7
7. For selected reviews about direct trifluoromethanesulfonylation of
18. (a) Figuly, G. D.; Martin, J. C. J. Org. Chem. 1980, 45, 3729–
3730;
ACCEPTED MANUSCRIPT
arenes, see: (a) Campbell, M. G.; Ritter, T. Org. Process Res. Dev.
2014, 18, 474−480;
(b) Neumann, C. N.; Ritter, T. Angew. Chem., Int. Ed. 2015, 54,
3216–3221;
(c) Preshlock, S.; Tredwell, M.; Gouverneur, V.; Chem. Rev. 2016,
116, 719−766;
(d) Yerien, D. E.; Bonesi, S.; Postigo, A. Org. Biomol. Chem.
2016, 14, 8398–8427.
(b) Wei, J.; Shen, Z.; Filatov, A. S.; Liu, Q.; Jordan, R. F.
Organometallics 2016, 35, 3557–3568.
19. (a) Linnert, M.; Bruhn, C.; Rüffer, T.; Schmidt, H.; Steinborn, D.
Organometallics 2004, 23, 3668–3673;
(b) Cabiddu, M. G.; Cabiddu, S.; Cadoni, E.; Cannas, R.; Fattuoni,
C.; Melis, S. Tetrahedron 1998, 54, 14095–14104.
20. (a) Gais, H.-J.; Vollhardt, J. Tetrahedron Lett. 1988, 29, 1529–
1532;
8. (a) Park, C. M.; Bruncko, M.; Adickes, J.; Bauch, J.; Ding, H.;
Kunzer, A.; Marsh, K. C.; Nimmer, P.; Shoemaker, A. R.; Song,
X.; Tahir, S. K.; Tse, C.; Wang, X.; Wendt, M. D.; Yang, X.;
Zhang, H.; Fesik, S. W.; Rosenberg, S. H.; Elmore, S. W. J. Med.
Chem. 2008, 51, 6902–6915;
(b) Lane, C.; Snieckus, V. Synlett 2000, 2000, 1294–1296;
(c) MacNeil, S. L.; Familoni, O. B.; Snieckus, V. J. Org. Chem.
2001, 66, 3662–3670.
21. (a) Katritzky, A. R.; Lue, P. J. Org. Chem. 1990, 55, 74–78;
(b) Peter, S.; Thomas, E. Synth. Commun. 2001, 31, 961–968;
(c) Schneider, C.; Broda, E.; Snieckus, V. Org. Lett. 2011, 13,
3588–3591.
(b) Brown, B. S.; Keddy, R.; Zheng, G. Z.; Schmidt, R. G.;
Koenig, J. R.; McDonald, H. A.; Bianchi, B. R.; Honore, P.; Jarvis,
M. F.; Surowy, C. S.; Polakowski, J. S.; Marsh, K. C.; Faltynek, C.
R.; Lee, C.-H. Bioorg. Med. Chem. 2008, 16, 8516–8525;
(c) Wang, G.; Zhang, H.; Zhou, J.; Ha, C.; Pei, D.; Ding, K.
Synthesis 2008, 2398–2404;
(d) Sleebs, B. E.; Czabotar, P. E.; Fairbrother, W. J.; Fairlie, W.
D.; Flygare, J. A.; Huang, D. C. S.; Kersten, W. J. A.; Koehler, M.
F. T.; Lessene, G.; Lowes, K.; Parisot, J. P.; Smith, B. J.; Smith,
M. L.; Souers, A. J.; Street, I. P.; Yang, H.; Baell, J. B. J. Med.
Chem. 2011, 54, 1914–1926;
(e) Ondachi, P.; Castro, A.; Luetje, C. W.; Damaj, M. I.;
Mascarella, S. W.; Navarro, H. A.; Carroll, F. I. J. Med. Chem.
2012, 55, 6512–6522;
(f) Hersperger, R. PCT Int. Appl. WO 9818796, 1998;
(g) Liu, X.; Zhang, Y.; Huang, W.; Tan, W.; Zhang, A. Bioorg.
Med. Chem. 2018, 26, 443–454.
22. (a) Snieckus, V.; Beaulieu, F.; Mohri, K.; Han, W.; Murphy, C.
K.; Davis, F. A. Tetrahedron Lett. 1994, 35, 3465–3468;
(b) Gaillard, S.; Papamicaël, C.; Dupas, G.; Marsais, F.; Levacher,
V. Tetrahedron 2005, 61, 8138–8147;
(c) Wessels, M.; Mahajan, V.; Boßhammer, S.; Raabe, G.; Gais,
H.-J. Eur. J. Org. Chem. 2011, 2431–2449.
23. Le, T.-N.; Diter, P.; Pégot, B.; Bournaud, C.; Toffano, M.; Guillot,
R.; Vo-Thanh, G.; Magnier, E. Org. Lett. 2016, 18, 5102−5105.
24. (a) Wittig, G.; Fuhrman, G. Ber. Dtsch. Chem. Ges. 1940, 73,
1197–1218;
(b) Wittig, G.; Pockels, U.; Dröge, H. Ber. Dtsch. Chem. Ges. A
1938, 71, 1903–1912.
25. Gilman, H.; Bebb, R. L. J. Am. Chem. Soc. 1939, 61, 109–112.
26. Zhong, W.; Liu, X. Tetrahedron Lett. 2014, 55, 4909–4911.
27. Cullen, S. C.; Shekhar, S.; Nere, N. K. J. Org. Chem. 2013, 78,
12194–12201.
9. (a) Droumaguet, C. L.; Mongin, O.; Werts, M. H. V.; Blanchard-
Desce, M. Chem. Commun. 2005, 2802–2804;
(b) Mongin, O.; PorrHs, L.; Charlot, M.; Katan, C.; Blanchard-
Desce, M. Chem. Eur. J. 2007, 13, 1481–1498;
(c) Rouxel, C.; Droumaguet, C. L.; Macé, Y.; Clift, S.; Mongin,
O.; Magnier, E.; Blanchard-Desce, M. Chem. Eur. J. 2012, 18,
12487–12497.
28. Park, C.-M.; Bruncko, M.; Adickes, J.; Bauch, J.; Ding, H.;
Kunzer, A.; Marsh, K. C.; Nimmer, P.; Shoemaker, A. R.; Song,
X.; Tahir, S. K.; Tse, C.; Wang, X.; Wendt, M. D.; Yang, X.;
Zhang, H.; Fesik, S. W.; Rosenberg, S. H.; Elmore, S. W. J. Med.
Chem. 2008, 51, 6902–6915.
10. (a) Wolff, J. J.; Gredel, F.; Oeser, T.; Irngartinger, H.; Pritzkow,
H. Chem. Eur. J. 1999, 5, 29–38;
29. Beaumont, J.; Clark, J. H. J. Fluorine Chem. 1991, 52, 295–300.
(b) Matsui, M.; Suzuki, M.; Hayashi, M.; Funabiki, K.; Ishigure,
Y.; Doke, Y.; Shiozaki, H. Bull. Chem. Soc. Jpn. 2003, 76, 607–
612;
(c) Hasegawa, A.; Naganawa, Y.; Fushimi, M.; Ishihara, K.;
Yamamoto, H. Org. Lett. 2006, 8, 3175–3178;
(d) Mouhtady, O.; Gaspard-Iloughmane, H.; Laporterie, A.; Roux,
C. L. Tetrahedron Lett. 2006, 47, 4125–4128;
(e) Kargbo, R.; Takahashi, Y.; Bhor, S.; Cook, G. R.; Lloyd-Jones,
G. C.; Shepperson, I. R. J. Am. Chem. Soc. 2007, 129, 3846–3847;
(f) Barta, K.; Franció, G.; Leitner, W.; Lloyd-Jones, G. C.;
Shepperson, I. R. Adv. Synth. Catal. 2008, 350, 2013–2023;
(g) Yanai, H.; Ogura, H.; Fukaya, H.; Kotani, A.; Kusu, F.;
Taguchi, T. Chem. Eur. J. 2011, 17, 11747–11751;
(h) Yanai, H.; Yoshino, T.; Fujita, M.; Fukaya, H.; Kotani, A.;
Kusu, F.; Taguchi, T. Angew. Chem., Int. Ed. 2013, 52, 1560–
1563; Angew. Chem. 2013, 125, 1600–1603.
11. (a) Sheppard, W. J. Am. Chem. Soc. 1963, 85, 1314–1318;
(b) Hansch, C.; Leo, A.; Taft, R. W. Chem. Rev. 1991, 91, 165–
195;
(c) Goumont, R.; Kizilian, E.; Buncel, E.; Terrier, F. Org. Biomol.
Chem. 2003, 1, 1741–1748;
(d) Terrier, F.; Magnier, E.; Kizilian, E.; Wakselman, C.; Buncel,
E. J. Am. Chem. Soc. 2005, 127, 5563–5571.
12. Nose, M.; Suzuki, H. Synthesis 2002, 8, 1065–1071.
13. Bilotta, J. A.; Chen, Z.; Chin, E.; Ding, Q.; Erickson, S. D.;
Gabriel, S. D.; Klumpp, K.; Ma, H.; Mertz, E.; Plancher, J.-M.;
Weikert, R. J. WO2014006066A1, 2014.
14. Boiko, V. N.; Gogoman, I. V.; Shchupak, G. M.; Yagupolskii, L.
M. Zh. Org. Khim. 1987, 23, 601–606.
15. Boiko, V. N.; Ignat'ev, N. V.; Yagupolskii, L. M. Zh. Org. Khim.
1981, 17, 1952–1958.
16. For reviews, see: (a) Snieckus, V. Chem. Rev. 1990, 90, 879–933;
(b) Schlosser, M. Angew. Chem. Int. Ed. 2005, 44, 376–393;
(c) D. Tilly, J. Magolan, J. Mortier, Chem. Eur. J. 2012, 18, 3804–
3820;
(d) G. A. El-Hiti, K. Smith, A. S. Hegazy, M. B. Alshammari, A.
M. Masmali, ARKIVOC 2015, iv, 19–47.
17. Figuly, G. D.; Loop, C. K.; Martin, J. C. J. Am. Chem. Soc. 1989,
111, 654–658.