Nickel catalyzed dealkoxylative Csp2-Csp3 cross coupling reactions - Stereospecific synthesis of allylsilanes from enol ethers

Chemical Communications

Volumn 51, Issue 10, 2015, Pages 1937-1940

  Guo, Lin ^a   Leiendecker, Matthias ^a   Hsiao, Chien Chi ^a   Baumann, Christoph ^a   Rueping, Magnus ^a  

^a RWTH AACHEN UNIVERSITY   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

ALLYL COMPOUND; ETHER DERIVATIVE; NICKEL; SILANE DERIVATIVE;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CROSS COUPLING REACTION; REACTION ANALYSIS; STEREOSPECIFICITY; SYNTHESIS;

EID: 84921690402     PISSN: 13597345     EISSN: 1364548X     Source Type: Journal    
DOI: 10.1039/c4cc08187k     Document Type: Article

References (79)

1. (a) D.-G. Yu, B.-J. Li and Z. - J. Shi, Acc. Chem. Res., 2010, 43, 1486;
2. (b) G. P. McGlacken and S. L. Clarke, ChemCatChem, 2011, 3, 1260;
3. (c) T. Mesganaw and N. K. Garg, Org. Process Res. Dev., 2013, 17, 29;
4. (d) S. I. Kozhushkov, H. K. Potukuchi and L. Ackermann, Catal. Sci. Technol., 2013, 3, 562;
5. (e) J. Cornella, C. Zarate and R. Martin, Chem. Soc. Rev., 2014, 43, 8081.
6. (a) J. W. Dankwardt, Angew. Chem., Int. Ed., 2004, 43, 2428;
7. (b) L.-G. Xie and Z.-X. Wang, Chem. - Eur. J., 2011, 17, 4972;
8. (c) M. J. Iglesias, A. Prieto and C. Nicasio, Org. Lett., 2012, 14, 4318;
9. (d) E. Wenkert, E. L. Michelotti and C. S. Swindell, J. Am. Chem. Soc., 1979, 108, 2246;
10. (e) M. Tobisu, T. Shimasaki and N. Chatani, Angew. Chem., Int. Ed., 2008, 47, 4866;
11. (f) C. Wang, T. Ozaki, R. Takita and M. Uchiyama, Chem. - Eur. J., 2012, 18, 3482.
12. B.-T. Guan, S.-K. Xiang, T. Wu, Z.-P. Sun, B.-Q. Wang, K.-Q. Zhao and Z.-J. Shi, Chem. Commun., 2008, 1437.
13. (a) P. Álvarez-Bercedo and R. Martin, J. Am. Chem. Soc., 2010, 132, 17352;
14. (b) A. G. Sergeev and J. F. Hartwig, Science, 2011, 332, 439;
15. (c) M. Tobisu, K. Yamakawa, T. Shimasaki and N. Chatani, Chem. Commun., 2011, 47, 2946;
16. (d) A. G. Sergeev, J. D. Webb and J. F. Hartwig, J. Am. Chem. Soc., 2012, 134, 20226;
17. (e) V. Molinari, C. Giordano, M. Antonietti and D. Esposito, J. Am. Chem. Soc., 2014, 136, 1758.
18. (a) C. M. Hill, R. Walker and M. Hill, J. Am. Chem. Soc., 1951, 73, 1663;
19. (b) E. Wenkert, E. L. Michelotti, C. S. Swindell and M. Tingoli, J. Org. Chem., 1984, 49, 4894;
20. (c) A. Liard and I. Marek, J. Org. Chem., 2000, 65, 7218;
21. (d) T. Shimasaki, Y. Konno, M. Tobisu and N. Chatani, Org. Lett., 2009, 11, 4890;
22. (e) L.-G. Xie and Z.-X. Wang, Chem. - Eur. J., 2011, 17, 4972
23. (f) E. Wenkert, M. H. Leftin and E. L. Michelotti, J. Chem. Soc., Chem. Commun., 1984, 617;
24. (g) S. Wadman, R. Whitby, C. Yeates, P. Kocienski and K. Cooper, J. Chem. Soc., Chem. Commun., 1987, 241;
25. (h) P. Kocienski, N. J. Dixon and S. Wadman, Tetrahedron Lett., 1988, 29, 2353;
26. (i) J. Cornella and R. Martin, Org. Lett., 2013, 15, 6298.
27. (a) F. Effenberger, Angew. Chem., Int. Ed., 1969, 8, 295;
28. (b) D. A. Evans and J. S. Johnson, J. Am. Chem. Soc., 1998, 120, 4895;
29. (c) W. Cabri, I. Candiani, A. Bedeschi and S. Penco, J. Org. Chem., 1992, 57, 1481;
30. (d) C. Nevado, D. J. Cárdenas and A. M. Echavarren, Chem. - Eur. J., 2003, 9, 2627.
31. (a) T. Hayashi, T. Fujiwa, Y. Okamoto, Y. Katsuro and M. Kumada, Synthesis, 1981, 1001;
32. (b) T. Hayashi, Y. Katsuro and M. Kumada, Tetrahedron Lett., 1980, 21, 3915.
33. (a) T. Hayashi, K. Kabeta, I. Hamachi and M. Kumada, Tetrahedron Lett., 1983, 24, 2865;
34. (b) D. R. Gauthier and E. M. Carreira, Angew. Chem., Int. Ed., 1996, 35, 2363;
35. (c) M. Suginome, T. Iwanami and Y. Ito, J. Am. Chem. Soc., 2001, 123, 4356;
36. (d) S. E. Denmark and J.-P. Fu, Chem. Rev., 2003, 103, 2763.
37. (a) S. Yamasaki, K. Fujii, R. Wada, M. Kanai and M. Shibasaki, J. Am. Chem. Soc., 2002, 124, 6536;
38. (b) H. Kiyohara, Y. Nakamura, R. Matsubara and S. Kobayashi, Angew. Chem., Int. Ed., 2006, 45, 1615;
39. (c) Q.-Y. Song, B.-L. Yang and S.-K. Tian, J. Org. Chem., 2007, 72, 5407.
40. (a) M. E. Jung and A. Maderna, J. Org. Chem., 2004, 69, 7755;
41. (b) H. M. Zerth, N. M. Leonard and R. S. Mohan, Org. Lett., 2003, 5, 55;
42. (c) D. Kampen and B. List, Synlett, 2006, 2589.
43. J. S. Yadav, B. V. S. Reddy, M. S. Reddy and G. Parimala, Synthesis, 2003, 2390.
44. (a) B. Greedy, J.-M. Paris, T. Vidal and V. Gouverneur, Angew. Chem., Int. Ed., 2003, 42, 3291;
45. (b) H. Teare, E. G. Robins, E. Arstad, S. K. Luthra and V. Gouverneur, Chem. Commun., 2007, 2330.
46. (a) R. Shimizu, H. Egami, Y. Hamashima and M. Sodeoka, Angew. Chem., Int. Ed., 2012, 51, 4577;
47. (b) S. Mizuta, O. Galicia-Lopez, K. M. Engle, S. Verhoog, K. Wheelhouse, G. Rassias and V. Gouverneur, Chem. - Eur. J., 2012, 18, 8583;
48. (c) J.-B. Liu, L.-L. Chu and F.-L. Qing, Org. Lett., 2013, 15, 894.
49. M. Arimoto, H. Yamaguchi and E. Fujita, Tetrahedron Lett., 1987, 28, 6289.
50. M. Ogasawara, Y. Ge, K. Uetake, L.-Y. Fan and T. Takahashi, J. Org. Chem., 2005, 70, 3871.
51. (a) J. Mazuela, J. J. Verendel, M. Coll, B. Schäffner, A. Börner, P. G. Andersson, O. Pàmies and M. Diéguez, J. Am. Chem. Soc., 2009, 131, 12344;
52. (b) J. Mazuela, P.-O. Norrby, P. G. Andersson, O. Pàmies and M. Diéguez, J. Am. Chem. Soc., 2011, 133, 13634;
53. (c) J. Mazuela, O. Pàmies and M. Diéguez, Adv. Synth. Catal., 2013, 355, 2569.
54. Y. Sawama, Y. Shishido, T. Yanase, K. Kawamoto, R. Goto, Y. Monguchi, Y. Kita and H. Sajiki, Angew. Chem., Int. Ed., 2013, 52, 1515.
55. S. Itsuno and T. Kumagai, Helv. Chim. Acta, 2002, 85, 3185.
56. (a) B.-L. Yang and S.-K. Tian, Chem. Commun., 2010, 46, 6180;
57. (b) T. Saito, Y. Nishimoto, M. Yasuda and A. Baba, J. Org. Chem., 2006, 71, 8516;
58. (c) M. Yasuda, T. Saito, M. Ueba and A. Baba, Angew. Chem., Int. Ed., 2004, 43, 1414;
59. (d) G. W. Kabalka, M.-L. Yao and S. Borella, J. Am. Chem. Soc. , 2006, 128, 11320;
60. (e) T. Sasaki, A. Usuki and M. Ohno, J. Org. Chem., 1980, 45, 3559.
61. S. A. Carr and W. P. Weber, J. Org. Chem., 1985, 50, 2782.
62. M. S. Dowling and C. D. Vanderwal, J. Org. Chem., 2010, 75, 6908.
63. (a) A. Hosomi, Acc. Chem. Res., 1988, 21, 200;
64. (b) T. K. Sarkar, Synthesis, 1990, 969-983;
65. (c) T. K. Sarkar, Synthesis, 1990, 1101.
66. M. Leiendecker, C.-C. Hsiao, L. Guo, N. Alandini and M. Rueping, Angew. Chem., Int. Ed., 2014, 53, 12912.
67. (a) C. Chen and P. S. Mariano, J. Org. Chem., 2000, 65, 3252;
68. (b) J. Kjellgren and K. J. Szabó, Tetrahedron Lett., 2002, 43, 1123;
69. (c) I. Macsári and K. J. Szabó, Chem. - Eur. J., 2001, 7, 4097;
70. (d) H. Hiemstra, M. A. M. Sno, R. J. Vijn and W. N. Speckamp, J. Org. Chem., 1985, 50, 4014;
71. (e) B. Grzeszczyk, B. Szechner, B. Furman and M. Chmielewski, Tetrahedron, 2010, 66, 3904;
72. (f) P. A. Grieco and W. F. Fobare, Tetrahedron Lett., 1986, 27, 5067.
73. (a) H. O. House, L. J. Czuba, M. Gall and H. D. Olmstead, J. Org. Chem., 1969, 34, 2324;
74. (b) P. Cazeau, F. Duboudin, F. Moulines, O. Babot and J. Dunogues, Tetrahedron, 1987, 43, 2075;
75. (c) P. Cazeau, F. Duboudin, F. Moulines, O. Babot and J. Dunogues, Tetrahedron, 1987, 43, 2089;
76. (d) J. J. Song, Z. Tan, J. T. Reeves, D. R. Fandrick, N. K. Yee and C. H. Senanayake, Org. Lett., 2008, 10, 877;
77. (e) C. D. F. Königs, H. F. T. Klare, Y. Ohki, K. Tatsumi and M. Oestreich, Org. Lett., 2012, 14, 2842.
78. (a) D. J. Peterson, J. Org. Chem., 1968, 33, 780;
79. (b) D. J. Ager, The Peterson Olefination Reaction in Organic Reactions, WILEY-VCH, Weinheim, 2004, pp. 1-223.