Copper-catalyzed intermolecular carboetherification of unactivated alkenes by Alkyl nitriles and alcohols

Angewandte Chemie - International Edition

Volumn 54, Issue 18, 2015, Pages 5443-5446

  Chatalova Sazepin, Claire ^a   Wang, Qian ^b   Sammis, Glenn M ^a   Zhu, Jieping ^b  

^a UNIVERSITY OF BRITISH COLUMBIA   (Canada)

^b EPFL   (Switzerland)

Author keywords

alkenes; carboetherification; copper catalysts; difunctionalization; oxyalkylation

Indexed keywords

CATALYSTS; COPPER; HYDROCARBONS; OLEFINS; REACTION INTERMEDIATES; STYRENE;

ALKYL RADICALS; CARBOETHERIFICATION; COPPER CATALYST; COPPER CATALYZED; DIFUNCTIONALIZATION; OXYALKYLATION; QUATERNARY CARBON; THREE COMPONENT;

CYANIDES;

EID: 84928034375     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201412357     Document Type: Article

References (87)

1. S. R. Chemler, P. H. Fuller, Chem. Soc. Rev. 2007, 36, 1153-1160
2. A. Minatti, K. Muniz, Chem. Soc. Rev. 2007, 36, 1142-1152
3. K. H. Jensen, M. S. Sigman, Org. Biomol. Chem. 2008, 6, 4083-4088
4. R. I. McDonald, G. Liu, S. S. Stahl, Chem. Rev. 2011, 111, 2981-3019
5. C. Zhang, C. Tang, N. Jiao, Chem. Soc. Rev. 2012, 41, 3464-3484
6. Y. Shimizu, M. Kanai, Tetrahedron Lett. 2014, 55, 3727-3737
7. D. M. Schultz, J. P. Wolfe, Synthesis 2012, 351-361.
8. J. P. Wolfe, Eur. J. Org. Chem. 2007, 571-582.
9. Cu-catalyzed intramolecular carboetherification has been developed by Chemler, see
10. Y. Miller, L. Miao, A. S. Hosseini, S. R. Chemler, J. Am. Chem. Soc. 2012, 134, 12149-12156
11. M. T. Bovino, T. W. Liwosz, N. E. Kendel, Y. Miller, N. Tyminska, E. Zurek, S. R. Chemler, Angew. Chem. Int. Ed. 2014, 53, 6383-6387
12. Angew. Chem. 2014, 126, 6501-6505.
13. Oxytrifluoromethylations
14. H. Egami, R. Shimizu, M. Sodeoka, Tetrahedron Lett. 2012, 53, 5503-5506
15. Y. Yasu, T. Koike, M. Akita, Angew. Chem. Int. Ed. 2012, 51, 9567-9571
16. Angew. Chem. 2012, 124, 9705-9709
17. Y. Li, A. Studer, Angew. Chem. Int. Ed. 2012, 51, 8221-8224
18. Angew. Chem. 2012, 124, 8345-8348
19. P. G. Janson, I Ghoneim, N. O. Ilchenko, K. J. Szabõ, Org. Lett. 2012, 14, 2882-2885.
20. Oxyarylation of alkenes
21. M. R. Heinrich, A. Wetzel, M. Kirschstein, Org. Lett. 2007, 9, 3833-3835
22. S. Kirchberg, R. Fröhlich, A. Studer, Angew. Chem. Int. Ed. 2010, 49, 6877-6880
23. Angew. Chem. 2010, 122, 7029-7032
24. A. D. Melhado, W. E. Brenzovich, Jr.; A. D. Lackner, F. D. Toste, J. Am. Chem. Soc. 2010, 132, 8885-8887
25. M. Hartmann, Y. Li, A. Studer, J. Am. Chem. Soc. 2012, 134, 16516-16519
26. G. Fumagalli, S. Boyd, M. F. Greaney, Org. Lett. 2013, 15, 4398-4401
27. M. N. Hopkinson, B. Sahoo, F. Glorius, Adv. Synth. Catal. 2014, 356, 2794-2800
28. W. Guo, H.-G. Cheng, L.-Y. Chen, J. Xuan, Z.-J. Feng, J.-R. Chen, L.-Q. Lu, W.-J. Xiao, Adv. Synth. Catal. 2014, 356, 2787-2793; Oxyarylation of allenes, see
29. T. Itoh, Y. Shimizu, M. Kanai, Org. Lett. 2014, 16, 2736-2739; For a review, see
30. M. R. Heinrich, Chem. Eur. J. 2009, 15, 820-833.
31. P. Eisenberger, S. Gischig, A. Togni, Chem. Eur. J. 2006, 12, 2579-2586.
32. T. H. Graham, C. M. Jones, N. T. Jui, D. W. C. MacMillan, J. Am. Chem. Soc. 2008, 130, 16494-16495.
33. H. Yi, X. Zhang, C. Qin, Z. Liao, J. Liu, A. Lei, Adv. Synth. Catal. 2014, 356, 2873-2877
34. Z. Liao, H. Yi, Z. Li, C. Fan, X. Zhang, J. Liu, Z. Deng, A. Lei, Chem. Asian J. 2015, 10, 96-99.
35. Z. Rappoport, The Chemistry of the Cyano Group, Wiley, London, 1970.
36. For the formation of organometallic complexes of acetonitrile using a stoichiometric amount of metals, see
37. S. D. Ittel, C. A. Tolman, A. D. English, J. P. Jesson, J. Am. Chem. Soc. 1978, 100, 7577-7585
38. H. J. Heeres, A. Meetsma, J. H. Teuben, Angew. Chem. Int. Ed. Engl. 1990, 29, 420-422
39. Angew. Chem. 1990, 102, 449-450
40. D. Churchill, J. H. Shin, T. Hascall, J. M. Hahn, B. M. Bridgewater, G. Parkin, Organometallics 1999, 18, 2403-2406
41. M. E. Evans, T. Li, A. J. Vetter, R. D. Rieth, W. D. Jones, J. Org. Chem. 2009, 74, 6907-6914.
42. Addition to aldehydes, Cu-catalyzed
43. Y. Suto, N. Kumagai, S. Matsunaga, M. Kanai, M. Shibasaki, Org. Lett. 2003, 5, 3147-3150
44. Y. Suto, R. Tsuji, M. Kanai, M. Shibasaki, Org. Lett. 2005, 7, 3757-3760
45. G.-W. Wang, A.-X. Zhou, J.-J. Wang, R.-B. Hu, S.-D. Yang, Org. Lett. 2013, 15, 5270-5273
46. J. Shen, D. Yang, Y. Liu, S. Qin, J. Zhang, J. Sun, C. Liu, C. Liu, X. Zhao, C. Chu, R. Liu, Org. Lett. 2014, 16, 350-353. Ru-catalyzed
47. N. Kumagai, S. Matsunaga, M. Shibasaki, J. Am. Chem. Soc. 2004, 126, 13632-13633
48. N. Kumagai, S. Matsunaga, M. Shibasaki, Tetrahedron 2007, 63, 8598-8608; Ni-catalyzed
49. S. Chakraborty, Y. J. Patel, J. A. Krause, H. Guan, Angew. Chem. Int. Ed. 2013, 52, 7523-7526
50. Angew. Chem. 2013, 125, 7671-7674.
51. Difunctionalization of activated alkenes with acetonitrile, Pd-catalyzed
52. T. Wu, X. Mu, G. Liu, Angew. Chem. Int. Ed. 2011, 50, 12578-12581
53. Angew. Chem. 2011, 123, 12786-12789; Cu-catalyzed
54. J. Li, Z. Wang, N. Wu, G. Gao, J. You, Chem. Commun. 2014, 50, 15049-15051
55. D. Zhou, Z.-H. Li, J. Li, S.-H. Li, M.-W. Wang, X.-L. Luo, G.-L. Ding, R.-L. Sheng, M.-J. Fu, S. Tang, Eur. J. Org. Chem. 2015, 7, 1606-1612; Fe-catalyzed
56. C. Pan, H. Zhang, C. Zhu, Org. Biomol. Chem. 2015, 13, 361.
57. Difunctionalization of alkynes
58. B. Yao, Q. Wang, J. Zhu, Angew. Chem. Int. Ed. 2012, 51, 5170-5174
59. Angew. Chem. 2012, 124, 5260-5264
60. B. Yao, Q. Wang, J. Zhu, Angew. Chem. Int. Ed. 2012, 51, 12311-12315
61. Angew. Chem. 2012, 124, 12477-12481
62. B. Yao, Q. Wang, J. Zhu, Angew. Chem. Int. Ed. 2013, 52, 12992-12996
63. Angew. Chem. 2013, 125, 13230-13234.
64. A. Bunescu, Q. Wang, J. Zhu, Chem. Eur. J. 2014, 20, 14633-14636
65. A. Bunescu, Q. Wang, J. Zhu, Angew. Chem. Int. Ed. 2015, 54, 3132-3135
66. Angew. Chem. Int. Ed. 2015, 125, 3175-3178.
67. Giese et al. have developed an elegant three-step synthesis of this family of compounds from ketones and acrylonitrile, see
68. B. Giese, U. Erfort, Angew. Chem. Int. Ed. Engl. 1982, 21, 130-131
69. Angew. Chem. 1982, 94, 133.
70. 1,1-Diarylethylenes undergo copper-catalyzed oxidation to benzophenone in the presence of oxygen and peroxide:, M. M. Hossain, S.-G. Shyu, Tetrahedron 2014, 70, 251-255.
71. T. W. Liwosz, S. R. Chemler, Chem. Eur. J. 2013, 19, 12771-12777.
72. J. F. Normant, A. Alexakis, Synthesis 1981, 841-870
73. E. Nakamura, M. Isaka, S. Mstsuzawa, J. Am. Chem. Soc. 1988, 110, 1297-1298
74. L. Huang, H. Jiang, C. Qi, X. Liu, J. Am. Chem. Soc. 2010, 132, 17652-17654
75. K. K. Toh, Y.-F. Wang, E. P. J. Ng, S. Chiba, J. Am. Chem. Soc. 2011, 133, 13942-13945.
76. T. W. Liwosz, S. R. Chemler, Org. Lett. 2013, 15, 3034-3037.
77. Copper(II)-catalyzed oxidation of benzylic radicals to benzylic cation, see
78. C. L. Jenkins, J. K. Kochi, J. Am. Chem. Soc. 1972, 94, 843-855
79. R. Zhu, S. L. Buchwald, J. Am. Chem. Soc. 2012, 134, 12462-12465
80. B. Zhang, A. Studer, Org. Lett. 2014, 16, 1790-1793.
81. G. E. Morris, D. Oakley, D. A. Pippard, D. J. H. Smith, J. Chem. Soc. Chem. Commun. 1987, 411-412
82. R. T. Gephart III, C. L. McMullin, N. G. Sapiezynski, E. S. Jang, M. J. B. Aguila, T. R. Cundari, T. H. Warren, J. Am. Chem. Soc. 2012, 134, 17350-17353.
83. For recent examples of Cu-peroxide mediated functionalization of activated alkenes by (cyclo)alkanes, see
84. M.-B. Zhou, R.-J. Song, X.-H. Ouyang, Y. Liu, W.-T. Wei, G.-B. Deng, J.-H. Li, Chem. Sci. 2013, 4, 2690-2694
85. S.-L. Zhou, L.-N. Guo, H. Wang, X.-H. Duan, Chem. Eur. J. 2013, 19, 12970-12973
86. Z. Li, Y. Zhang, L. Zhang, Z.-Q. Liu, Org. Lett. 2014, 16, 382-385.
87. For a review on radical-polar crossover multicomponent reaction, see:, E. Godineau, Y. Landais, Chem. Eur. J. 2009, 15, 3044-3055.