Journal of the American Chemical Society
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D.; Dang, H.; Fu, F.; Prakash, G. K. S. J. Fluorine Chem. 2017, 203, 130. (g)
philic substitution of alkyl (pseudo)halides, cross-coupling with aryl
stannanes, and asymmetric difunctionalization of alkenes can also
be effectively accomplished by using TFBz reagent. We believe that
the ready availability of TFBz, the operational simplicity, as well as
the mildness of the reaction conditions will further intrigue wide
applications of TFBz in the synthesis of various trifluoromethox-
ylated molecules for different fields.
Zhang, Q. W.; Brusoe, A. T.; Mascitti, V.; Hesp, K. D.; Blakemore, D. C.;
Kohrt, J. T.; Hartwig, J. F. Angew. Chem., Int. Ed. 2016, 55, 9758. (h)
Chatalova-Sazepin, C.; Binayeva, M.; Epifanov, M.; Zhang, W.; Foth, P.;
Amador, C.; Jagdeo, M.; Boswell, B. R.; Sammis, G. M. Org. Lett. 2016, 18,
4570.
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(5) Selected examples: (a) Umemoto, T.; Adachi, K.; Ishihara, S. J. Org.
Chem. 2007, 72, 6905. (b) Koller, R.; Stanek, K.; Stolz, D.; Aardoom, R.;
Niedermann, K.; Togni, A. Angew. Chem. Int. Ed. 2009, 48, 4332. (c) Liang,
A.; Han, S.; Liu, Z.; Wang, L.; Li, J.; Zou, D.; Wu, Y.; Wu, Y. Chem.Eur. J.
2016, 22, 5102. (d) Liu, J.-B.; Chen, C.; Chu, L.; Chen, Z.-H.; Xu, X.-H.;
Qing, F.-L. Angew. Chem., Int. Ed. 2015, 54, 11839. (e) Fu, M.-L.; Liu, J.-B.;
Xu, X.-H.; Qing, F.-L. J. Org. Chem. 2017, 82, 3702. (f) Hojczyk, K. N.; Feng,
P.; Zhan, C.; Ngai, M.-Y. Angew. Chem., Int. Ed. 2014, 53, 14559.
(6) Selected examples on radical trifluoromethoxylation: (a) Venturini, F.
Navarrini, W.; Famulari, A.; Sansotera, M.; Dardani, P.; Tortelli, V. J.
Fluorine Chem. 2012, 140, 43. (b) Umemoto, T.; Zhou, M.; Hu, J.
CN201510431545.2, 2016. (c) Zheng, W.; Morales-Rivera, C. A.; Lee, J. W.;
Liu, P.; Ngai, M.-Y. Angew. Chem., Int. Ed. 2018, doi:
10.1002/anie.201800598.
ASSOCIATED CONTENT
Supporting Information
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Experimental procedures and characterization data. This material is
AUTHOR INFORMATION
Corresponding Author
(7) Selected examples using TFMT: (a) Noftle, R. E.; Cady, G. H. Inorg.
Chem. 1965, 4, 1010. (b) Taylor, S. L.; Martin, J. C. J. Org. Chem. 1987, 52,
4147. (c) Kolomeitsev, A. A.; Vorobyev, M.; Gillandt, H. Tetrahedron Lett.
2008, 49, 449. (d) Marrec, O.; Billard, T.; Vors, J.-P.; Pazenok, S.; Langlois,
B. R. J. Fluorine Chem. 2010, 131, 200. (e) Huang, C. H.; Liang, T.; Harada,
S.; Lee, E.; Ritter, T. J. Am. Chem. Soc. 2011, 133, 13308. (f) Chen, C.;
Chen, P.; Liu, G. J. Am. Chem. Soc. 2015, 137, 15648. (g) Chen, C.; Luo, Y.;
Fu, L.; Chen, P.; Lan, Y.; Liu, G. J. Am. Chem. Soc. 2018, 140, 1207. (h) Qi,
X.; Chen, P.; Liu, G. Angew. Chem., Int. Ed. 2017, 56, 9517. (i) Zha, G. F.;
Han, J. B.; Hu, X. Q.; Qin, H. L.; Fang, W. Y.; Zhang, C. P. Chem. Comm.
2016, 52, 7458. (j) Zhang, C.-P.; Vicic, D. A. Organometallics 2012, 31, 7812.
(k) Chen, S.; Huang, Y.; Fang, X.; Li, H.; Zhang, Z.; Hor, T. S.; Weng, Z.
Dalton Trans. 2015, 44, 19682.
(8) Selected examples using COF2: (a) Farnham, W. B.; Smart, B. E.;
Middleton, W. J.; Calabrese, J. C.; Dixon, D. A. J. Am. Chem. Soc. 1985, 107,
4565. (b) Trainor, G. L. J. Carbohydr. Chem. 1985, 4, 545. (c) Nishida, M.;
Vij, A.; Kirchmeier, R. L.; Shreeve, J. M. Inorg. Chem. 1995, 34, 6085.
(9) An example using DNTFB: Marrec, O.; Billard, T.; Vors, J.-P.; Pazenok,
S.; Langlois, B. R. Adv. Synth. Catal. 2010, 352, 2831.
(10) Examples using TFMS: (a) Guo, S.; Cong, F.; Guo, R.; Wang, L.; Tang,
P. Nat. Chem. 2017, 9, 546. (b) Jiang, X.; Deng, Z.; Tang, P. Angew. Chem.,
Int. Ed. 2018, 57, 292.
(11) Fiederling, N.; Haller, J.; Schramm, H. Org. Process Res. Dev. 2013, 17,
318.
(12) Flosser, D. A. Olofson, R. A. Tetrahedron Lett. 2002, 43, 4275
(13) Tadross, P. M.; Stoltz, B. M. Chem. Rev. 2012, 112, 3550.
(14) The trifluoromethylation-protonation of arynes has been describled
with only two examples, see Ref. 6c.
(15) Himeshima, Y.; Sonoda, T.; Kobayashi, H. Chem. Lett. 1983, 1211.
(16) (a) Zeng, Y.; Zhang, L.; Zhao, Y.; Ni, C.; Zhao, J.; Hu, J. J. Am. Chem.
Soc. 2013, 135, 2955. (b) Zeng, Y.; Hu, J. Chem.Eur. J. 2014, 20, 6866. (c)
Zeng, Y.; Hu, J. Org. Lett. 2016, 18, 856.
*E-mail: jinbohu@sioc.ac.cn
Notes
The authors declare no competing financial interests.
ACKNOWLEDGMENT
Financial support of this work by the National Basic Research Pro-
gram of China (2015CB931900, 2016YFB0101200), the National
Natural Science Foundation of China (21632009, 21421002,
21472221), the Key Program of the Chinese Academy of Sciences
(KGZD-EW-T08), the Key Research Program of Frontier Sciences
of CAS (QYZDJ-SSW-SLH049), the Shanghai Rising-Star Program
(16QA1404600), and the Youth Innovation Promotion Associa-
tion CAS (2014231) is gratefully acknowledged.
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