[[(Ethoxycarbonyl)difluoromethyl]thio]phthalimide: A Shelf-Stable, Electrophilic Reagent with a Convertible Group for the Synthesis of Diversified Fluoroalkylthiolated Compounds

Organic Letters

Volumn 19, Issue 5, 2017, Pages 1032-1035

  Shen, Feng ^a   Zhang, Panpan ^a   Lu, Long ^a   Shen, Qilong ^a  

^a SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 85014691257     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/acs.orglett.7b00010     Document Type: Article

References (47)

1. Purser, S.; Moore, P. R.; Swallow, S.; Gouverneur, V. Chem. Soc. Rev. 2008, 37, 320 10.1039/B610213C
2. Landelle, G.; Panossian, A.; Leroux, F. R. Curr. Top. Med. Chem. 2014, 14, 941 10.2174/1568026614666140202210016
3. Manteau, B.; Pazenok, S.; Vors, J.-P.; Leroux, F. R. J. Fluorine Chem. 2010, 131, 140 10.1016/j.jfluchem.2009.09.009
4. Xu, X.-H.; Matsuzaki, K.; Shibata, N. Chem. Rev. 2015, 115, 731 10.1021/cr500193b
5. Ni, C.-F.; Hu, M.-Y.; Hu, J.-B. Chem. Rev. 2015, 115, 765 10.1021/cr5002386
6. Rico, I.; Wakselhan, C. Tetrahedron Lett. 1981, 22, 323 10.1016/0040-4039(81)80087-1
7. Fujita, T.; Iwasa, J.; Hansch, C. J. Am. Chem. Soc. 1964, 86, 5175 10.1021/ja01077a028
8. Landelle, G.; Panossian, A.; Leroux, F. R. Curr. Top. Med. Chem. 2014, 14, 941 10.2174/1568026614666140202210016
9. Boiko, V. N. Beilstein J. Org. Chem. 2010, 6, 880 10.3762/bjoc.6.88
10. He, W.-M.; Weng, Z.-Q. Prog. Chem. 2013, 25, 1071
11. Tlili, A.; Billard, T. Angew. Chem., Int. Ed. 2013, 52, 6818 10.1002/anie.201301438
12. Toulgoat, T.; Alazet, S.; Billard, T. Eur. J. Org. Chem. 2014, 2014, 2415 10.1002/ejoc.201301857
13. Shao, X.-X.; Xu, C.-F.; Lu, L.; Shen, Q. Acc. Chem. Res. 2015, 48, 1227 10.1021/acs.accounts.5b00047
14. Chachignon, H.; Cahard, D. Chin. J. Chem. 2016, 34, 445 10.1002/cjoc.201500890
15. Barata-Vallejo, S.; Bonesi, S.; Postigo, A. Org. Biomol. Chem. 2016, 14, 7150 10.1039/C6OB00763E
16. Munavalli, S.; Rohrbaugh, D. K.; Rossman, D. I.; Berg, F. J.; Wagner, G. W.; Durst, H. D. Synth. Commun. 2000, 30, 2847 10.1080/00397910008087435
17. Ferry, A.; Billard, T.; Langlois, B. R.; Bacqué, E. J. Org. Chem. 2008, 73, 9362 10.1021/jo8018544
18. Alazet, S.; Zimmer, L.; Billard, T. Chem.-Eur. J. 2014, 20, 8589 10.1002/chem.201403409
19. Yang, Y.-D.; Azuma, A.; Tokunaga, E.; Yamasaki, M.; Shiro, M.; Shibata, N. J. Am. Chem. Soc. 2013, 135, 8782 10.1021/ja402455f
20. Shao, X.-X.; Wang, X.-Q.; Yang, T.; Lu, L.; Shen, Q. Angew. Chem., Int. Ed. 2013, 52, 3457 10.1002/anie.201209817
21. Vinogradova, E. V.; Müller, P.; Buchwald, S. L. Angew. Chem., Int. Ed. 2014, 53, 3125 10.1002/anie.201310897
22. Xu, C.; Ma, B.; Shen, Q. Angew. Chem., Int. Ed. 2014, 53, 9316 10.1002/anie.201403983
23. Zhang, P.-P.; Li, M.; Xue, X.-S.; Xu, C.-F.; Zhao, Q.-C.; Liu, Y.-F.; Wang, H.-Y.; Guo, Y.-L.; Lu, L.; Shen, Q. J. Org. Chem. 2016, 81, 7486 10.1021/acs.joc.6b01178
24. Bu, M.-J.; Lu, G.-P.; Cai, C. Org. Chem. Front. 2016, 3, 630 10.1039/C6QO00020G
25. Brahms, D. L. S.; Dailey, W. P. Chem. Rev. 1996, 96, 1585 10.1021/cr941141k
26. Tozer, M. J.; Herpin, T. F. Tetrahedron 1996, 52, 8619 10.1016/0040-4020(96)00311-0
27. Hu, J.-B.; Zhang, W.; Wang, F. Chem. Commun. 2009, 7465 10.1039/b916463d
28. Xiong, H.-Y.; Pannecoucke, X.; Besset, T. Chem.-Eur. J. 2016, 22, 16734 10.1002/chem.201603438
29. Zhang, W.; Zhu, J.-M.; Hu, J.-B. Tetrahedron Lett. 2008, 49, 5006 10.1016/j.tetlet.2008.06.064
30. Wu, J.; Gu, Y.; Leng, X.-B.; Shen, Q. Angew. Chem., Int. Ed. 2015, 54, 7648 10.1002/anie.201502113
31. Wu, J.; Liu, Y.-F.; Lu, C.-H.; Shen, Q. Chem. Sci. 2016, 7, 3757 10.1039/C6SC00082G
32. Arimori, S.; Matsubara, O.; Takada, M.; Shiro, M.; Shibata, N. R. Soc. Open Sci. 2016, 3, 160102 10.1098/rsos.160102
33. Han, J.-B.; Qin, H.-L.; Ye, S.-H.; Zhu, L.; Zhang, C.-P. J. Org. Chem. 2016, 81, 2506 10.1021/acs.joc.6b00089
34. Lin, Y.-M.; Yi, W.-B.; Shen, W.-Z.; Lu, G.-P. Org. Lett. 2016, 18, 592 10.1021/acs.orglett.5b03654
35. Howard, J. L.; Schotten, C.; Alston, S. T.; Browne, D. L. Chem. Commun. 2016, 52, 8448 10.1039/C6CC02693A
36. Zhu, D.-H.; Shao, X.-X.; Hong, X.; Lu, L.; Shen, Q. Angew. Chem., Int. Ed. 2016, 55, 15807 10.1002/anie.201609468
37. Ismalaj, E.; Le Bars, D.; Billard, T. Angew. Chem., Int. Ed. 2016, 55, 4790 10.1002/anie.201601280
38. Xiong, H.-Y.; Bayle, A.; Pannecoucke, X.; Besset, T. Angew. Chem., Int. Ed. 2016, 55, 13490 10.1002/anie.201607231
39. Zibarev, A. V.; Miller, A. O.; Gatilov, Y. V.; Furin, G. G. Heteroat. Chem. 1990, 1, 443 10.1002/hc.520010604
40. Hutchinson, S. A.; Baker, S. P.; Linden, J.; Scammells, P. J. Bioorg. Med. Chem. 2004, 12, 4877 10.1016/j.bmc.2004.07.004
41. Eto, H.; Kaneko, Y.; Takeda, S.; Tokizawa, M.; Sato, S.; Yoshida, K.; Namiki, S.; Ogawa, M.; Maebshi, K.; Ishida, K.; Matsumoto, M.; Asaoka, T. Chem. Pharm. Bull. 2001, 49, 173 10.1248/cpb.49.173
42. Ma, B.-Q.; Shao, X.-X.; Shen, Q. J. Fluorine Chem. 2015, 171, 73 10.1016/j.jfluchem.2014.09.011
43. Honeker, R.; Ernst, J. B.; Glorius, F. Chem.-Eur. J. 2015, 21, 8047 10.1002/chem.201500957
44. Chen, F.; Hashmi, A. S. K. Org. Lett. 2016, 18, 2880 10.1021/acs.orglett.6b01188
45. Wan, W.; Ma, G.-B.; Li, J.-L.; Chen, Y.-R.; Hu, Q.-Y.; Li, M.-J.; Jiang, H.-Z.; Deng, H.-M.; Hao, J. Chem. Commun. 2016, 52, 1598 10.1039/C5CC09179A
46. Wang, Z.-T.; Zhu, L.; Yin, F.; Su, Z.-Q.; Li, Z.-D.; Li, C.-Z. J. Am. Chem. Soc. 2012, 134, 4258 10.1021/ja210361z
47. Kolb, H. C.; Finn, M. G.; Sharpless, K. B. Angew. Chem., Int. Ed. 2001, 40, 2004 10.1002/1521-3773(20010601)40:11<2004::AID-ANIE2004>3.0.CO;2-5