Copper-Catalyzed Asymmetric Borylation: Construction of a Stereogenic Carbon Center Bearing Both CF3 and Organoboron Functional Groups

Journal of Organic Chemistry

Volumn 82, Issue 4, 2017, Pages 1951-1960

  Jiang, Quanbin ^a   Guo, Tenglong ^a   Yu, Zhengkun ^a,b  

^a DALIAN INSTITUTE OF CHEMICAL PHYSICS   (China)

^b SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

CATALYSIS; KETONES; LIGANDS;

CHIRAL LIGAND; COPPER CATALYZED; EFFICIENT CATALYSTS; HIGH ENANTIOSELECTIVITY; KETONE DERIVATIVE; STEREOGENIC CARBONS; TRIFLUOROMETHYL; UNSATURATED KETONES;

COPPER;

CARBON; COPPER; FUNCTIONAL GROUP; KETONE DERIVATIVE; LIGAND; ORGANOBORON DERIVATIVE;

ARTICLE; ASYMMETRIC BORYLATION; CATALYSIS; CATALYST; CHEMICAL MODIFICATION; CHIRALITY; ENANTIOSELECTIVITY; REACTION OPTIMIZATION; SCREENING; STEREOSELECTIVITY;

EID: 85013149279     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/acs.joc.6b02772     Document Type: Article

References (67)

1. Organofluorine Chemistry, Uneyama, K., Ed.; Blackwell Publishing Ltd.: Oxford, 2006.
2. Fluorine-Containing Synthons; Soloshonok, V. A., Ed.; American Chemical Society: Washington, DC, 2005.
3. Yang, X.; Wu, T.; Phipps, R. J.; Toste, F. D. Chem. Rev. 2015, 115, 826 10.1021/cr500277b
4. Valero, G.; Companyó, X.; Rios, R. Chem.-Eur. J. 2011, 17, 2018 10.1002/chem.201001546
5. Ma, J.-A.; Cahard, D. Chem. Rev. 2008, 108, PR1 10.1021/cr800221v
6. Nie, J.; Guo, H.-C.; Cahard, D.; Ma, J.-A. Chem. Rev. 2011, 111, 455 10.1021/cr100166a
7. Mikami, K.; Itoh, Y.; Yamanaka, M. Chem. Rev. 2004, 104, 1 10.1021/cr030685w
8. Zhao, M.-X.; Zhu, H.-K.; Dai, T.-L.; Shi, M. J. Org. Chem. 2015, 80, 11330 10.1021/acs.joc.5b01829
9. Kwiatkowski, P.; Cholewiak, A.; Kasztelan, A. Org. Lett. 2014, 16, 5930 10.1021/ol502941d
10. Kawai, H.; Kitayama, T.; Tokunaga, E.; Matsumoto, T.; Sato, H.; Shiro, M.; Shibata, N. Chem. Commun. 2012, 48, 4067 10.1039/c2cc18049a
11. Davies, A. T.; Taylor, J. E.; Douglas, J.; Collett, C. J.; Morrill, L. C.; Fallan, C.; Slawin, A. M. Z.; Churchill, G.; Smith, A. D. J. Org. Chem. 2013, 78, 9243 10.1021/jo401433q
12. Wang, W.; Lian, X.; Chen, D.; Liu, X.; Lin, L.; Feng, X. Chem. Commun. 2011, 47, 7821 10.1039/c1cc12306h
13. Blay, G.; Fernández, I.; Muñoz, M. C.; Pedro, J. R.; Vila, C. Chem.-Eur. J. 2010, 16, 9117 10.1002/chem.201000568
14. Sanz-Marco, A.; García-Ortiz, A.; Blay, G.; Pedro, J. R. Chem. Commun. 2014, 50, 2275 10.1039/c3cc48508k
15. Morigaki, A.; Tanaka, T.; Miyabe, T.; Ishihara, T.; Konno, T. Org. Biomol. Chem. 2013, 11, 586 10.1039/C2OB26708J
16. Kawai, H.; Okusu, S.; Yuan, Z.; Tokunaga, E.; Yamano, A.; Shiro, M.; Shibata, N. Angew. Chem., Int. Ed. 2013, 52, 2221 10.1002/anie.201209355
17. Bizet, V.; Pannecoucke, X.; Renaud, J.-L.; Cahard, D. Angew. Chem., Int. Ed. 2012, 51, 6467 10.1002/anie.201200827
18. Kawai, H.; Okusu, S.; Tokunaga, E.; Sato, H.; Shiro, M.; Shibata, N. Angew. Chem., Int. Ed. 2012, 51, 4959 10.1002/anie.201201278
19. Synthesis and Applications of Organoboron Compounds, Topics in Organometallic Chemistry; Fernández, E.; Whiting, A., Eds.; Springer: Heidelberg, 2015.
20. Leonori, D.; Aggarwal, V. K. Angew. Chem., Int. Ed. 2015, 54, 1082 10.1002/anie.201407701
21. Leonori, D.; Aggarwal, V. K. Acc. Chem. Res. 2014, 47, 3174 10.1021/ar5002473
22. Scott, H. K.; Aggarwal, V. K. Chem.-Eur. J. 2011, 17, 13124 10.1002/chem.201102581
23. Crudden, C. M.; Glasspoole, B. W.; Lata, C. J. Chem. Commun. 2009, 6704 10.1039/b911537d
24. Neeve, E. C.; Geier, S. J.; Mkhalid, I. A. I.; Westcott, S. A.; Marder, T. B. Chem. Rev. 2016, 116, 9091 10.1021/acs.chemrev.6b00193
25. Stavber, G.; Časar, Z. ChemCatChem 2014, 6, 2162 10.1002/cctc.201402176
26. Calow, A. D. J.; Whiting, A. Org. Biomol. Chem. 2012, 10, 5485 10.1039/c2ob25908g
27. Hartmann, E.; Vyas, D. J.; Oestreich, M. Chem. Commun. 2011, 47, 7917 10.1039/c1cc10528k
28. Schiffner, J. A.; Müther, K.; Oestreich, M. Angew. Chem., Int. Ed. 2010, 49, 1194 10.1002/anie.200906521
29. Lee, J.-E.; Yun, J. Angew. Chem., Int. Ed. 2008, 47, 145 10.1002/anie.200703699
30. Kubota, K.; Hayama, K.; Iwamoto, H.; Ito, H. Angew. Chem., Int. Ed. 2015, 54, 8809 10.1002/anie.201502964
31. Niu, Z.; Chen, J.; Chen, Z.; Ma, M.; Song, C.; Ma, Y. J. Org. Chem. 2015, 80, 602 10.1021/jo5021135
32. He, Z.-T.; Zhao, Y.-S.; Tian, P.; Wang, C.-C.; Dong, H.-Q.; Lin, G.-Q. Org. Lett. 2014, 16, 1426 10.1021/ol500219e
33. Lee, J. C. H.; McDonald, R.; Hall, D. G. Nat. Chem. 2011, 3, 894 10.1038/nchem.1150
34. O'Brien, J. M.; Lee, K. -s.; Hoveyda, A. H. J. Am. Chem. Soc. 2010, 132, 10630 10.1021/ja104777u
35. Zhu, L.; Kitanosono, T.; Xu, P.; Kobayashi, S. Chem. Commun. 2015, 51, 11685 10.1039/C5CC04295J
36. Jiang, Q. B.; Guo, T. L.; Yu, Z. K. ChemCatChem 2015, 7, 660 10.1002/cctc.201402823
37. Xie, J.-B.; Lin, S.; Luo, J.; Wu, J.; Winn, T. R.; Li, G. Org. Chem. Front. 2015, 2, 42 10.1039/C4QO00271G
38. Kobayashi, S.; Xu, P.; Endo, T.; Ueno, M.; Kitanosono, T. Angew. Chem., Int. Ed. 2012, 51, 12763 10.1002/anie.201207343
39. Chen, I.-H.; Yin, L.; Itano, W.; Kanai, M.; Shibasaki, M. J. Am. Chem. Soc. 2009, 131, 11664 10.1021/ja9045839
40. Sim, H.-S.; Feng, X.; Yun, J. Chem.-Eur. J. 2009, 15, 1939 10.1002/chem.200802150
41. Molander, G. A.; Wisniewski, S. R.; Hosseini-Sarvari, M. Adv. Synth. Catal. 2013, 355, 3037 10.1002/adsc.201300640
42. Zhao, L.; Ma, Y.; Duan, W.; He, F.; Chen, J.; Song, C. Org. Lett. 2012, 14, 5780 10.1021/ol302839d
43. Sandrock, D. L.; Jean-Gérard, L.; Chen, C.-y.; Dreher, S. D.; Molander, G. A. J. Am. Chem. Soc. 2010, 132, 17108 10.1021/ja108949w
44. Moure, A. L.; Arrayás, R. G.; Carretero, J. C. Chem. Commun. 2011, 47, 6701 10.1039/c1cc11949d
45. Hornillos, V.; Vila, C.; Otten, E.; Feringa, B. L. Angew. Chem., Int. Ed. 2015, 54, 7867 10.1002/anie.201502987
46. Luo, Y.; Roy, I. D.; Madec, A. G. E.; Lam, H. W. Angew. Chem., Int. Ed. 2014, 53, 4186 10.1002/anie.201310380
47. Kitanosono, T.; Xu, P.; Kobayashi, S. Chem. Commun. 2013, 49, 8184 10.1039/c3cc44324h
48. Jarava-Barrera, C.; Parra, A.; López, A.; Cruz-Acosta, F.; Collado-Sanz, D.; Cárdenas, D. J.; Tortosa, M. ACS Catal. 2016, 6, 442 10.1021/acscatal.5b02742
49. Lou, Y.; Cao, P.; Jia, T.; Zhang, Y.; Wang, M.; Liao, J. Angew. Chem., Int. Ed. 2015, 54, 12134 10.1002/anie.201505926
50. Shiomi, T.; Adachi, T.; Toribatake, K.; Zhou, L.; Nishiyama, H. Chem. Commun. 2009, 45, 5987 10.1039/b915759j
51. Lillo, V.; Geier, M. J.; Westcott, S. A.; Fernández, E. Org. Biomol. Chem. 2009, 7, 4674 10.1039/b909341a
52. Radomkit, S.; Hoveyda, A. H. Angew. Chem., Int. Ed. 2014, 53, 3387 10.1002/anie.201309982
53. Wu, H.; Radomkit, S.; O'Brien, J. M.; Hoveyda, A. H. J. Am. Chem. Soc. 2012, 134, 8277 10.1021/ja302929d
54. Bonet, A.; Gulyás, H.; Fernández, E. Angew. Chem., Int. Ed. 2010, 49, 5130 10.1002/anie.201001198
55. Argintaru, O. A.; Ryu, D.; Aron, I.; Molander, G. A. Angew. Chem., Int. Ed. 2013, 52, 13656 10.1002/anie.201308036
56. Wang, Q.-D.; Yang, J.-M.; Fang, D.; Ren, J.; Dong, B.; Zhou, B.; Zeng, B.-B. Tetrahedron Lett. 2016, 57, 2587 10.1016/j.tetlet.2016.04.094
57. Uneyama, K.; Katagiri, T.; Amii, H. Acc. Chem. Res. 2008, 41, 817 10.1021/ar7002573
58. Ichikawa, J. J. Fluorine Chem. 2000, 105, 257 10.1016/S0022-1139(99)00268-7
59. Ichikawa, J.; Ikeura, C.; Minami, T. Synlett 1992, 1992, 739 10.1055/s-1992-21475
60. Funabiki, K.; Itoh, Y.; Kubota, Y.; Matsui, M. J. Org. Chem. 2011, 76, 3545 10.1021/jo200020z
61. Hupe, E.; Marek, I.; Knochel, P. Org. Lett. 2002, 4, 2861 10.1021/ol0262486
62. Ryu, D.; Primer, D. N.; Tellis, J. C.; Molander, G. A. Chem.-Eur. J. 2016, 22, 120 10.1002/chem.201504079
63. Jiang, Q. B.; Guo, T. L.; Wu, K. K.; Yu, Z. K. Chem. Commun. 2016, 52, 2913 10.1039/C5CC10361D
64. Yamazaki, T.; Kawasaki-Takasuka, T.; Furuta, A.; Sakamoto, S. Tetrahedron 2009, 65, 5945 10.1016/j.tet.2009.05.087
65. Aoyagi, K.; Haga, T.; Toi, H.; Aoyama, Y.; Mizutani, T.; Ogoshi, H. Bull. Chem. Soc. Jpn. 1997, 70, 937 10.1246/bcsj.70.937
66. Watanabe, Y.; Yamazaki, T. J. Org. Chem. 2011, 76, 1957 10.1021/jo102503s
67. Matoba, K.; Kawai, H.; Furukawa, T.; Kusuda, A.; Tokunaga, E.; Nakamura, S.; Shiro, M.; Shibata, N. Angew. Chem., Int. Ed. 2010, 49, 5762 10.1002/anie.201002065