Cyanoacetic Acid as a Masked Electrophile: Transition-Metal-Free Cyanomethylation of Amines and Carboxylic Acids

Chemistry - A European Journal

Volumn 21, Issue 50, 2015, Pages 18333-18337

  Wang, Hongxiang ^a   Shao, Ying ^a,b   Zheng, Hao ^b   Wang, Hanghang ^a   Cheng, Jiang ^b   Wan, Xiaobing ^a  

^a SOOCHOW UNIVERSITY   (China)

^b CHANGZHOU UNIVERSITY   (China)

Author keywords

cyanomethylation; decarboxylation; iodination; metal free synthesis; nucleophilic substitution; aminonitriles

Indexed keywords

AMINES; CARBOXYLATION; CARBOXYLIC ACIDS; HALOGENATION;

AMINONITRILES; CYANOMETHYLATION; DECARBOXYLATION; IODINATION; METAL-FREE SYNTHESIS; NUCLEOPHILIC SUBSTITUTIONS;

TRANSITION METALS;

EID: 84949309962     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.201502733     Document Type: Article

References (105)

1. D. Enders, J. P. Shilvock, Chem. Soc. Rev. 2000, 29, 359.
2. M. Makosza, Chem. Soc. Rev. 2010, 39, 2855;
3. J. Velcicky, A. Soicke, R. Steiner, H.-G. Schmalz, J. Am. Chem. Soc. 2011, 133, 6948;
4. T. Jinzaki, M. Arakawa, H. Kinoshita, J. Ichikawa, K. Miura, Org. Lett. 2013, 15, 3750;
5. H. Yi, X. Zhang, C. Qin, Z. Liao, J. Liu, A. Lei, Adv. Synth. Catal. 2014, 356, 2873.
6. D. A. Culkin, J. F. Hartwig, J. Am. Chem. Soc. 2002, 124, 9330;
7. J. You, J. G. Verkade, Angew. Chem. Int. Ed. 2003, 42, 5051;
8. Angew. Chem. 2003, 115, 5205;
9. Y. Suto, N. Kumagai, S. Matsunaga, M. Kanai, M. Shibasaki, Org. Lett. 2003, 5, 3147;
10. N. Kumagai, S. Matsunaga, M. Shibasaki, J. Am. Chem. Soc. 2004, 126, 13632;
11. T. Wu, X. Mu, G. Liu, Angew. Chem. Int. Ed. 2011, 50, 12578;
12. Angew. Chem. 2011, 123, 12786;
13. S. Chakraborty, Y. J. Patel, J. A. Krause, H. Guan, Angew. Chem. Int. Ed. 2013, 52, 7523;
14. Angew. Chem. 2013, 125, 7671;
15. H. Yoshida, Y. Fujimura, H. Yuzawa, J. Kumagai, T. Yoshida, Chem. Commun. 2013, 49, 3793;
16. 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;
17. A. Bunescu, Q. Wang, J. Zhu, Chem. Eur. J. 2014, 20, 14633;
18. G. Wang, A. Zhou, J. Wang, R. Hu, S. Yang, Org. Lett. 2013, 15, 5270;
19. J. Li, Z. Wang, N. Wu, G. Gao, J. You, Chem. Commun. 2014, 50, 15049;
20. L. Yin, M. Kanai, M. Shibasaki, J. Am. Chem. Soc. 2009, 131, 9610;
21. A. Bunescu, Q. Wang, J. Zhu, Angew. Chem. Int. Ed. 2015, 54, 3132;
22. Angew. Chem. 2015, 127, 3175;
23. T. Deng, H. Wang, C. Cai, Eur. J. Org. Chem. 2014, 7259;
24. C. Pan, H. Zhang, C. Zhu, Org. Biomol. Chem. 2015, 13, 361;
25. T. Yamashita, J. Org. Chem. 1996, 61, 6438;
26. J. Zhang, W. Wu, X. Ji, S. Cao, RSC Adv. 2015, 5, 20562;
27. J. You, J. G. Verkade, J. Org. Chem. 2003, 68, 8003.
28. L. Wu, J. F. Hartwig, J. Am. Chem. Soc. 2005, 127, 15824;
29. S. Matsukawa, E. Kitazaki, Tetrahedron Lett. 2008, 49, 2982;
30. Y. C. Fan, G. F. Du, W. F. Sun, W. Kang, L. He, Tetrahedron Lett. 2012, 53, 2231;
31. F. Diaba, C. Houerou, M. G. Dubois, P. Gerval, J. Org. Chem. 2000, 65, 907;
32. C. Verrier, S. Oudeyer, I. Dez, V. Levacher, Tetrahedron Lett. 2012, 53, 1958.
33. A. Nortcliffe, N. P. Botting, D. O'Hagan, Org. Biomol. Chem. 2013, 11, 4657;
34. S. Roy, A. Eastman, G. W. Gribble, Tetrahedron 2006, 62, 7838.
35. P. J. Lindsay-Scott, A. Clarke, J. Richardson, Org. Lett. 2015, 17, 476.
36. R. Shang, D.-S. Ji, L. Chu, Y. Fu, L. Liu, Angew. Chem. Int. Ed. 2011, 50, 4470;
37. Angew. Chem. 2011, 123, 4562;
38. P. Y. Yeung, K. H. Chung, F. Y. Kwong, Org. Lett. 2011, 13, 2912;
39. R. Shang, Z. Huang, X. Xiao, X. Lu, Y. Fu, L. Liu, Adv. Synth. Catal. 2012, 354, 2465;
40. L. Yin, M. Kanai, M. Shibasaki, Tetrehedron 2012, 68, 3497;
41. K. Hyodo, M. Kondo, Y. Funahashi, S. Nakamura, Chem. Eur. J. 2013, 19, 4128;
42. Q. Ren, J. Huang, L. Wang, W. Li, H. Liu, X. Jiang, J. Wang, ACS Catal. 2012, 2, 2622;
43. V. P. R. Gajulapalli, P. Vinayagam, V. Kesavan, Org. Biomol. Chem. 2014, 12, 4186;
44. A. Recio III, J. D. Heinzman, J. A. Tunge, Chem. Commun. 2012, 48, 142;
45. A. Recio III, J. A. Tunge, Org. Lett. 2009, 11, 5630.
46. Recently, we reported various oxidation reactions using TBAI/TBHP, see:
47. L. Chen, E. Shi, Z. Liu, S. Chen, W. Wei, H. Li, K. Xu, X. Wan, Chem. Eur. J. 2011, 17, 4085;
48. W. Wei, C. Zhang, Y. Xu, X. Wan, Chem. Commun. 2011, 47, 10827;
49. S. Chen, Y. Xu, X. Wan, Org. Lett. 2011, 13, 6152;
50. Z. Liu, J. Zhang, S. Chen, E. Shi, Y. Xu, X. Wan, Angew. Chem. Int. Ed. 2012, 51, 3231;
51. Angew. Chem. 2012, 124, 3285;
52. E. Shi, Y. Shao, S. Chen, H. Hu, Z. Liu, J. Zhang, X. Wan, Org. Lett. 2012, 14, 3384;
53. J. Zhang, J. Jiang, Y. Li, X. Wan, J. Org. Chem. 2013, 78, 11366;
54. C. Zhang, C. Liu, Y. Shao, X. Bao, X. Wan, Chem. Eur. J. 2013, 19, 17917.
55. L. J. Goossen, G. Deng, L. M. Levy, Science 2006, 313, 662;
56. S. Bhadra, W. I. Dzik, L. J. Goossen, J. Am. Chem. Soc. 2012, 134, 9938;
57. S. Bhadra, W. I. Dzik, L. J. Goossen, Angew. Chem. Int. Ed. 2013, 52, 2959;
58. Angew. Chem. 2013, 125, 3031.
59. A. G. Myers, D. Tanaka, M. R. Mannion, J. Am. Chem. Soc. 2002, 124, 11250;
60. D. Tanaka, A. G. Myers, Org. Lett. 2004, 6, 433;
61. D. Tanaka, S. P. Romeril, A. G. Myers, J. Am. Chem. Soc. 2005, 127, 10323.
62. E. C. Burger, J. A. Tunge, J. Am. Chem. Soc. 2006, 128, 10002;
63. R. Jana, J. J. Partridge, J. A. Tunge, Angew. Chem. Int. Ed. 2011, 50, 5157;
64. Angew. Chem. 2011, 123, 5263;
65. S. B. Lang, K. M. O'Nele, J. A. Tunge, J. Am. Chem. Soc. 2014, 136, 13606.
66. Some recent examples reported by others, see:
67. P. Hu, M. Zhang, X. Jie, W. Su, Angew. Chem. Int. Ed. 2012, 51, 227;
68. Angew. Chem. 2012, 124, 231;
69. A. Shard, N. Sharma, R. Bharti, S. Dadhwal, R. Kumar, A. K. Sinha, Angew. Chem. Int. Ed. 2012, 51, 12250;
70. Angew. Chem. 2012, 124, 12416;
71. D. L. Priebbenow, P. Becker, C. Bolm, Org. Lett. 2013, 15, 6155;
72. Y. singjunla, J. Baudoux, J. Rouden, Org. Lett. 2013, 15, 5770;
73. L. Chu, C. Ohta, Z. Zuo, D. W. C. MacMillan, J. Am. Chem. Soc. 2014, 136, 10886;
74. P. Klahn, H. Erhardt, A. Kotthaus, S. F. Kirsch, Angew. Chem. Int. Ed. 2014, 53, 7913;
75. Angew. Chem. 2014, 126, 8047;
76. H.-X. Zhang, J. Nie, H. Cai, J.-A. Ma, Org. Lett. 2014, 16, 2542;
77. C. Li, B. Breit, J. Am. Chem. Soc. 2014, 136, 862;
78. P. Forgione, M.-C. Brochu, M. St-Onge, K. H. Thesen, M. D. Bailey, F. Bilodeau, J. Am. Chem. Soc. 2006, 128, 11350.
79. J. W. Daly, B. Witkop, P. Bommer, K. Biemann, J. Am. Chem. Soc. 1965, 87, 124;
80. T. Tokuyama, J. Daly, B. Witkop, I. L. Karle, J. Karle, J. Am. Chem. Soc. 1968, 90, 1917;
81. D. Starling, J. Cell. Sci. 1976, 20, 79;
82. N. Funato, H. Takayanagi, Y. Konda, Y. Toda, Y. Harigaya, Y. Iwai, S. O¯mura, Tetrahedron Lett. 1994, 35, 1251;
83. K. Ishiuchi, T. Kubota, T. Hoshino, Y. Obara, N. Nakahata, J. Kobayashi, Bioorg. Med. Chem. 2006, 14, 5995;
84. S. B. Jones, B. Simmons, A. Mastracchio, D. W. C. MacMillan, Nature 2011, 475, 183.
85. For a review see:, M. North, in Comprehensive Organic Functional Group Transformations Vol. 3, (Eds.:, A. R. Katritzky, O. Meth-Cohn, C. W. Rees, G. Pattenden,), Pergamon, Oxford (UK), 1995, pp. 611-617.
86. M. North, Angew. Chem. Int. Ed. 2004, 43, 4126;
87. Angew. Chem. 2004, 116, 4218;
88. S.-I. Murahashi, N. Komiya, H. Terai, T. Nakae, J. Am. Chem. Soc. 2003, 125, 15312;
89. S.-I. Murahashi, T. Nakae, H. Terai, N. Komiya, J. Am. Chem. Soc. 2008, 130, 11005;
90. M. Rueping, J. Zoller, D. C. Fabry, K. Poscharny, R. M. Koenigs, T. e. Weirich, J. Mayer, Chem. Eur. J. 2012, 18, 3478;
91. D. B. Freeman, L. Frust, A. G. Condie, C. R. J. Stephenson, Org. Lett. 2012, 14, 94;
92. P. Liu, Y. Liu, E. L.-M. Wong, S. Xiang, C.-M. Che, Chem. Sci. 2011, 2, 2187.
93. W. Han, A. R. Ofial, Chem. Commun. 2009, 45, 5024;
94. Y. Zhang, H. Peng, M. Zhang, Y. Cheng, C. Zhu, Chem. Commun. 2011, 47, 2354;
95. M. G. Dekamin, M. Azimoshan, L. Ramezani, Green Chem. 2013, 15, 811;
96. L. Liu, Z. Wang, X. Fu, C.-H. Yan, Org. Lett. 2012, 14, 5692;
97. D. Chaturvedi, A. K. Chaturvedi, P. K. Dwivedi, N. Mishra, Synlett 2013, 24, 33;
98. B. Nammalwar, C. Fortenberry, R. A. Bunce, Tetrahedron Lett. 2014, 55, 379;
99. A. Wagner, W. Han, P. Mayer, A. R. Ofial, Adv. Synth. Catal. 2013, 355, 3058.
100. K. H. V. Reddy, G. Satish, V. P. Reddy, B. S. P. A. Kumar, Y. V. D. Nageswar, RSC Adv. 2012, 2, 11084.
101. S. I. Murahashi, T. Naota, K. Yonemura, J. Am. Chem. Soc. 1988, 110, 8256;
102. Y. Li, F. Jia, Z. Li, Chem. Eur. J. 2013, 19, 82;
103. J. Zhang, Y. Shao, Y. Wang, H. Li, D. Xu, X. Wan, Org. Biomol. Chem. 2015, 13, 3982;
104. C. Liu, E. Shi, F. Xu, Q. Luo, H. Wang, J. Chen, X. Wan, Chem. Commun. 2015, 51, 1214.
105. J. Zhang, J. Jiang, Y. Li, Y. Zhao, X. Wan, Org. Lett. 2013, 15, 3222.