am. Chem. Soc. 2014, 136, 8755.
52. P. C. Roosen, V. A. Kallepalli, B. Chattopadhyay, D. A. Singleton, R. E. Maleczka Jr.,M. R. Smith III, J. Am. Chem. Soc. 2012, 134, 11350.
53. E. M. Simmons, J. F. Hartwig, Nature 2012, 483, 70.
54. The yield of isolated 2a was somewhat lower than that of the yield determined by NMR spectroscopy (before isolation). This difference is due to the difficulty in separating 2a from a starting material 1a by simple silica-gel column chromatography.
55. For the effect of other reaction parameters, see the Supporting Information for details.
56. For details of optimization, see the Supporting Information.
57. The reaction conditions reported by Suginome et al. (Ref [8b]) did not work in our case.
58. Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data-request/cif.