Chemoselective silylative reduction of conjugated nitriles under metal-free catalytic conditions: β-silyl amines and enamines

Angewandte Chemie - International Edition

Volumn 54, Issue 23, 2015, Pages 6832-6836

  Gandhamsetty, Narasimhulu ^a,b   Park, Juhyeon ^a,b   Jeong, Jinseong ^a,b   Park, Sung Woo ^a,b   Park, Sehoon ^a,b   Chang, Sukbok ^a,b  

^a Institute for Basic Science   (South Korea)

^b Korea Advanced Institute of Science and Technology (KAIST)   (South Korea)

Author keywords

boron; conjugation; hydrosilylation; reduction; synthetic methods

Indexed keywords

BORON; CATALYSIS; CYANIDES; HYDROSILYLATION; REDUCTION; SILANES;

CATALYTIC CONDITIONS; CHEMOSELECTIVE; CONJUGATION; ENAMINE INTERMEDIATES; ENAMINES; METAL FREE; MILD REACTION CONDITIONS; SYNTHETIC METHODS;

AMINES;

EID: 85027955732     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201502366     Document Type: Article

References (74)

1. E. Colvin, Silicon in Organic Synthesis II, Butterworth, Oxford, 1981, p. 325
2. E. Langkopf, D. Schinzer, Chem. Rev. 1995, 95, 1375
3. I. Fleming, A. Barbero, D. Walter, Chem. Rev. 1997, 97, 2063
4. Y. Nagai, Org. Prep. Proced. Int. 1980, 12, 13
5. C. Cheng, J. F. Hartwig, Chem. Rev. 2015, DOI:.
6. J. Wang, C. Ma, Y. Wu, R. A. Lamb, L. H. Pinto, W. F. DeGrado, J. Am. Chem. Soc. 2011, 133, 13844
7. A. K. Franz, P. D. Dreyfuss, S. L. Schreiber, J. Am. Chem. Soc. 2007, 129, 1020
8. A. K. Franz, S. O. Wilson, J. Med. Chem. 2013, 56, 388
9. S. Gately, R. West, Drug Dev. Res. 2007, 68, 156.
10. A. M. Tondreau, C. C. H. Atienza, K. J. Weller, S. A. Nye, K. M. Lewis, J. G. P. Delis, P. J. Chirik, Science 2012, 335, 567
11. I. Ojima, The Chemistry of Organic Silicon Compounds (Eds.:, S. Patai, Z. Rappoport,), Wiley Interscience, New York, 1989, p. 1479.
12. B. Marciniec, J. Gulinski, W. Urbaniak, Z. W. Kornetka, Comprehensive Handbook on Hydrosilylation (Ed.:, B. Marciniec,), Pergamon, Oxford, 2002, p. 3
13. B. Marciniec, Coord. Chem. Rev. 2005, 249, 2374.
14. M. Rubin, T. Schwier, V. Gevorgyan, J. Org. Chem. 2002, 67, 1936
15. E. M. Simmons, J. F. Hartwig, Nature 2012, 483, 70
16. A. Simonneau, M. Oestreich, Angew. Chem. Int. Ed. 2013, 52, 11905
17. Angew. Chem. 2013, 125, 12121.
18. S. C. Bergmeier, Tetrahedron 2000, 56, 2561
19. O. K. Karjalainen, A. M. P. Koskinen, Org. Biomol. Chem. 2012, 10, 4311
20. D. J. Ager, I. Prakash, D. R. Schaad, Chem. Rev. 1996, 96, 835
21. E. J. Corey, C. J. Helal, Angew. Chem. Int. Ed. 1998, 37, 1986
22. Angew. Chem. 1998, 110, 2092.
23. C. Bornschein, S. Werkmeister, B. Wendt, H. Jiao, E. Alberico, W. Baumann, H. Junge, K. Junge, M. Beller, Nat. Commun. 2014, 5, 4111
24. M. Perez, Z.-W. Qu, C. B. Caputo, V. Podgorny, L. J. Hounjet, A. Hansen, R. Dobrovetsky, S. Grimme, D. W. Stephan, Chem. Eur. J. 2015, DOI:, and references therein.
25. K. Ishihara, H. Yamamoto, Eur. J. Org. Chem. 1999, 527
26. J. M. Blackwell, E. R. Sonmor, T. Scoccitti, W. E. Piers, Org. Lett. 2000, 2, 3921
27. V. Gevorgyan, J.-X. Liu, M. Rubin, S. Benson, Y. Yamamoto, Tetrahedron Lett. 1999, 40, 8919
28. M. Tan, Y. Zhang, Tetrahedron Lett. 2009, 50, 4912
29. J. M. Blackwell, D. J. Morrison, W. E. Piers, Tetrahedron 2002, 58, 8247
30. R. C. Chadwick, V. Kardelis, P. Lim, A. Adronov, J. Org. Chem. 2014, 79, 7728
31. M. Oestreich, J. Hermeke, J. Mohr, Chem. Soc. Rev. 2015, DOI:.
32. P. Spies, S. Schwendemann, S. Lange, G. Kehr, R. Fröhlich, G. Erker, Angew. Chem. Int. Ed. 2008, 47, 7543
33. Angew. Chem. 2008, 120, 7654
34. Y. Liu, H. Du, J. Am. Chem. Soc. 2013, 135, 12968
35. T. Mahdi, J. N. Castillo, D. W. Stephan, Organometallics 2013, 32, 1971
36. T. A. Rokob, A. Hamza, A. Stirling, I. Papai, J. Am. Chem. Soc. 2009, 131, 2029.
37. P. A. Chase, G. C. Welch, T. Jurca, D. W. Stephan, Angew. Chem. Int. Ed. 2007, 46, 8050
38. Angew. Chem. 2007, 119, 8196
39. P. A. Chase, T. Jurca, D. W. Stephan, Chem. Commun. 2008, 1701.
40. N. Komine, M. Abe, R. Suda, M. Hirano, Organometallics 2015, 34, 432
41. A. M. Caporusso, N. Panziera, P. Pertici, E. Pitzalis, P. Salvadori, G. Vitulli, G. Martra, J. Mol. Catal. A 1999, 150, 275
42. H. Dong, Y. Jiang, H. Berke, J. Organomet. Chem. 2014, 750, 17
43. I. Ojima, M. Kumagai, J. Organomet. Chem. 1976, 111, 43
44. R. K. Dieter, K. Lu, S. E. Velu, J. Org. Chem. 2000, 65, 8715
45. T. Murai, T. Sakane, S. Kato, J. Org. Chem. 1990, 55, 449.
46. N. Gandhamsetty, J. Seewon, P. Sung-Woo, P. Sehoon, S. Chang, J. Am. Chem. Soc. 2014, 136, 16780.
47. V. Gevorgyan, M. Rubin, S. Benson, J.-X. Liu, Y. Yamamoto, J. Org. Chem. 2000, 65, 6179
48. T. Robert, M. Oestreich, Angew. Chem. Int. Ed. 2013, 52, 5216
49. Angew. Chem. 2013, 125, 5324
50. M. Yasuda, Y. Onishi, M. Ueba, T. Miyai, A. Baba, J. Org. Chem. 2001, 66, 7741.
51. K. Tamao, N. Ishida, T. Tanaka, M. Kumada, Organometallics 1983, 2, 1694
52. R. Shchepin, C. Xu, P. Dussault, Org. Lett. 2010, 12, 4772.
53. H. Jacobsen, H. Berke, S. Doring, G. Kehr, G. Erker, R. Frohlich, O. Meyer, Organometallics 1999, 18, 1724.
54. H. Wang, R. Fröhlich, G. Kehr, G. Erker, Chem. Commun. 2008, 5966
55. D. J. Parks, W. E. Piers, J. Am. Chem. Soc. 1996, 118, 9440
56. A. Y. Houghton, J. Hurmalainen, A. Mansikkamäki, W. E. Piers, H. M. Tuononen, Nat. Chem. 2014, 6, 983
57. D. J. Parks, J. M. Blackwell, W. E. Piers, J. Org. Chem. 2000, 65, 3090
58. S. Rendler, M. Oestreich, Angew. Chem. Int. Ed. 2008, 47, 5997
59. Angew. Chem. 2008, 120, 6086.
60. L. J. Hounjet, D. W. Stephan, Org. Process Res. Dev. 2014, 18, 385
61. M. Mewald, M. Oestreich, Chem. Eur. J. 2012, 18, 14079
62. G. I. Nikonov, S. F. Vyboishchikov, O. G. Shirobokov, J. Am. Chem. Soc. 2012, 134, 5488
63. K. Sakata, H. Fujimoto, J. Org. Chem. 2013, 78, 12505
64. J. M. Blackwell, K. L. Foster, V. H. Beck, W. E. Piers, J. Org. Chem. 1999, 64, 4887.
65. D. V. Gutsulyak, A. Van Der Est, G. I. Nikonov, Angew. Chem. Int. Ed. 2011, 50, 1384
66. Angew. Chem. 2011, 123, 1420
67. D. V. Gutsulyak, G. I. Nikonov, Angew. Chem. Int. Ed. 2010, 49, 7553
68. Angew. Chem. 2010, 122, 7715.
69. S. E. Denmark, T. W. Wilson, Angew. Chem. Int. Ed. 2012, 51, 9980
70. Angew. Chem. 2012, 124, 10120.
71. R. J. P. Corriu, J. J. E. Moreau, M. Pataud-Sat, J. Org. Chem. 1990, 55, 2878
72. J. Hermeke, H. F. T. Klare, M. Oestreich, Chem. Eur. J. 2014, 20, 9250
73. J. Hermeke, M. Mewald, M. Oestreich, J. Am. Chem. Soc. 2013, 135, 17537
74. S. J. Geier, P. A. Chase, D. W. Stephan, Chem. Commun. 2010, 46, 4884.