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ChemComm
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DOI: 10.1039/C7CC02652H
COMMUNICATION
Journal Name
N. Neumann, G. B. Boursalian, T. Furuya, D. C. Choi, J. M.
Hooker and T. Ritter, Science, 2011, 334, 639; d) E. Lee, J. M.
Hooker and T. Ritter, J. Am. Chem. Soc. 2012, 134, 17456; e)
A. S. Kamlet, C. N. Neumann, E. Lee, S. M. Carlin, C. K.
Moseley, N. Stephenson, J. M. Hooker and T. Ritter, PLoS
Mukherjee, B. Maji, A. Tlahuext-Aca and F. Glorius, J. Am.
Chem. Soc., 2016, 138, 16200.
5
6
T. Khotavivattana, S. Verhoog, M. Tredwell, L. Pfeifer, S.
Calderwood, K. Wheelhouse, T. Lee Collier and V.
Gouverneur, Angew. Chem. Int. Ed., 2015, 54, 9991.
a) J. Zheng, L. Wang, J.-H. Lin, J.-C. Xiao and S. H. Liang,
Angew. Chem. Int. Ed., 2015, 54, 13236; b) J. Zheng, R.
Cheng, J.-H. Lin, D.-H. Yu, L. Ma, L. Jia, L. Zhang, L. Wang, J.-C.
Xiao and S. H. Liang, Angew. Chem. Int. Ed., 2017, 56, 3196.
P. Ivashkin, G. Lemonnier, J. Cousin, V. Grégoire, D. Labar, P.
Jubault and X. Pannecoucke, Chem. Eur. J., 2014, 20, 914.
A seminal report from Russel and Roques reported a single
example of the nucleophilic trifluoromethylation of 1,2-
diphenylsulfane, to generate the trifluoromethylthiolated
benzene under cold conditions, see: J. Russel and N. Roques,
Tetrahedron, 1998, 54, 13771.
ONE, 2013,
Taylor, S. Gruber, M. Huiban, J. Passchier, J. Mercier, C.
Génicot and V. Gouverneur, Angew. Chem. Int. Ed., 2014, 53
8, e59187; f) M. Tredwell, S. M. Preshlock, N. J.
,
7
6
751; g) M. G. Campbell and T. Ritter, Chem. Rev., 2015, 115,
12; h) K. J. Makaravage, A. F. Brooks, A. V. Mossine, M. S.
7
8
Sanford and P. J. H. Scott, Org. Lett., 2016, 18, 5440; i) A. V.
Mossine, A. F. Brooks, K. J. Makaravage, J. M. Miller, N.
Ichiishi and M. S. Sanford, Org. Lett., 2015, 17, 5780; j) S.
Preshlock, S. Calderwood, S. Verhoog, M. Tredwell, M.
Huiban, A. Hienzsch, S. Gruber, T. C. Wilson, N. J. Taylor, T.
Cailly, M. Schedler, T. Lee Collier, J. Passchier, R. Smits, J.
Millitor, A. Hoepping, M. Mueller, C. Genicot, J. Mercier and
V. Gouverneur, Chem. Commun., 2016, 52, 8361; k) F.
9
See the Supporting Information for detailed semi-automated
process.
Buckingham and V. Gouverneur, Chem. Sci., 2016, 7, 1645; l) 10 J. Aerts, S. Voccia, C. Lemaire, F. Giacomelli, D. Goblet, D.
X. Huang, W. Liu, H. Ren, R. Neelamegam, J. M. Hooker and J.
T. Groves, J. Am. Chem. Soc., 2014, 136, 6842; m) H. Shi, A.
Thonon, A. Pleneveaux, G. Warnock and A. Luxen,
Tetrahedron Lett., 2010, 51, 64.
Braun, L. Wang, S. H. Liang, N. Vasdev and T. Ritter, Angew. 11 Compound
Chem. Int. Ed., 2016, 55, 10786; n) C. N. Neumann, J. M. powder. See ref. 7
Hooker and T. Ritter, Nature, 2016, 534, 369. For recent 12 To carry out this study, 35 experiments of generation of
2 2
1 free of CH Cl can be obtained as a white
.
1
8
18
[
F]trifluoromethylation methodologies, see: a) S. Mizuta, I.
HCF
salt
2
F from (difluoromethyl)(mesityl)(phenyl) sulfonium
1 have been achieved leading to an average yield of 60%
S. R. Stenhagen, M. O’Duill, J. Wolstenhulme, A. K.
Kirjavainen, S. J. Forsback, M. Tredwell, G. Sandford, P. R.
Moore, M. Huiban, S. K. Luthra, J. Passchier, O. Solin and V.
Gouverneur, Org. Lett., 2013, 15, 2648; b) M. Huiban, M.
Tredwell, S. Mizuta, Z. Wan, X. Zhang, T. L. Collier and V.
proving the efficiency and the reproducibility of this
protocol. It should be also mentioned that all the
radiochemical yields reported in this study are calculated
1
8
from the radiochemical activity of HCF
2
F.
Gouverneur, Nat. Chem., 2013, 5, 941; c) T. Rühl, W. Rafique,
V. T. Lien and P. J. Riss, Chem. Commun., 2014, 50, 6056; d)
D. Van Der Born, J. D. M. Herscheid, R. V. A. Oru and D. J.
Vugts, Chem. Commun. 2013, 49, 4018.
4
For selected reviews, see: a) V. N. Boiko, Beilstein J. Org.
Chem., 2010, 6, 880; b) G. Landelle, A. Panossian, S. Pazenok,
J.-P. Vors and F. R. Leroux Beilstein J. Org. Chem., 2013,
9,
2
2
476; c) X.-H. Xu, K. Matsuzaki and N. Shibata, Chem. Rev.,
015, 115, 731; d) X. Shao, C. Xu, L. Lu and Q. Shen, Acc.
Chem. Res., 2015, 48, 1227; e) F. Toulgoat, S. Alazet and T.
Billard, Eur. J. Org. Chem., 2014, 2415; f) S. Barata-Vallejo, S.
Bonesi and A. Postigo, Org. Biomol. Chem., 2016, 14, 7150; g)
H. Zheng, Y. Huang and Z. Weng, Tetrahedron Lett., 2016, 57,
397; for selected examples, see: h) Q. Wang, F. Xie and X. Li,
1
J. Org. Chem., 2015, 80, 8361; i) Y. Huang, X. He, X. Lin, M.
Rong and Z. Weng, Org. Lett., 2014, 16, 3284; j) M. Hu, J.
Rong, W. Miao, C. Ni, Y. Han and J. Hu, Org. Lett., 2014, 16,
030; k) L. Zhu, G. Wang, Q. Guo, Z. Xu, D. Zhang and R.
2
Wang, Org. Lett., 2014, 16, 5390; l) J.-B. Liu, X.-H. Xu, Z.-H.
Chen and F.-L. Qing, Angew. Chem. Int. Ed., 2015, 54, 897; m)
T. Yang, L. Lu and Q. Shen, Chem. Commun., 2015, 51, 5479;
n) K.-Y Ye, X. Zhang, L.-X. Dai and S.-L. You, J. Org. Chem.,
2
014, 79, 12106; o) Z. Huang, Y.-D. Yang, E. Tokunaga and N.
Shibata, Org. Lett., 2015, 17, 1063; p) G. Danoun, B.
Bayarmagnai, M. F. Gruenberg and L. J. Goossen, Chem. Sci.,
2
014, 5, 1312; q) K. Zhang, J.-B. Liu and F.-L. Qing, Chem.
Commun., 2014, 50, 14157; r) W. Yin, Z. Wang and Y. Huang,
Adv. Synth. Catal., 2014, 356, 2998; s) Y. Yang, L. Xu, S. Yu, X.
Liu,Y. Zhang and D. A. Vicic, Chem. Eur. J. 2016, 22, 858; t) L.
Jiang, J. Qian, W. Yi, G. Lu, C. Cai and W. Zhang, Angew.
Chem. Int. Ed., 2015, 54, 14965; u) C. Chen, Y. Xie, L. Chu, R.-
W. Wang, X. Zhang and F.-L. Qing, Angew. Chem. Int. Ed.,
2
012, 51, 2492; v) Q. Glenadel, M. Bordy, S. Alazet, A. Tlili
and T. Billard, T. Asian J. Org. Chem., 2016, , 428; w) X. Liu,
R. An, X. Zhang, J. Luo and X. Zhao, Angew. Chem. Int. Ed.,
016, 55, 5846; x) X. Shao, X. Wang, T. Yang, L. Lu and Q.
Shen, Angew. Chem. Int. Ed., 2013, 52, 3457; y) S.
5
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