An Unconventional Mechanistic Insight into SCF3 Formation from Difluorocarbene: Preparation of 18F-Labeled α-SCF3 Carbonyl Compounds

Angewandte Chemie - International Edition

Volumn 56, Issue 12, 2017, Pages 3196-3200

  Zheng, Jian ^a   Cheng, Ran ^b,c   Lin, Jin Hong ^a   Yu, Dong Hai ^a   Ma, Longle ^c   Jia, Lina ^d   Zhang, Lan ^d   Wang, Lu ^c   Xiao, Ji Chang ^a   Liang, Steven H ^c  

^a SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

^b TIANJIN UNIVERSITY   (China)

^c HARVARD MEDICAL SCHOOL   (United States)

^d SHANGHAI INSTITUTE OF APPLIED PHYSICS   (China)

Author keywords

18F labeling; difluorocarbene; fluorine; sulfuration; trifluoromethylthiolation

Indexed keywords

FLUORINE; FLUORINE COMPOUNDS; TRANSITION METALS;

CHEMICAL PROCESS; DIFLUOROCARBENE; ELEMENTAL SULFUR; SULFURATION; THIOCARBONYL; TRANSITION-METAL-MEDIATED; TRIFLUOROMETHYL; TRIFLUOROMETHYLTHIOLATION;

CARBONYL COMPOUNDS;

EID: 85013113424     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201611761     Document Type: Article

References (64)

1. D. L. S. Brahms, W. P. Dailey, Chem. Rev. 1996, 96, 1585–1632;
2. D. Burton, Z.-Y. Yang, W. Qiu, Chem. Rev. 1996, 96, 1641–1716;
3. W. R. Dolbier, M. A. Battiste, Chem. Rev. 2003, 103, 1071–1098;
4. C. Ni, J. Hu, Synthesis 2014, 46, 842–863; for recent examples, see:
5. K. Fuchibe, T. Aono, J. Hu, J. Ichikawa, Org. Lett. 2016, 18, 4502–4505;
6. Y. Zafrani, D. Amir, L. Yehezkel, M. Madmon, S. Saphier, N. Karton-Lifshin, E. Gershonov, J. Org. Chem. 2016, 81, 9180–9187;
7. P. Rullière, P. Cyr, A. B. Charette, Org. Lett. 2016, 18, 1988–1991;
8. H. Baars, J. Engel, L. Mertens, D. Meister, C. Bolm, Adv. Synth. Catal. 2016, 358, 2293–2299.
9. A. M. Trozzolo, E. Wasserman, W. A. Yager, J. Am. Chem. Soc. 1965, 87, 129–130.
10. J. Hu, C. Ni, Synthesis 2014, 46, 842–863;
11. J. Hu, W. Zhang, F. Wang, Chem. Commun. 2009, 7465–7478;
12. X.-Y. Deng, J.-H. Lin, J.-C. Xiao, Org. Lett. 2016, 18, 4384–4387.
13. D. J. Burton, D. M. Wiemers, J. Am. Chem. Soc. 1985, 107, 5014–5015;
14. D. M. Wiemers, D. J. Burton, J. Am. Chem. Soc. 1986, 108, 832–834;
15. J. H. Clark, M. A. McClinton, R. J. Blade, J. Chem. Soc. Chem. Commun. 1988, 638–639;
16. Q.-Y. Chen, S.-W. Wu, J. Chem. Soc. Chem. Commun. 1989, 705–706;
17. Q.-Y. Chen, J.-X. Duan, Tetrahedron Lett. 1993, 34, 4241–4244;
18. J.-X. Duan, D.-B. Su, Q.-Y. Chen, J. Fluorine Chem. 1993, 61, 279–284;
19. M. Huiban, M. Tredwell, S. Mizuta, Z. Wan, X. Zhang, T. L. Collier, V. Gouverneur, J. Passchier, Nat. Chem. 2013, 5, 941–944;
20. B. R. Ambler, R. A. Altman, Org. Lett. 2013, 15, 5578–5581;
21. X. Deng, J. Lin, J. Zheng, J. Xiao, Chin. J. Chem. 2014, 32, 689–693;
22. J. Zheng, J. H. Lin, X. Y. Deng, J. C. Xiao, Org. Lett. 2015, 17, 532–535;
23. Y. Liu, K. Zhang, Y. Huang, S. Pan, X.-Q. Liu, Y. Yang, Y. Jiang, X.-H. Xu, Chem. Commun. 2016, 52, 5969–5972.
24. J. Zheng, L. Wang, J. H. Lin, J. C. Xiao, S. H. Liang, Angew. Chem. Int. Ed. 2015, 54, 13236–13240;
25. Angew. Chem. 2015, 127, 13434–13438.
26. T. Khotavivattana, S. Verhoog, M. Tredwell, L. Pfeifer, S. Calderwood, K. Wheelhouse, T. L. Collier, V. Gouverneur, Angew. Chem. Int. Ed. 2015, 54, 9991–9995;
27. Angew. Chem. 2015, 127, 10129–10133.
28. J. Zheng, J. Cai, J.-H. Lin, Y. Guo, J.-C. Xiao, Chem. Commun. 2013, 49, 7513–7515;
29. J. Zheng, J.-H. Lin, J. Cai, J.-C. Xiao, Chem. Eur. J. 2013, 19, 15261–15266;
30. Q. Li, J.-H. Lin, Z.-Y. Deng, J. Zheng, J. Cai, J.-C. Xiao, J. Fluorine Chem. 2014, 163, 38–41;
31. X.-Y. Deng, J.-H. Lin, J. Zheng, J.-C. Xiao, Chem. Commun. 2015, 51, 8805–8808;
32. J. Zheng, J.-H. Lin, L.-Y. Yu, Y. Wei, X. Zheng, J.-C. Xiao, Org. Lett. 2015, 17, 6150–6153;
33. X.-Y. Deng, J.-H. Lin, J.-C. Xiao, J. Fluorine Chem. 2015, 179, 116–120;
34. X.-Y. Deng, J.-H. Lin, J.-C. Xiao, Org. Lett. 2016, 18, 4384–4387.
35. V. V. Levin, A. L. Trifonov, A. A. Zemtsov, M. I. Struchkova, D. E. Arkhipov, A. D. Dilman, Org. Lett. 2014, 16, 6256–6259;
36. Y. Qiao, T. Si, M.-H. Yang, R. A. Altman, J. Org. Chem. 2014, 79, 7122–7131;
37. L. I. Panferova, A. V. Tsymbal, V. V. Levin, M. I. Struchkova, A. D. Dilman, Org. Lett. 2016, 18, 996–999;
38. M.-Q. Hua, W. Wang, W.-H. Liu, T. Wang, Q. Zhang, Y. Huang, W.-H. Zhu, J. Fluorine Chem. 2016, 181, 22–29.
39. O. A. Tomashenko, V. V. Grushin, Chem. Rev. 2011, 111, 4475–4521.
40. C. Chen, L. Chu, F.-L. Qing, J. Am. Chem. Soc. 2012, 134, 12454–12457.
41. G. K. S. Prakash, F. Wang, Z. Zhang, R. Haiges, M. Rahm, K. O. Christe, T. Mathew, G. A. Olah, Angew. Chem. Int. Ed. 2014, 53, 11575–11578;
42. Angew. Chem. 2014, 126, 11759–11762.
43. Q.-Y. Chen, J.-X. Duan, J. Chem. Soc. Chem. Commun. 1993, 918–919.
44. H. Finch, L. M. Harwood, G. M. Robertson, R. C. Sewell, Tetrahedron Lett. 1989, 30, 2585–2588;
45. J. Huang, H.-J. Schanz, E. D. Stevens, S. P. Nolan, K. B. Capps, A. Bauer, C. D. Hoff, Inorg. Chem. 2000, 39, 1042–1045.
46. J. U. Köhler, J. Lewis, P. R. Raithby, Angew. Chem. Int. Ed. Engl. 1996, 35, 993–995;
47. Angew. Chem. 1996, 108, 1071–1073;
48. Z. Y. Zheng, J. Z. Chen, N. Luo, Z. K. Yu, X. W. Han, Organometallics 2006, 25, 5301–5310.
49. W. Mahler, Inorg. Chem. 1963, 2, 230.
50. W. J. Middleton, E. G. Howard, W. H. Sharkey, J. Am. Chem. Soc. 1961, 83, 2589–2590;
51. W. J. Middleton, E. G. Howard, W. H. Sharkey, J. Org. Chem. 1965, 30, 1375–1384;
52. M. Eschwey, W. Sundermeyer, D. S. Stephenson, Chem. Ber. 1983, 116, 1623–1630;
53. A. Waterfeld, Chem. Ber. 1990, 123, 1635–1640.
54. T. Furuya, A. S. Kamlet, T. Ritter, Nature 2011, 473, 470–477;
55. Y. Ye, M. S. Sanford, Synlett 2012, 23, 2005–2013;
56. P. Chen, G. Liu, Synthesis 2013, 45, 2919–2939;
57. H. Egami, M. Sodeoka, Angew. Chem. Int. Ed. 2014, 53, 8294–8308;
58. Angew. Chem. 2014, 126, 8434–8449;
59. C. Alonso, E. M. de Marigorta, G. Rubiales, F. Palacios, Chem. Rev. 2015, 115, 1847–1935.
60. Z. Weng, W. He, C. Chen, R. Lee, D. Tan, Z. Lai, D. Kong, Y. Yuan, K. W. Huang, Angew. Chem. Int. Ed. 2013, 52, 1548–1552;
61. Angew. Chem. 2013, 125, 1588–1592;
62. Z. Y. Wang, Q. Q. Tu, Z. Q. Weng, J. Organomet. Chem. 2014, 751, 830–834;
63. Y. Zhang, K. Gan, Z. Weng, Org. Process Res. Dev. 2016, 20, 799–802;
64. H. Zheng, Y. Huang, Z. Weng, Tetrahedron Lett. 2016, 57, 1397–1409.