Highly Stereoselective Cobalt(III)-Catalyzed Three-Component C−H Bond Addition Cascade

Angewandte Chemie - International Edition

Volumn 55, Issue 41, 2016, Pages 12650-12654

  Boerth, Jeffrey A ^a   Hummel, Joshua R ^a   Ellman, Jonathan A ^a  

^a YALE UNIVERSITY   (United States)

Author keywords

C H activation; diastereoselectivity; homogeneous catalysis; multicomponent reactions

Indexed keywords

ALDEHYDES; AMINES; AROMATIC COMPOUNDS; CATALYSIS; COBALT COMPOUNDS; STEREOSELECTIVITY; TRANSITION METALS;

ADDITION PRODUCTS; ASYMMETRIC REACTION; ASYMMETRIC SYNTHESIS; DIASTEREO-SELECTIVITY; EFFICIENT COUPLING; FUNCTIONALIZATIONS; HOMOGENEOUS CATALYSIS; MULTI-COMPONENT REACTIONS;

ADDITION REACTIONS;

ALDEHYDE; AMINE; COBALT; IMINE; PYRAZOLE; PYRAZOLE DERIVATIVE; PYRIDINE; PYRIDINE DERIVATIVE;

CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; STEREOISOMERISM; SYNTHESIS;

ALDEHYDES; AMINES; CATALYSIS; COBALT; IMINES; MOLECULAR STRUCTURE; PYRAZOLES; PYRIDINES; STEREOISOMERISM;

EID: 84992183832     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201603831     Document Type: Article

References (86)

1. For recent reviews on C−H functionalization, see:
2. T. Gensch, M. N. Hopkinson, F. Glorius, J. Wencel-Delord, Chem. Soc. Rev. 2016, Advance Article, DOI: 10.1039/C6CS00075D;
3. L. Yang, H. Huang, Chem. Rev. 2015, 115, 3468;
4. J. Wencel-Delord, F. Glorius, Nat. Chem. 2013, 5, 369;
5. P. B. Arockiam, C. Bruneau, P. H. Dixneuf, Chem. Rev. 2012, 112, 5879;
6. B.-J. Li, Z.-J. Shi, Chem. Soc. Rev. 2012, 41, 5588;
7. J. Yamaguchi, A. D. Yamaguchi, K. Itami, Angew. Chem. Int. Ed. 2012, 51, 8960;
8. Angew. Chem. 2012, 124, 9092;
9. K. M. Engle, T.-S. Mei, M. Wasa, J.-Q. Yu, Acc. Chem. Res. 2012, 45, 788;
10. D. A. Colby, A. S. Tsai, R. G. Bergman, J. A. Ellman, Acc. Chem. Res. 2012, 45, 814;
11. L. Ackermann, Chem. Rev. 2011, 111, 1315;
12. S. H. Cho, J. Y. Kim, J. Kwak, S. Chang, Chem. Soc. Rev. 2011, 40, 5068.
13. For reviews on C−H bond additions to polarized π-bonds, see:
14. X.-Y. Shi, W.-J. Han, C.-J. Li, Chem. Rec. 2016, Early View, DOI: 10.1002/tcr.201500250;
15. X.-S. Zhang, K. Chen, Z.-J. Shi, Chem. Sci. 2014, 5, 2146;
16. G. Yan, X. Wu, M. Yang, Org. Biomol. Chem. 2013, 11, 5558.
17. III-catalyzed C−H bond functionalization, see:
18. G. Song, F. Wang, X. Li, Chem. Soc. Rev. 2012, 41, 3651;
19. F. W. Patureau, J. Wencel-Delord, F. Glorius, Aldrichimica Acta 2012, 45, 31;
20. T. Satoh, M. Miura, Chem. Eur. J. 2010, 16, 11212.
21. III-catalyzed C−H bond functionalization, see:
22. M. Moselage, J. Li, L. Ackermann, ACS Catal. 2016, 6, 498;
23. D. Wei, X. Zhu, J.-L. Niu, M.-P. Song, ChemCatChem 2016, 8, 1242;
24. N. Yoshikai, ChemCatChem 2015, 7, 732.
25. III-catalyzed C−H bond additions to π-bonds, see:
26. A. Lerchen, S. Vasquez-Cespedes, F. Glorius, Angew. Chem. Int. Ed. 2016, 55, 3208;
27. Angew. Chem. 2016, 128, 3261;
28. S.-S. Zhang, X.-G. Liu, S.-Y. Chen, D.-H. Tan, C.-Y. Jiang, J.-Q. Wu, Q. Li, H. Wang, Adv. Synth. Catal. 2016, Early View, DOI: 10.1002/adsc.201600025;
29. H. Wang, M. Moselage, M. J. Gonzalez, L. Ackermann, ACS Catal. 2016, 6, 2705;
30. Z.-Z. Zhang, B. Liu, J.-W. Xu, S.-Y. Yan, B.-F. Shi, Org. Lett. 2016, 18, 1776;
31. M. Sen, B. Emayavaramban, N. Barsu, J. R. Premkumar, B. Sundararaju, ACS Catal. 2016, 6, 2792;
32. G. Sivakumar, A. Vijeta, M. Jeganmohan, Chem. Eur. J. 2016, 22, 5899;
33. F. Wang, H. Wang, Q. Wang, S. Yu, X. Li, Org. Lett. 2016, ASAP, DOI: 10.1021/acs.orglett.6b00227;
34. L. Kong, S. Yu, X. Zhou, X. Li, Org. Lett. 2016, 18, 588;
35. T. T. Nguyen, L. Grigorjeva, O. Daugulis, ACS Catal. 2016, 6, 551;
36. S. Prakash, K. Muralirajan, C.-H. Cheng, Angew. Chem. Int. Ed. 2016, 55, 1844;
37. Angew. Chem. 2016, 128, 1876;
38. N. Barsu, M. Sen, J. R. Premkumar, B. Sundararaju, Chem. Commun. 2016, 52, 1338;
39. K. Muralirajan, R. Kuppusamy, S. Prakash, C.-H. Cheng, Adv. Synth. Catal. 2016, 358, 774;
40. Y. Liang, N. Jiao, Angew. Chem. Int. Ed. 2016, 55, 4035;
41. Angew. Chem. 2016, 128, 4103;
42. X.-G. Liu, S.-S. Zhang, C.-Y. Jiang, J.-Q. Wu, Q. Li, H. Wang, Org. Lett. 2015, 17, 5404;
43. J. R. Hummel, J. A. Ellman, Org. Lett. 2015, 17, 2400;
44. M. Sen, D. Kalsi, B. Sundararaju, Chem. Eur. J. 2015, 21, 15529;
45. T. Gensch, S. Vasquez-Cespedes, D.-G. Yu, F. Glorius, Org. Lett. 2015, 17, 3714;
46. J. Li, L. Ackermann, Angew. Chem. Int. Ed. 2015, 54, 8551;
47. Angew. Chem. 2015, 127, 8671;
48. H. Wang, J. Koeller, W. Liu, L. Ackermann, Chem. Eur. J. 2015, 21, 15525;
49. W. Ma, L. Ackermann, ACS Catal. 2015, 5, 2822;
50. Y. Suzuki, B. Sun, T. Yoshino, M. Kanai, S. Matsunaga, Tetrahedron 2015, 71, 4552;
51. J. R. Hummel, J. A. Ellman, J. Am. Chem. Soc. 2015, 137, 490;
52. J. Li, L. Ackermann, Angew. Chem. Int. Ed. 2015, 54, 3635;
53. Angew. Chem. 2015, 127, 3706;
54. D.-G. Yu, T. Gensch, F. de Azambuja, S. Vasquez-Cespedes, F. Glorius, J. Am. Chem. Soc. 2014, 136, 17722;
55. L. Grigorjeva, O. Daugulis, Angew. Chem. Int. Ed. 2014, 53, 10209;
56. Angew. Chem. 2014, 126, 10373;
57. L. Grigorjeva, O. Daugulis, Org. Lett. 2014, 16, 4684;
58. L. Grigorjeva, O. Daugulis, Org. Lett. 2014, 16, 4688;
59. T. Yoshino, H. Ikemoto, S. Matsunaga, M. Kanai, Chem. Eur. J. 2013, 19, 9142;
60. T. Yoshino, H. Ikemoto, S. Matsunaga, M. Kanai, Angew. Chem. Int. Ed. 2013, 52, 2207;
61. Angew. Chem. 2013, 125, 2263.
62. Q. Lu, S. Vasquez-Cespedes, T. Gensch, F. Glorius, ACS Catal. 2016, 6, 2352;
63. J. Park, S. Chang, Angew. Chem. Int. Ed. 2015, 54, 14103;
64. Angew. Chem. 2015, 127, 14309;
65. B. Sun, T. Yoshino, M. Kanai, S. Matsunaga, Angew. Chem. Int. Ed. 2015, 54, 12968;
66. Angew. Chem. 2015, 127, 13160;
67. Y. Suzuki, B. Sun, K. Sakata, T. Yoshino, S. Matsunaga, M. Kanai, Angew. Chem. Int. Ed. 2015, 54, 9944;
68. Angew. Chem. 2015, 127, 10082;
69. D. Zhao, J. H. Kim, L. Stegemann, C. A. Strassert, F. Glorius, Angew. Chem. Int. Ed. 2015, 54, 4508;
70. Angew. Chem. 2015, 127, 4591;
71. H. Ikemoto, T. Yoshino, K. Sakata, S. Matsunaga, M. Kanai, J. Am. Chem. Soc. 2014, 136, 5424.
72. J. A. Boerth, J. A. Ellman, Chem. Sci. 2016, 7, 1474.
73. For a review on cascade Michael/aldol reactions, see: E. V. Gorobets, M. S. Miftakhov, F. A. Valeev, Russ. Chem. Rev. 2000, 69, 1001.
74. I-catalyzed examples, see:
75. D. F. Cauble, J. D. Gipson, M. J. Krische, J. Am. Chem. Soc. 2003, 125, 1110;
76. R. R. Huddleston, M. J. Krische, Org. Lett. 2003, 5, 1143; For CuII-catalyzed examples, see:
77. A. Alexakis, G. P. Trevitt, G. Bernardinelli, J. Am. Chem. Soc. 2001, 123, 4358;
78. L. A. Arnold, R. Naasz, A. J. Minnaard, B. L. Feringa, J. Am. Chem. Soc. 2001, 123, 5841;
79. B. L. Feringa, M. Pineschi, L. A. Arnold, R. Imbos, A. H. M. de Vries, Angew. Chem. Int. Ed. Engl. 1997, 36, 2620;
80. Angew. Chem. 1997, 109, 2733; For a CoII-catalyzed example, see:
81. T. G. Baik, A. L. Luis, J. C. Wang, M. J. Krische, J. Am. Chem. Soc. 2001, 123, 5112; For a Ni0-catalyzed example, see:
82. J. Montgomery, E. Oblinger, A. V. Savchenko, J. Am. Chem. Soc. 1997, 119, 4911.
83. Information. CCDCSynthetic details, characterization, and molecular structures obtained by X-ray structural analysis are described in the Supporting 1471274 (4 q) and 1471275 (12 a) contain the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre www.ccdc.cam.ac.uk/data_request/cif.
84. III-catalyzed three-component coupling reported in Ref. [7], a related active rhodium enolate has been characterized by X-Ray crystallography.
85. M. T. Robak, M. A. Herbage, J. A. Ellman, Chem. Rev. 2010, 110, 3600;
86. F. Ferreira, C. Botuha, F. Chemla, A. Pérez-Luna, Chem. Soc. Rev. 2009, 38, 1162.