Silver-Mediated N -Trifluoromethylation of Sulfoximines

Organic Letters

Volumn 17, Issue 12, 2015, Pages 3166-3169

  Teng, Fan ^a   Cheng, Jiang ^a,b   Bolm, Carsten ^b  

^a CHANGZHOU UNIVERSITY   (China)

^b RWTH AACHEN UNIVERSITY   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

EPOXIDE; FLUORINATED HYDROCARBON; SILVER; THIOL DERIVATIVE;

CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY;

CATALYSIS; EPOXY COMPOUNDS; HYDROCARBONS, FLUORINATED; MOLECULAR STRUCTURE; SILVER; SULFHYDRYL COMPOUNDS;

EID: 84934933041     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/acs.orglett.5b01537     Document Type: Article

References (71)

1. O'Hagan, D.; Rzepa, H. S. Chem. Commun. 1997, 645
2. Hagmann, W. K. J. Med. Chem. 2008, 51, 4359
3. Müller, K.; Faeh, C.; Diederich, F. Science 2007, 317, 1881
4. Purser, S.; Moore, P. R.; Swallow, S.; Gouverneur, V. Chem. Soc. Rev. 2008, 37, 320
5. Tomashenko, O. A.; Grushin, V. V. Chem. Rev. 2011, 111, 4475
6. Besset, T.; Schneider, C.; Cahard, D. Angew. Chem., Int. Ed. 2012, 51, 5048
7. Dmowski, W.; Kamiński, M. J. Fluorine Chem. 1983, 23, 207
8. Kuroboshi, M.; Hiyama, T. Tetrahedron Lett. 1992, 33, 4177
9. Markovskij, L. N.; Pashinnik, V. E.; Kirsanov, A. V. Synthesis 1973, 787
10. Klauke, E. Angew. Chem., Int. Ed. Engl. 1966, 5, 848
11. Abe, T.; Hayashi, E.; Baba, H.; Fukaya, H. J. Fluorine Chem. 1990, 48, 257
12. Pawelke, G. J. Fluorine Chem. 1991, 52, 229
13. Alonso, C.; de Marigorta, E. M.; Rubiales, G.; Palacios, F. Chem. Rev. 2015, 115, 1847
14. Barata-Vallejo, S.; Lantano, B.; Postigo, A. Chem.-Eur. J. 2014, 20, 16806
15. Zhu, W.; Wang, J.; Wang, S.; Gu, Z.; Acena, J. L.; Izawa, K.; Liu, H.; Soloshonok, V. A. J. Fluorine Chem. 2014, 167, 37
16. Yang, X.; Wu, T.; Phipps, R. J.; Toste, F. D. Chem. Rev. 2015, 115, 826
17. Charpentier, J.; Fruh, N.; Togni, A. Chem. Rev. 2015, 115, 650
18. Estibaliz, M.; Cristina, N. Chem. Soc. Rev. 2014, 43, 6598
19. Xu, X.-H.; Matsuzaki, K.; Shibata, N. Chem. Rev. 2015, 115, 731
20. Zhang, C. Adv. Synth. Catal. 2014, 356, 2895
21. Egami, H.; Sodeoka, M. Angew. Chem., Int. Ed. 2014, 53, 8294
22. Chu, L.; Qing, F.-L. Acc. Chem. Res. 2014, 47, 1513
23. Liu, X.; Xu, C.; Wang, M.; Liu, Q. Chem. Rev. 2015, 115, 683
24. Umemoto, T.; Adachi, K.; Ishihara, S. J. Org. Chem. 2007, 72, 6905
25. Niedermann, K.; Früh, N.; Vinogradova, E.; Wiehn, M. S.; Moreno, A.; Togni, A. Angew. Chem., Int. Ed. 2011, 50, 1059
26. For a computational study on such reagents, see: Sala, O.; Lüthi, H. P.; Togni, A.; Iannuzzi, M.; Hutter, J. J. Comput. Chem. 2015, 36, 785
27. Niedermann, K.; Früh, N.; Senn, R.; Czarniecki, B.; Verel, R.; Togni, A. Angew. Chem., Int. Ed. 2012, 51, 6511
28. For a recent overview on the trifluoromethanide anion, see: Santschi, N.; Gilmour, R. Angew. Chem., Int. Ed. 2014, 53, 11414
29. Johnson, C. R. Acc. Chem. Res. 1973, 6, 341
30. Reggelin, M.; Zur, C. Synthesis 2000, 1
31. Harmata, M. Chemtracts 2003, 16, 660
32. Gais, H.-J. Heteroatom Chem. 2007, 18, 472
33. Craig, D.; Grellepois, F.; White, A. J. P. J. Org. Chem. 2005, 70, 6827
34. Okamura, H.; Bolm, C. Chem. Lett. 2004, 33, 482
35. See also: Bizet, V.; Hendriks, C. M. M.; Bolm, C. Chem. Soc. Rev. 2015, 44, 3378
36. Yadav, M. R.; Rit, R. K.; Shankar, M.; Sahoo, A. K. J. Org. Chem. 2014, 79, 6123
37. Yadav, M. R.; Rit, R. K.; Sahoo, A. K. Chem.-Eur. J. 2012, 18, 5541
38. Yadav, M. R.; Rit, R. K.; Sahoo, A. K. Org. Lett. 2013, 15, 1638
39. Rit, R. K.; Yadav, M. R.; Sahoo, A. K. Org. Lett. 2014, 16, 968
40. Dong, W.; Wang, L.; Parthasarathy, K.; Pan, F.; Bolm, C. Angew. Chem., Int. Ed. 2013, 52, 11573
41. Parthasarathy, K.; Bolm, C. Chem.-Eur. J. 2014, 20, 4896
42. Dong, W.; Parthasarathy, K.; Cheng, Y.; Pan, F.; Bolm, C. Chem.-Eur. J. 2014, 20, 15732
43. Cheng, Y.; Bolm, C. Angew. Chem., Int. Ed. 2015, 10.1002/anie.201501583
44. Walker, D. P.; Zawistoski, M. P.; McGlynn, M. A.; Kung, D. W.; Bonnette, P. C.; Baumann, A.; Buckbinder, L.; Houser, J. A.; Boer, J.; Mistry, A.; Han, S.; Xing, L.; Guzman-Perez, A. Bioorg. Med. Chem. Lett. 2009, 19, 3253
45. Zhu, Y.; Loso, M. R.; Watson, G. B.; Sparks, T. C.; Rogers, R. B.; Huang, J. X.; Gerwick, B. C.; Babcock, J. M.; Kelley, D.; Hegde, V. B.; Nugent, B. M.; Renga, J. M.; Denholm, I.; Gorman, K.; DeBoer, G. J.; Hasler, J.; Meade, T.; Thomas, J. D. J. Agric. Food Chem. 2011, 59, 2950
46. Park, S. J.; Buschmann, H.; Bolm, C. Bioorg. Med. Chem. Lett. 2011, 21, 4888
47. Chen, X. Y.; Park, S. J.; Buschmann, H.; De Rosa, M.; Bolm, C. Bioorg. Med. Chem. Lett. 2012, 22, 4307
48. Sparks, T. C.; Watson, G. B.; Loso, M. R.; Geng, C.; Babcock, J. M.; Thomas, J. D. Pestic. Biochem. Physiol. 2013, 107, 1
49. Park, S. J.; Baars, H.; Mersmann, S.; Buschmann, H.; Baron, J. M.; Amann, P. M.; Czaja, K.; Hollert, H.; Bluhm, K.; Redelstein, R.; Bolm, C. ChemMedChem 2013, 8, 217
50. Lücking, U. Angew. Chem., Int. Ed. 2013, 52, 9399
51. Bizet, V.; Kowalczyk, R.; Bolm, C. Chem. Soc. Rev. 2014, 43, 2426
52. Shen, X.; Hu, J. Eur. J. Org. Chem. 2014, 4437
53. For N -trifluoromethylthiolations of sulfoximines, see: Bohnen, C.; Bolm, C. Org. Lett. 2015, 10.1021/acs.orglett.5b01384
54. The molecular structure of 2l was determined by X-ray crystallo-graphic analysis. CCDC 1056841 (2l) contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from the Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data-request/cif.
55. Liu, J.-F.; Xian, H.-D.; Li, H.-Q.; Zhao, G.-L. Z. Kristallogr.-New Cryst. Struct. 2009, 224, 69
56. Presti, L. L.; Orlando, A. M.; Loconte, L.; Destro, R.; Ortoleva, E.; Soave, R.; Gatti, C. Cryst. Growth Des. 2014, 14, 4418
57. Peter, M. K.; Luc, V. M. Acta Crystallogr. Sect. E: Struct. Rep. Online 2010, 66, 2353
58. Zhu, H.-Y.; Guo, Y.-N.; Yang, D.-S. Z. Kristallogr.-New Cryst. Struct. 2010, 225, 359
59. Ogden, P. H.; Mitsch, R. A. J. Am. Chem. Soc. 1967, 89, 5007 [bis(trifluoromethyl)carbodiimides such as F3CN=C=NCF3]
60. Abe, T.; Shreeve, J. Inorg. Chem. 1981, 20, 2894 [sulfilimines such as (F3C)2S=NCF(CF3)2]
61. For a general overview on the use of silver in organic chemistry, see: Silver in Organic Chemistry; Harmata, M., Ed.; John Wiley & Sons, Inc.: Hoboken, NJ, 2010.
62. Moore, W. M.; Codella, P. J. J. Phys. Chem. 1988, 92, 4421
63. Maji, A.; Hazra, A.; Maiti, D. Org. Lett. 2014, 16, 4524
64. Ye, Y.; Lee, S. H.; Sanford, M. S. Org. Lett. 2011, 13, 5464
65. Wu, X.; Chu, L.; Qing, F.-L. Angew. Chem., Int. Ed. 2013, 52, 2198
66. Wang, Y.-F.; Qiu, J.; Kong, D.; Chen, F.-X. Synlett 2014, 25, 1731
67. Wang, X.; Xu, Y.; Zhou, Y.; Zhang, Y.; Wang, J. Synthesis 2014, 46, 2143
68. Li, Z.; Wang, Z.; Zhu, L.; Tan, X.; Li, C. J. Am. Chem. Soc. 2014, 136, 16439
69. Zhao, H.; Fan, X.; Yu, J.; Zhu, C. J. Am. Chem. Soc. 2015, 137, 3490
70. Zhang, C.; Li, Z.; Zhu, L.; Yu, L.; Wang, Z.; Li, C. J. Am. Chem. Soc. 2013, 135, 14802
71. For a suggested reductive elimination of Ag(III) intermediates, see: Yang, M.; Su, B.; Wang, Y.; Chen, K.; Jiang, X.; Zhang, Y.-F.; Zhang, X.-S.; Chen, G.; Cheng, Y.; Cao, Z.; Guo, Q.-Y.; Wang, L.; Shi, Z.-J. Nat. Commun. 2014, 5, 4707.