Synthesis of aryl thiocyanates via copper-catalyzed aerobic oxidative cross-coupling between arylboronic acids and KSCN

Synlett

Volumn 24, Issue 11, 2013, Pages 1443-1447

  Sun, Nan ^a   Zhang, Han ^a   Mo, Weimin ^a   Hu, Baoxiang ^a   Shen, Zhenlu ^a   Hu, Xinquan ^a,b  

^a ZHEJIANG UNIVERSITY OF TECHNOLOGY   (China)

^b LANZHOU INSTITUTE OF CHEMICAL PHYSICS   (China)

Author keywords

aryl thiocyanates; arylboronic acids; copper acetate; oxidative cross coupling reaction; potassium thiocyanate

Indexed keywords

2 METHOXYPHENYL THIOCYANATE; 4 (METHOXYCARBONYL)PHENYL THIOCYANATE; 4 BROMOPHENYL THIOCYANATE; 4 FLUOROPHENYL THIOCYANATE; BORONIC ACID DERIVATIVE; COPPER ACETATE; OXYGEN; PHENYL THIOCYANATE; PICOLINE; PYRIDINE DERIVATIVE; THIOCYANATE POTASSIUM; THIOCYANIC ACID DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL MODIFICATION; CHEMICAL REACTION KINETICS; CROSS COUPLING REACTION; OXIDATIVE COUPLING; PHYSICAL CHEMISTRY; REACTION ANALYSIS; SYNTHESIS;

EID: 84877598578     PISSN: 09365214     EISSN: 14372096     Source Type: Journal    
DOI: 10.1055/s-0033-1338939     Document Type: Article

References (48)

1. Rao K. S., Wu T. S. Tetrahedron: 2012; 68 7735
2. Qiao J. X., Lam P. Y. S. Synthesis: 2011; 829
3. Chan D. M. T, Monaco K. L., Wang R. P., Winters M. P. Tetrahedron Lett.: 1998; 39 2933
4. Lam P. Y. S, Clark C. G., Saubern S., Adams J., Winters M. P., Chan D. M. T, Combs A. Tetrahedron Lett.: 1998; 39 2941
5. Novak P., Lishchynskyi A., Grushin V. V. Angew. Chem. Int. Ed.: 2012; 51 7767
6. Matsuda N., Hirano K., Satoh T., Miura M. Angew. Chem. Int. Ed.: 2012; 51 3642
7. Li J. H., Benard S., Neuville L., Zhu J. P. Org. Lett.: 2012; 14 5980
8. Inamoto K., Nozawa K., Kadokawa J., Kondo Y. Tetrahedron: 2012; 68 7794
9. Kianmehr E., Baghersad M. H. Adv. Synth. Catal.: 2011; 353 2599
10. Zhang G. Y., Zhang L. L., Hu M. L., Cheng J. A. Adv. Synth. Catal.: 2011; 353 291
11. Li Y., Gao L. X., Han F. S. Chem. Eur. J.: 2010; 16 7969
12. Zhang L. L., Zhang G. Y., Zhang M. L., Cheng J. A. J. Org. Chem.: 2010; 75 7472
13. Rao H. H., Fu H., Jiang Y. Y., Zhao Y. F. Angew. Chem. Int. Ed.: 2009; 48 1114
14. He C., Chen C., Cheng J., Liu C., Liu W., Li Q., Lei A. W. Angew. Chem. Int. Ed.: 2008; 47 6414
15. Xu H. J., Zhao Y. Q., Feng T., Feng Y. S. J. Org. Chem.: 2012; 77 2878
16. Herradura P. S., Pendola K. A., Guy R. K. Org. Lett.: 2000; 2 2019
17. Luo P. S., Wang F., Li J. H., Tang R. Y., Zhong P. Synthesis: 2009; 921
18. Taniguchi N. J. Org. Chem.: 2007; 72 1241
19. Taniguchi N. Synlett: 2006; 1351
20. Erian A. W., Sherif S. M. Tetrahedron: 1999; 55 7957
21. Zheng W. X., Ariafard A., Lin Z. Y. Organometallics: 2008; 27 246
22. Laufer S. A., Liedtke A. J. Tetrahedron Lett.: 2006; 47 7199
23. Demko Z. P., Sharpless K. B. Org. Lett.: 2001; 3 4091
24. Billard T., Langlois B. R., Medebielle M. Tetrahedron Lett.: 2001; 42 3463
25. Toste F. D., Laronde F., Still I. W. J. Tetrahedron Lett.: 1995; 36 2949
26. Yasman Y., Edrada R. A., Wray V., Proksch P. J. Nat. Prod.: 2003; 66 1512
27. Elhalem E., Bailey B. N., Docampo R., Ujvary I., Szajnman S. H., Rodriguez J. B. J. Med. Chem.: 2002; 45 3984
28. Alaimo R. J., Pelosi S. S., Hatton C. J., Gray J. E. J. Med. Chem.: 1974; 17 775
29. Mokhtari B., Azadi R., Mardani E. Tetrahedron Lett.: 2012; 53 491
30. Reddy B. V. S, Reddy S. M. S, Madan C. Tetrahedron Lett.: 2011; 52 1432
31. Bisogno F. R., Cuetos A., Lavandera I., Gotor V. Green Chem.: 2009; 11 452
32. Iranpoor N., Firouzabadi H., Nowrouzi N. Tetrahedron: 2006; 62 5498; and the references cited in these papers
33. Guy R. G. In The Chemistry of Functional Groups: The Chemistry of Cyanates and Their Thio Derivatives. Patai S. Wiley New York: 1977; Part 2 Chap. 18
34. Pilgram K., Phillips D. D. J. Org. Chem.: 1965; 30 2388
35. Zarchi M. A. K, Ebrahimi N. Phosphorus, Sulfur Silicon Relat. Elem.: 2012; 187 1226
36. Beletskaya I. P., Sigeev A. S., Peregudov A. S., Petrovskii P. V. Mendeleev Commun.: 2006; 250
37. Barbero M., Degani I., Diulgheroff N., Dughera S., Fochi R. Synthesis: 2001; 585
38. Khazaei A., Zolfigol M. A., Safaiee M., Mokhlesi M., Donyadari E., Shiri M., Kruger H. G. Catal. Commun.: 2012; 26 34
39. Khazaei A., Zolfigol M. A., Mokhlesi M., Panah F. D., Sajjadifar S. Helv. Chim. Acta: 2012; 95 106
40. Iranpoor N., Firouzabadi H., Khalili D., Shahin R. Tetrahedron Lett.: 2010; 51 3508
41. Bhalerao D. S., Akamanchi K. G. Synlett: 2007; 2952
42. Toste F. D., Destefano V., Still I. W. J. Synth. Commun.: 1995; 25 1277
43. Wang Y. F., Zhou Y., Wang J. R., Liu L., Guo Q. X. Chin. Chem. Lett.: 2006; 17 1283
44. Suzuki H., Abe H. Synth. Commun.: 1996; 26 3413
45. Clark J. H., Jones C. W., Duke C. V. A, Miller J. M. J. Chem. Soc., Chem. Commun.: 1989; 81
46. Still I. W. J, Watson I. D. G. Synth. Commun.: 2001; 31 1355
47. Kagabu S., Sawahara K., Maehara M., Ichihashi S., Saito K. Chem. Pharm. Bull.: 1991; 39 784
48. Harpp D. H., Friedlander B. T., Smith R. A. Synthesis: 1979; 181