Chloro, difluoromethylation and chloro, carbomethoxydifluoromethylation: Reaction of radicals derived from RfSO2Cl with unactivated alkenes under metal-free conditions

Journal of Organic Chemistry

Volumn 80, Issue 2, 2015, Pages 1264-1268

  Thomoson, Charles S ^a   Tang, Xiao Jun ^a   Dolbier, William R ^a  

^a University of Florida   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CHLORINE COMPOUNDS; HYDROCARBONS; SULFUR DIOXIDE;

ATOM TRANSFER RADICAL ADDITION; METAL-FREE CONDITIONS; SULFONYL CHLORIDES;

FREE RADICAL REACTIONS;

ALKENE DERIVATIVE; BENZENE DERIVATIVE; CHLORIDE; ORGANOCHLORINE DERIVATIVE; ORGANOFLUORINE DERIVATIVE;

ADDITION REACTION; ARTICLE; ATOM TRANSFER RADICAL ADDITION; CATALYST; CHLORINATION; METHYLATION; RADICAL REACTION; STEREOISOMERISM;

EID: 84921416833     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo502595g     Document Type: Article

References (58)

1. Kharasch, M. S.; Jensen, E. V.; Urry, W. H. Science 1945, 102, 128
2. OHagan, D. Chem. Soc. Rev. 2008, 37, 308-319
3. Dolbier, W. R., Jr. Chem. Rev. 1996, 96, 1557-1584
4. Dolbier, W. R., Jr. In Topics in Current Chemistry; Chambers, R. D., Ed.; Springer: Berlin, 1997; Vol. 192, pp 97-163.
5. Charpentier, J.; Fruh, N.; Togni, A. Chem. Rev. 2014, dx.doi.org/10.1021/cr500223h
6. Koike, T.; Akita, M. J. Fluorine Chem. 2014, 167, 30-36
7. Egami, H.; Sodeoka, M. Angew. Chem., Int. Ed. 2014, 53, 8294-8308
8. Ni, C.; Hu, N.; Hu, J. Chem. Rev. 2014, dx.doi.org/10.1021/cr5002386
9. Janson, P. G.; Ghoneim, I.; Ilchenko, N. O.; Szabó, K. J. Org. Lett. 2012, 14, 2882-2885
10. Egami, H.; Shimizu, R.; Sodeoka, M. Tetrahedron Lett. 2012, 53, 5503-5506
11. Ilchenko, N. O.; Janson, P. G.; Szabó, K. J. J. Org. Chem. 2013, 78, 11087-11091
12. He, Y.-T.; Li, L.-H.; Yang, Y.-F.; Zhou, Z.-Z.; Hua, H.-L.; Liu, X.-Y.; Liang, Y.-M. Org. Lett. 2013, 16, 270-273
13. Wang, F.; Qi, X.; Liang, Z.; Chen, P.; Liu, G. Angew. Chem., Int. Ed. 2014, 53, 1881-1884
14. Lu, D.-F.; Zhu, C.-L.; Xu, H. Chem. Sci. 2013, 4, 2478-2482
15. Carboni, A.; Dagousset, G.; Magnier, E.; Masson, G. Org. Lett. 2014, 16, 1240-1243
16. Yasu, Y.; Koike, T.; Akita, M. Org. Lett. 2013, 15, 2136-2139
17. Egami, H.; Kawamura, S.; Miyazaki, A.; Sodeoka, M. Angew. Chem., Int. Ed. 2013, 52, 7841-7844
18. Lin, J.-S.; Xiong, Y.-P.; Ma, C.-L; Zhao, L.-J.; Tan, B.; Liu, X.-Y. Chem.-Eur. J. 2014, 20, 1332-1340
19. Wang, F.; Qi, X.; Liang, Z.; Chen, P.; Liu, G. Angew. Chem., Int. Ed. 2014, 53, 1881-1886
20. Jiang, X.-Y.; Qing, F.-L. Angew. Chem., Int. Ed. 2013, 52, 14177-14180
21. Deb, A.; Manna, S.; Modak, A.; Patra, T.; Maity, S.; Maiti, D. Angew. Chem., Int. Ed. 2013, 52, 9747-9750
22. Hang, Z.; Li, Z.; Liu, Z.-Q. Org. Lett. 2014, 16, 3648-3651
23. Oh, S. H.; Malpani, Y. R.; Ha, N.; Jung, Y.-S.; Han, S. B. Org. Lett. 2014, 16, 1310-1313
24. Huang, W.-Y.; Chen, J.-L.; Hu, L.-Q. Bull. Soc. Chim. Fr. 1986, 881-884
25. Huang, W.-Y.; Chen, J.-L.; Hu, L.-Q. Acta Chim. Sin. 1988, 46, 895
26. Huang, W.-Y.; Lu, L. Chin. J. Chem. 1992, 10, 268-271
27. Huang, W.-Y.; Zhang, H.-Z. Chin. J. Chem. 1992, 10, 544-547
28. Billard, T.; Roques, N.; Langlois, B. R. J. Org. Chem. 1999, 64, 3813-3816
29. Li, Y.; Studer, A. Angew. Chem., Int. Ed. 2012, 51, 8221-8224
30. Fuchikami, T.; Shibata, Y.; Urata, H. Chem. Lett. 1987, 521-524
31. Kim, E.; Choi, S.; Kim, H.; Cho, E. J. Chem.-Eur. J. 2013, 19, 6209-6212
32. Lui, X.; Xu, C.; Wang, M.; Lui, Q. Chem. Rev. 2014, dx.doi.org/10.1021/cr400473a
33. Salomon, P.; Zard, S. Z. Org. Lett. 2014, 16, 2926-2929
34. OHara, F.; Blackmond, D. G.; Baran, P. S. J. Am. Chem. Soc. 2013, 135, 12122-12134
35. Kirk, K. L. Org. Process Res. Dev. 2008, 12, 305
36. Prakash, G. K. S.; Chacko, S. Curr. Opin. Drug Discovery Dev. 2008, 11, 793
37. Cao, P.; Duan, J.-X.; Chen, Q. Y. J. Chem. Soc., Chem. Commun. 1994, 737-738
38. Gonzalez, J.; Foti, C.; Elsheimer, S. J. Org. Chem. 1991, 56, 4322-4325
39. Miethchen, R.; Hein, M.; Reinke, H. Eur. J. Org. Chem. 1998, 63, 919-923
40. Megert, A.; Meithchen, R.; Hein, M.; Reinke, H. Synthesis 2005, 1850-1853
41. Reutrakul, V.; Thongpausanwong, T.; Tuchinda, P.; Kuhabarn, C.; Pohmakot, M. J. Org. Chem. 2004, 69, 6913-6917
42. Li, Y.; Lui, J.; Zhang, L.; Zhu, L.; Hu, J. J. Org. Chem. 2007, 72, 5824-5827
43. Prakash, G. K. S.; Hu, J.; Wang, Y.; Olah, G. A. Org. Lett. 2004, 6, 4315-4318
44. Ye, J. D.; Liao, X.; Precirilli, J. A. J. Org. Chem. 2005, 70, 7902-7910
45. Stahly, G. P. J. Fluorine Chem. 1989, 43, 53-66
46. Ni, C.; Hu, J. Tetrahedron Lett. 2005, 46, 8273-8277
47. Yang, Y.; Xu, J.; You, Z.; Xu, X.; Qiu, X.; Qing, F. L. Org. Lett. 2007, 9, 5437-5440
48. Otsuka, T.; Ishii, A.; Dub, P. A.; Ikariya, T. J. Am. Chem. Soc. 2013, 135, 9600-9604
49. Ueno, R.; Osama, H.; Oda, T. Eur. Patent EP435443A2.
50. Nguyen, J. D.; Tucker, J. W.; Konieczynska, M. D.; Stephenson, C. R. J. J. Am. Chem. Soc. 2011, 133, 4160-4163
51. Tucker, J. W.; Zhang, Y.; Jamison, T. F.; Stephenson, C. R. J. Angew. Chem., Int. Ed. 2012, 51, 4144-4147
52. Sato, O.; Ando, K. J. Fluorine Chem. 2004, 125, 509-515
53. Yang, Z.-Y.; Burton, D. J. J. Org. Chem. 1992, 57, 5144-5149
54. Yang, Z.-Y.; Burton, D. J. J. Fluorine Chem. 1989, 45, 435-439
55. Yang, X.; Wang, Z.; Zhu, Y.; Fang, X.; Yang, X.; Wu, F.; Shen, Y. J. Fluorine Chem. 2007, 128, 1046-1051
56. Kitagawa, O.; Miura, A.; Kobayashi, Y.; Taguchi, T. Chem. Lett. 1990, 6, 1011-1014
57. Xiao, F.; Wu, F.; Shen, Y.; Zhou, L. J. Fluorine Chem. 2005, 126, 63-67
58. Tang, X. J.; Thomoson, C. S.; Dolbier, W. R., Jr. Org. Lett. 2014, 16, 4594-4597