Recent progress in the research of transition-metal-catalyzed C-CN bond cleavage

Chinese Journal of Organic Chemistry

Volumn 33, Issue 7, 2013, Pages 1407-1422

  Kou, Xuezhen ^a   Fan, Jiajun ^b   Tong, Xiaofeng ^a   Shen, Zengming ^b  

^a EAST CHINA UNIVERSITY OF SCIENCE AND TECHNOLOGY   (China)

^b SHANGHAI JIAO TONG UNIVERSITY   (China)

Author keywords

C CN bond cleavage; Mechanism; Transition metal

Indexed keywords

EID: 84882960623     PISSN: 02532786     EISSN: None     Source Type: Journal    
DOI: 10.6023/cjoc201212033     Document Type: Review

References (77)

1. Fatiadi A. J. In Preparation and Synthetic Applications of Cyano Compounds, Eds.: Patai S, Rappaport Z. Wiley New York 1983.
2. Kleemann A, Engel J, Kutscher B, Reichert D. Pharmaceutical Substances: Synthesis, Patents, Applications, 4th ed. Thieme Stuttgart, Germany, 2001.
3. Miller J. S, Manson J. L. Acc. Chem. Res. 2001 34 563.
4. Smith M. B, March J. March's Advanced Organic Chemistry: Reactions Mechanisms and Structure, 6th ed. Wiley Hoboken NJ 2007.
5. Rappoport Z. Chemistry of the Cyano Group Wiley, London, 1970.
6. Larock R. C. Comprehensive Organic Transformations, VCH Weinheim 1989 p. 819.
7. Anbarasan P, Schareina T, Beller M. Chem. Soc. Rev. 2011 40 5049.
8. For selected examples of transition-metal-catalyzed cyanantion of aryl halides see: (a) Takagi K, Okamoto T, Sakakibara Y, Oka S. Chem. Lett. 1973 471.
9. Zanon J, Klapars A, Buchwald S. L. J. Am. Chem. Soc. 2003 125 2890.
10. Sundermeier M, Zapf A, Beller M. Eur. J. Inorg. Chem. 2003 3513.
11. Zhou W, Xu J, Zhang L, Jiao N. Org. Lett. 2010 12 2888.
12. For selected examples of direct cyanation through C-H bond cleavage see: So Y.-H, Miller L. L. J. Am. Chem. Soc. 1980 102 7119.
13. Dohi T, Morimoto K, Kiyono Y, Tohma H, Kita Y. Org. Lett. 2005 7 537.
14. Zhou W, Zhang L, Jiao N. Angew. Chem. Int. Ed. 2009 48 7094.
15. Do H.-Q, Daugulis O. Org. Lett. 2010 12 2517.
16. Qin C, Jiao N. J. Am. Chem. Soc. 2010 132 15893.
17. Lu Z, Hu C, Guo J, Li J, Cui Y, Jia Y. Org. Lett. 2010 12 480.
18. For recent reviews see: (a) Yan G, Yu J, Zhang L. Chin. J. Org. Chem. 2012 32 294.
19. Kim J, Kim H, Chang S. Angew. Chem. Int. Ed. 2012 51 2.
20. Kim J, Chang S. J. Am. Chem. Soc. 2010 132 10272.
21. Ding S, Jiao N. J. Am. Chem. Soc. 2011 133 12374.
22. Ren X, Chen J, Chen F, Cheng J. Chem. Commun. 2011 47 6725.
23. Zhang G, Ren X, Chen J, Hu M, Cheng J. Org. Lett. 2011 13 5004.
24. Chen X, Hao X.-S, Goodhue C. E, Yu J.-Q. J. Am. Chem. Soc. 2006 128 6790.
25. Murahashi S. I, Naota T, Nakajima N. J. Org. Chem. 1986 51 898.
26. Nozaki K, Sato N, Takaya H. J. Org. Chem. 1994 59 2679.
27. Nishihara Y, Inoue Y, Izawa S, Miyasaka M, Tanemura K, Nakajima K, Takagi K. Tetrahedron 2006 62 9872.
28. Kobayashi Y, Kamisaki H, Yanada R, Takemoto Y. Org. Lett. 2006 8 2711.
29. Yasui Y, Kamisaki H, Takemoto Y. Org. Lett. 2008 10 3303.
30. Miller J. A. Tetrahedron Lett. 2001 42 6991.
31. Miller J. A, Dankwardt J. W. Tetrahedron Lett. 2003 44 1907.
32. Nakao Y, Oda S, Hiyama T. J. Am. Chem. Soc 2004 17 13904.
33. Nakao Y, Oda S, Yada A, Hiyama T. Tetrahedron 2006 62 7567.
34. Nakao Y, Yada A, Satoh J, Ebat S, Oda S, Hiyama T. Chem. Lett. 2006 35 790.
35. Nakao Y, Hirata Y, Hiyama T. J. Am. Chem. Soc. 2006 128 7420.
36. Hirata Y, Inui T, Nakao Y, Hiyama T. J. Am. Chem. Soc. 2009 131 6624.
37. Wu M.-S, Rayabarapu D. K, Cheng C.-H. J. Am. Chem. Soc. 2003 125 12426.
38. Nakao Y, Yada A, Ebata S, Hiyama T. J. Am. Chem. Soc. 2007 129 2428.
39. Watson M. P, Jacobsen E. N. J. Am. Chem. Soc. 2008 130 12594.
40. Percec V, Bae J.-Y, Zhao M, Hill D. H. J. Org. Chem. 1995 60 176.
41. Percec V, Bae J.-Y, Hill D. H. J. Org. Chem. 1995 60 1060.
42. Hirata Y, Yada A, Morita E, Nakao Y, Hiyama T, Ohashi M, Ogoshi S. J. Am. Chem. Soc. 2010 132 10070.
43. Yu D.-G, Yu M, Guan B.-T, Li B.-J, Zheng Y, Wu Z.-H, Shi Z.-J. Org. Lett. 2009 11 3374.
44. Nakai K, Kurahashi T, Matsubara S. J. Am. Chem. Soc. 2011 133 11066.
45. Patra T, Agasti S, Akanksha; Maiti D. Chem. Commun. 2013 49 69.
46. Tobisu M, Kita Y, Chatani N. J. Am. Chem. Soc. 2006 128 8152.
47. Nakao Y, Yukawa T, Hirata Y, Oda S, Satoh J, Hiyama T. J. Am. Chem. Soc. 2006 128 7116.
48. Nakao Y, Yada A, Ebata S, Hiyama T. J. Am. Chem. Soc. 2007 129 2428.
49. Hirata Y, Yukawa T, Kashihara N, Nakao Y, Hiyama T. J. Am. Chem. Soc. 2009 131 10964.
50. Nakao Y, Yada A, Hiyama T. J. Am. Chem. Soc. 2010 132 10024.
51. Luo F.-H, Chu C.-I, Cheng C.-H. Organometallics 1998 17 1025.
52. Sundermeier M, Zapf A, Beller M. Angew. Chem. Int. Ed. 2003 42 1661.
53. Wen Q, Jin J, Hu B, Lu P, Wang Y. RSC Adv. 2012 2 6167.
54. Tobisu M, Nakamura R, Kita Y, Chatani N. J. Am. Chem. Soc. 2009 131 3174.
55. Park E. J, Lee S, Chang S. J. Org. Chem. 2010 75 2760.
56. Jin J, Wen Q, Lu P, Wang Y. Chem. Commun. 2012 48 9933.
57. Song R.-J, Wu J.-C, Liu Y, Deng G.-B, Wu C.-Y, Wei W.-T, Li J.-H. Synlett 2012 2491.
58. Nakazawa H, Kamata K, Itazaki M. Chem. Commun. 2005 p. 4004.
59. Nakao Y, Hirata Y, Tanaka M, Hiyama T. Angew. Chem., Int. Ed. 2008 47 385.
60. Abla M, Yamamoto T. J. Org. Chem. 1997 532 267.
61. Garcia J. J, Jones W. D. Organometallics 2000 19 5544.
62. Garcia J. J, Brunkan N. M, Jones W. D. J. Am. Chem. Soc. 2002 124 9547.
63. Brunkan N. M, Brestensky D. M, Jones W. D. J. Am. Chem. Soc. 2004 126 3627.
64. García J. J, Arévalo A, Brunkan N. M, Jones W. D. Organometallics 2004 23 3997.
65. Atešin T. A, Li T, Lachaize S, Brennessel W. W, García J. J, Jones W. D. J. Am. Chem. Soc. 2007 129 7562.
66. Atešin T. A, Li T, Lachaize S, García J. J, Jones W. D. Organometallics 2008 27 3811.
67. Taw F. L, White P. S, Bergman R. G, Brookhart M. J. Am. Chem. Soc. 2002 124 4192.
68. Taw F. L, Mellows H, Brookhart M, Heinekey D. M. J. Am. Chem. Soc. 2002 124 5100.
69. Taw F. L, Mueller A. H, Bergman R. G, Brookhart M. J. Am. Chem. Soc. 2003 125 9808.
70. Ochiai M, Hashimoto H, Tobita H. Angew. Chem. Int. Ed. 2007 46 8192.
71. Marlin D. S, Olmstead M. M, Mascharak P. K. Angew. Chem. Int. Ed. 2001 113 4888.
72. Lu T, Zhuang X, Li Y. Chen S. J. Am. Chem. Soc. 2004 126 4760.
73. Li X, Sun H, Yu F, Flörke U, Klein H.-F. Organometallics 2006 25 4695.
74. Xu H, Williard P. G, Bernskoetter W. H. Organometallics 2012 31 1588.
75. Nakazawa H, Kawasaki T, Miyoshi K, Suresh C. H, Koga N. Organometallics 2004 23 117.
76. Churchill D, Shin J. H, Hascall T, Hahn J. M, Bridgewater B. M, Parkin G. Organometallics 1999 18 2403.
77. Liu Q.-X, Xu F.-B, Li Q.-S, Song H.-B, Zhang Z.-Z. Organometallics 2004 23 610.