Copper-catalyzed aminoboration and hydroamination of alkenes with electrophilic amination reagents

Pure and Applied Chemistry

Volumn 86, Issue 3, 2014, Pages 291-297

  Hirano, Koji ^a   Miura, Masahiro ^a  

^a OSAKA UNIVERSITY   (Japan)

Author keywords

amino derivatives; aminoboration; asymmetric catalysis; boron; copper; hydroamination; umpolung

Indexed keywords

AMINES; BORON; CATALYSIS; COPPER; ENANTIOSELECTIVITY; HYDROCARBONS; REACTION KINETICS; REGIOSELECTIVITY; STYRENE; SYNTHESIS (CHEMICAL);

AMINOBORATION; ASYMMETRIC CATALYSIS; BIPHOSPHINE LIGANDS; ELECTROPHILIC AMINATION; HYDROAMINATIONS; POLYMETHYLHYDROSILOXANES; REGIOSELECTIVE HYDROAMINATION; UMPOLUNG;

AMINATION;

EID: 84896273664     PISSN: 00334545     EISSN: 13653075     Source Type: Journal    
DOI: 10.1515/pac-2014-5004     Document Type: Conference Paper

References (69)

1. R. Hili, A. K. Yudin. Nat. Chem. Biol. 2, 284 (2006);
2. A. Ricci. Amino Group Chemistry: From Synthesis to the Life Sciences, Wiley-VCH, Weinheim (2007).
3. For reviews, see: (a) E. Erdik, M. Ay. Chem. Rev. 89, 1947 (1989);
4. K. Narasaka M. Kitamura. Eur. J. Org. Chem. 21 4505 2005
5. E. Ciganek. Org. React. 72, 1 (2009);
6. T. J. Barker, E. R. Jarbo. Synthesis 3954 (2011).
7. T. Kawano, K. Hirano, T. Satoh, M. Miura. J. Am. Chem. Soc. 132, 6900 (2010);
8. K. Hirano, T. Satoh, M. Miura. Org. Lett. 13, 2395 (2011);
9. N. Matsuda, K. Hirano, T. Satoh, M. Miura. Org. Lett. 13, 2869 (2011);
10. N. Matsuda, K. Hirano, T. Satoh, M. Miura. J. Org. Chem. 77, 617 (2012);
11. N. Matsuda, K. Hirano, T. Satoh, M. Miura. Angew. Chem., Int. Ed. 51, 3642 (2012);
12. N. Matsuda, K. Hirano, T. Satoh, M. Miura. Synthesis 44, 1792 (2012);
13. N. Matsuda, K. Hirano, T. Satoh, M. Miura. Angew. Chem., Int. Ed. 51, 11827 (2012);
14. Y. Miki, K. Hirano, T. Satoh, M. Miura. Org. Lett. 15, 172 (2013);
15. R. Sakae, K. Hirano, T. Satoh, M. Miura. Chem. Lett. 42, 1128 (2013). http:/dx/doi.org/10.1246/cl.130485.
16. For recent examples, see: (a) A. M. Berman, J. S. Johnson. J. Am. Chem. Soc. 126, 5680 (2004);
17. S. Liu L. S. Liebeskind. J. Am. Chem. Soc. 130 6918 2008);
18. C. He, C. Chen, J. Cheng, C. Liu, W. Liu, Q. Li, A. Lei. Angew. Chem., Int. Ed. 47, 6414 (2008);
19. T. J. Barker, E. R. Jarvo. J. Am. Chem. Soc. 131, 15598 (2009);
20. T. Hatakeyama, Y. Yoshimoto, S. K. Ghorai, M. Nakamura. Org. Lett. 12, 1516 (2010);
21. C. Grohmann, H. Wang, F. Glorius. Org. Lett. 14, 656 (2012);
22. Q. Xiao, L. Tian, R. Tan, Y. Xia, D. Qiu, Y. Zhang, J. Wang. Org. Lett. 14, 4230 (2012);
23. R. P. Rucker, A. M. Whittaker, H. Dang, G. Lalic. J. Am. Chem. Soc. 134, 6571 (2012);
24. S. N. Mlynarski, A. S. Karns, J. P. Morken. J. Am. Chem. Soc. 134, 16449 (2012);
25. C. Zhu, G. Li, D. H. Ess, J. R. Falck, L. Kürti. J. Am. Chem. Soc. 134, 18253 (2012);
26. T. Miura, M. Morimoto, M. Murakami. Org. Lett. 14, 5214 (2012);
27. X. Qian, Z. Yu, A. Auffrant, C. Gosmini. Chem.-Eur. J. 19, 6225 (2013).
28. N. Matsuda, K. Hirano, T. Satoh, M. Miura. J. Am. Chem. Soc. 135, 4934 (2013).
29. Y. Miki, K. Hirano, T. Satoh, M. Miura. Angew. Chem., Int. Ed. 52, 10830 (2013). http:/dx/doi.org/10.1002/anie.201304365.
30. A. Pelter, K. Smith, H. C. Brown. Borane Reagents, Academic Press, London (1988);
31. N. Miyaura, A. Suzuki. Chem. Rev. 95, 2457 (1995);
32. M. Davison, A. K. Hughes, T. B. Marder, K. Wade. Contemporary Boron Chemistry, RSC, Cambridge, UK (2000);
33. D. G. Hall (Ed.). Boronic Acids, 2nd ed., Wiley-VCH, Weinheim (2011).
34. M. Suginome, T. Ohmura. In Boronic Acids, 2nd ed., D. G. Hall (Ed.), p. 171, Wiley-VCH, Weinheim (2011).
35. Y. Lee, A. H. Hoveyda. J. Am. Chem. Soc. 131, 3160 (2009);
36. Y. Sasaki, C. Zhong, M. Sawamura, H. Ito. J. Am. Chem. Soc. 132, 1226 (2010);
37. Y. Sasaki, Y. Horita, C. Zhong, M. Sawamura, H. Ito. Angew. Chem., Int. Ed. 50 2778 2011)
38. R. Corberán, N. W. Mszar, A. H. Hoveyda. Angew. Chem., Int. Ed. 50, 7079 (2011);
39. H. Jang, A. R. Zhugralin, Y. Lee, A. H. Hoveyda. J. Am. Chem. Soc. 133, 7859 (2011);
40. H.-Y. Jung, J. Yun. Org. Lett. 14, 2606 (2012);
41. J. K. Park, B. A. Ondrusek, D. T. McQuade. Org. Lett. 14, 4790 (2012);
42. K. Semba, T. Fujihara, J. Terao, Y. Tsuji. Chem.-Eur. J. 18, 4179 (2012);
43. W. Yuan, S. Ma. Org. Biomol. Chem. 10, 7266 (2012);
44. A. L. Moure, R. G. Arrayás, D. J. Cárdenas, I. Alonso, J. C. Carretero. J. Am. Chem. Soc. 134, 7219 (2012);
45. W. Yuan, S. Ma. Adv. Synth. Catal. 354, 1867 (2012).
46. The Cu-catalyzed carboboration and stannylboration of alkynes and alkenes based on a similar concept were reported. See: (a) L. Zhang, J. Cheng, B. Carry, Z. Hou. J. Am. Chem. Soc. 134, 14314 (2012);
47. R. Alfaro A. Parra J. Alemán J. L. G. Ruano M. Tortosa. J. Am. Chem. Soc. 134 15165 2012)
48. Y. Takemoto, H. Yoshida, K. Takaki. Chem.-Eur. J. 18, 14841 (2012);
49. K. Kubota, E. Yamamoto, H. Ito. J. Am. Chem. Soc. 135, 2635 (2013);
50. P. Liu, Y. Fukui, P. Tian, Z.-T. He, C.-Y. Sun, N.-Y. Wu, G.-Q. Lin. J. Am. Chem. Soc. 135, 11700 (2013).
51. D. S. Laitar, E. Y. Tsui, J. P. Sadighi. Organometallics 25, 2405 (2006).
52. For reviews, see: (a) T. E. Müller, K. C. Hultzsch, M. Yus, F. Foubelo, M. Tada. Chem. Rev. 108, 3795 (2008);
53. Y. Fukumoto. J. Synth. Org. Chem. Jpn. 67 735 2009)
54. K. D. Hesp, M. Stradiotto. ChemCatChem 2, 1192 (2010);
55. J. F. Hartwig. Organotransition Metal Chemistry: From Bonding to Catalysis, Vol. 1, p. 700, University Science Books, Sausalito, CA (2010).
56. M. Kawatsura, J. F. Hartwig. J. Am. Chem. Soc. 122, 9546 (2000);
57. U. Nettekoven, J. F. Hartwig. J. Am. Chem. Soc. 124, 1166 (2002);
58. M. Utsunomiya, R. Kuwano, M. Kawatsura, J. F. Hartwig. J. Am. Chem. Soc. 125, 5608 (2003);
59. M. Ustunomiya, J. F. Hartwig. J. Am. Chem. Soc. 125, 14286 (2003);
60. J.-S. Ryu, G. Y. Li, T. J. Marks. J. Am. Chem. Soc. 125, 12584 (2003);
61. M. Utsunomiya, J. F. Hartwig. J. Am. Chem. Soc. 126, 2702 (2004);
62. J. Takaya, J. F. Hartwig. J. Am. Chem. Soc. 127, 5756 (2005);
63. H. Qian, R. A. Widenhoefer. Org. Lett. 7, 2635 (2005);
64. S. G. Pan, K. Endo, T. Shibata. Org. Lett. 14, 780 (2012).
65. For leading work on the generation of Cu-H species with PMHS, see: (a) B. H. Lipshutz, K. Noson, W. Chrisman. J. Am. Chem. Soc. 123, 12917 (2001);
66. B. H. Lipshutz A. Lower K. Nolan. Org. Lett. 4 4045 2002
67. B. H. Lipshutz, J. M. Servesko, B. R. Taft. J. Am. Chem. Soc. 126, 8352 (2004);
68. B. H. Lipshutz, J. M. Servesko, T. B. Peterson, P. P. Papa, A. A. Lover. Org. Lett. 6, 1273 (2004);
69. B. A. Baker, Z. V. Boskovic, B. H. Lipshutz. Org. Lett. 10, 289 (2008).