Rhodium-catalyzed direct C-H bond cyanation of arenes with isocyanide

Journal of Organic Chemistry

Volumn 79, Issue 7, 2014, Pages 3228-3237

  Hong, Xiaohu ^a   Wang, Hao ^a   Qian, Guangyin ^a   Tan, Qitao ^a   Xu, Bin ^a,b,c  

^a SHANGHAI UNIVERSITY   (China)

^b SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

^c EAST CHINA NORMAL UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

AROMATIC COMPOUNDS; CATALYSIS; FUNCTIONAL GROUPS; REGIOSELECTIVITY; RHODIUM;

C-H BOND; CYANATION; ISOCYANIDES; REGIO-SELECTIVE; RHODIUM-CATALYZED; TERT-BUTYL ISOCYANIDE;

CYANIDES;

1 (PYRIMIDIN 2 YL) 2 NAPHTHONITRILE; 2 (4 PHENYLPYRIMIDIN 2 YL)BENZONITRILE; 2 (5 ETHYLPYRIMIDIN 2 YL)BENZONITRILE; 2 (PYRIMIDIN 2 YL) 5 (TRIFLUOROMETHYL)BENZONITRILE; 2 PYRIMIDIN 2 YL BENZONITRILE; 3 (PYRIMIDIN 2 YL) 2 NAPHTHONITRILE; 3 CYANO 4 PYRMIDIN 2 YL BENZOIC ACID ETHYL ESTER; 3 METHOXY 2,5 DIMETHYL 6 (PYRMIDIN 2 YL)BENZONITRILE; 3 METHYL 2 (PYRIMIDIN 2 YL)BENZONITRILE; 4 CHLORO 2 (PYRIMIDIN 2 YL)BENZONITRILE; 4 CYANO 3 (PYRIMIDIN 2 YL)PHENYL 4 METHYLBENZENESULFONATE; 4 FLUORO 2 (PYRIMDIN 2 YL)BENZONITRILE; 4 METHYL 2 (PYRMIDIN2 YL)BENZONITRILE; 4,5 DIMETHOXY 2 PYRIMIDIN 2 YL BENZONITRILE; 5 CHLORO 2 PYRIMIDIN 2 YL BENZONITRILE; 5 ETHOXY 2 (PYRIMIDIN 2 YL)BENZONITRILE; 5 FLUORO 2 (PYRIMIDIN 2 YL)BENZONITRILE; 5 METHOXY 2 PYRIMIDIN 2 YL BENZONITRILE; 5 METHOXY 2 [4 (4 METHOXYPHENYL)PYRIMIDIN 2 YL] BENZONITRILE; 5 METHYL 2 PYRIMIDIN 2 YL BENZONITRILE; CARBON; CYANIDE; CYCLOALKENE; HYDROGEN; N [2 (2 CYANOPHENYL)PYRIMIDIN 4 YL]ACETAMIDE; NITRILE; NITROGEN; POLYCYCLIC AROMATIC HYDROCARBON; RHODIUM; TOLUENE 4 SULFONIC ACID 3 CYANO 4 PYRIMIDIN 2 YL PHENYL ESTER; UNCLASSIFIED DRUG; CYCLOALKANE DERIVATIVE; HETEROCYCLIC COMPOUND; TERT-BUTYL ISOCYANIDE;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CATALYSIS; COVALENT BOND; CYANATION; ELECTROSPRAY; PROTON NUCLEAR MAGNETIC RESONANCE; SYNTHESIS; CHEMICAL STRUCTURE; CHEMISTRY; HYDROGEN BOND;

CATALYSIS; CYANIDES; CYCLOPARAFFINS; HETEROCYCLIC COMPOUNDS; HYDROGEN BONDING; MOLECULAR STRUCTURE; NITRILES; RHODIUM;

EID: 84898077896     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo500087g     Document Type: Article

References (49)

1. Kleemann, A., Engel, J., Kutscher, B., and Reichert, D. Pharmaceutical Substances: Syntheses, Patents, Applications, 4 th ed.; Georg Thieme: Stuttgart, Germany, 2001.
2. Larock, R. C. Comprehensive Organic Transformations: A Guide to Functional Group Preparations; John Wiley & Sons: New York, 1999.
3. Rappoport, Z. Chemistry of the Cyano Group; John Wiley & Sons: London, 1970.
4. Galli, C. Chem. Rev. 1988, 88, 765
5. Lindley, J. Tetrahedron. 1984, 40, 1433
6. Ushkov, A. V.; Grushin, V. V. J. Am. Chem. Soc. 2011, 133, 10999
7. Yeung, P. Y.; So, C. M.; Lau, C. P.; Kwong, F. Y. Org. Lett. 2011, 13, 648
8. Zhang, D.; Sun, H.; Zhang, L.; Zhou, Y.; Li, C.; Jiang, H.; Chen, K.; Liu, H. Chem. Commun. 2012, 48, 2909
9. Schareina, T.; Zapf, A.; Beller, M. Chem. Commun. 2004, 1388
10. Zheng, S.; Yu, C.; Shen, Z. Org. Lett. 2012, 14, 3644
11. Anbarasan, P.; Neumann, H.; Beller, M. Chem.-Eur. J. 2011, 17, 4217
12. Do, H.-Q.; Daugulis, O. Org. Lett. 2010, 12, 2517
13. Rueping, M.; Zhu, S.; Koenigs, R. M. Chem. Commun. 2011, 47, 12709
14. Jia, X.; Yang, D.; Zhang, S.; Cheng, J. Org. Lett. 2009, 11, 4716
15. Jia, X.; Yang, D.; Wang, W.; Luo, F.; Cheng, J. J. Org. Chem. 2009, 74, 9470
16. Yan, G.; Zhang, Y.; Wang, J.; Kuang, C. Org. Lett. 2010, 12, 1052
17. Zhang, Y.; Peng, H.; Zhang, M.; Cheng, Y.; Zhu, C. Chem. Commun. 2011, 47, 2354
18. Kamijo, S.; Hoshikawa, T.; Inoue, M. Org. Lett. 2011, 13, 5928
19. Qin, C.; Jiao, N. J. Am. Chem. Soc. 2010, 132, 15893
20. Verma, S.; Jain, S. L.; Sain, B. Catal. Lett. 2011, 141, 882
21. Chen, X.; Hao, X.-S.; Goodhue, C. E.; Yu, J.-Q. J. Am. Chem. Soc. 2006, 128, 6790
22. Kim, J.; Chang, S. J. Am. Chem. Soc. 2010, 132, 10272
23. Ding, S.; Jiao, N. J. Am. Chem. Soc. 2011, 133, 12374
24. Ren, X.; Chen, J.; Chen, F.; Cheng, J. Chem. Commun. 2011, 47, 6725
25. Yang, Y.; Zhang, Y.; Wang, J. Org. Lett. 2011, 13, 5608
26. Gong, T.-J.; Xiao, B.; Cheng, W.-M.; Su, W.; Xu, J.; Liu, Z.-J.; Liu, L.; Fu, Y. J. Am. Chem. Soc. 2013, 135, 10630
27. Okamoto, K.; Watanabe, M.; Murai, M.; Hatano, R.; Ohe, K. Chem. Commun. 2012, 48, 3127
28. Jin, J.; Wen, Q.; Lu, P.; Wang, Y. Chem. Commun. 2012, 48, 9933
29. Xu, H.; Liu, P.-T.; Li, Y.-H.; Han, F.-S. Org. Lett. 2013, 15, 3354
30. Kim, J.; Kim, H. J.; Chang, S. Angew. Chem., Int. Ed. 2012, 51, 11948
31. Xu, S.; Huang, X.; Hong, X.; Xu, B. Org. Lett. 2012, 14, 4614
32. Peng, J.; Zhao, J.; Hu, Z.; Liang, D.; Huang, J.; Zhu, Q. Org. Lett. 2012, 14, 4966
33. Chaitanya, M.; Yadagiri, D.; Anbarasan, P. Org. Lett. 2013, 15, 4960
34. Joule, J. A.; Mills, K. Heterocyclic Chemistry, 5 th ed.; Blackwell Publishing: Cambridge, 2000; pp 249-288.
35. Blackburn, M. J.; Gait, G. M.; Loakes, D.; Williams, D. M. In Nucleic Acids in Chemistry and Biology, 3 rd ed.; Oxford University Press: Oxford, 2006; Chapter 8, pp 295-360.
36. Song, B.; Zheng, X.; Mo, J.; Xu, B. Adv. Synth. Catal. 2010, 352, 329
37. Zheng, X.; Song, B.; Li, G.; Liu, B.; Deng, H.; Xu, B. Tetrahedron Lett. 2010, 51, 6641
38. Zheng, X.; Song, B.; Xu, B. Eur. J. Org. Chem. 2010, 2010, 4376
39. Huang, X. M.; Xu, S. G.; Tan, Q. T.; Gao, M. C.; Li, M. J.; Xu, B. Chem. Commun. 2014, 50, 1465
40. Burrell, A. J. M; Martinez, C. A; Mcdaid, P. O.; ONeill, P. M; Wong, J. W. WO/2012/025861 A1, 2012.
41. Nicolaou, K. C.; Gray, D. L. F.; Montagnon, T.; Harrison, S. T. Angew. Chem., Int. Ed. 2002, 41, 996
42. Hudlicky, J. R.; Werner, L.; Semak, V.; Simionescu, R.; Hudlicky, T. Can. J. Chem. 2011, 89, 535
43. Sasaki, T.; Eguchi, S.; Katada, T. J. Org. Chem. 1974, 39, 1239
44. Meier, M.; Rüchardt, C. Tetrahedron Lett. 1983, 24, 4671
45. Colby, D. A.; Bergman, R. G.; Ellman, J. A. Chem. Rev. 2010, 110, 624
46. Zhu, C.; Xie, W.; Falck, J. R. Chem.-Eur. J. 2011, 17, 12591
47. Kang, D. M.; Kang, J.-W.; Park, J. W.; Jung, S. O.; Lee, S.-H.; Park, H.-D.; Kim, Y.-H.; Shin, S. C.; Kim, J.-J.; Kwon, S.-K. Adv. Mater. 2008, 20, 2003
48. Feng, Y. S.; Moses, A.; Zhong, Y.-L. WO/2012/058129 A1, 20120503, 2012.
49. Branstetter, B. J.; Letavic, M. A.; Ly, K. S.; Rudolph, D. A.; Savall, B. M.; Shah, C. R.; Shireman, B. T. WO/2011/050202 A1, 20110428, 2011.