Organic Letters
Letter
W.; Gong, H. Org. Chem. Front. 2015, 2, 1411. (c) Knappke, C. E. I.;
Grupe, S.; Gartner, D.; Corpet, M.; Gosmini, C.; Jacobi von
Wangelin, A. Chem. - Eur. J. 2014, 20, 6828. (d) Weix, D. J. Acc.
Chem. Res. 2015, 48, 1767. (e) Moragas, T.; Correa, A.; Martin, R.
complex with Togni’s reagent may be the key to explaining the
trifluoromethyl transformation. However, considerable me-
chansitic studies are required to understand this novel catalytic
process.
́
́
Chem. - Eur. J. 2014, 20, 8242. (f) Nedelec, J. Y.; Perichon, J.;
Troupel, M. Top. Curr. Chem. 1997, 185, 141.
ASSOCIATED CONTENT
* Supporting Information
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(13) Only two examples using diboron as the reductant have been
reported for the coupling of two electrophiles: (a) Xu, H.; Zhao, C.;
Qian, Q.; Deng, W.; Gong, H. Chem. Sci. 2013, 4, 4022. (b) Lu, X.;
Wang, Y.; Zhang, B.; Pi, J.-J.; Wang, X.-X.; Gong, T.-J.; Xiao, B.; Fu, Y.
J. Am. Chem. Soc. 2017, 139, 12632.
(15) Tyrra, W.; Naumann, D.; Quadt, S.; Buslei, S.; Yagupolskii, Y.
L.; Kremlev, M. M. J. Fluorine Chem. 2007, 128, 813.
S
The Supporting Information is available free of charge on the
Detailed experimental procedures and characterization
(16) (a) Yang, C.-T.; Zhang, Z.-Q.; Tajuddin, H.; Wu, C.-C.; Liang,
J.; Liu, J.-H.; Fu, Y.; Czyzewska, M.; Steel, P. G.; Marder, T. B.; Liu, L.
Angew. Chem., Int. Ed. 2012, 51, 528. (b) Dudnik, A. S.; Fu, G. C. J.
Am. Chem. Soc. 2012, 134, 10693. (c) Ito, H.; Kubota, K. Org. Lett.
2012, 14, 890. (d) Yi, J.; Liu, J.-H.; Liang, J.; Dai, J.-J.; Yang, C.-T.;
Fu, Y.; Liu, L. Adv. Synth. Catal. 2012, 354, 1685. (e) Joshi-Pangu, A.;
Ma, X.; Diane, M.; Iqbal, S.; Kribs, R. J.; Huang, R.; Wang, C.-Y.;
Biscoe, M. R. J. Org. Chem. 2012, 77, 6629.
(17) Elimination of chloride from the Cu centers appears to be
crucial in a recent fluorination process: Liu, Z.; Chen, H.; Lv, Y.; Tan,
X.; Shen, H.; Yu, H.-Z.; Li, C. J. Am. Chem. Soc. 2018, 140, 6169.
(18) Le, C.; Chen, T. Q.; Liang, T.; Zhang, P.; MacMillan, D. W. C.
Science 2018, 360, 1010−1014.
(19) For an example of alkyl radical trapping with Cu intermediate,
see: Zhang, W.; Wang, F.; McCann, S. D.; Wang, D.; Chen, P.; Stahl,
S. S.; Liu, G. Science 2016, 353, 1014.
AUTHOR INFORMATION
Corresponding Authors
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ORCID
Notes
The authors declare no competing financial interest.
ACKNOWLEDGMENTS
Financial support was provided by the Chinese NSF (Nos.
21372151 and 21572127).
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REFERENCES
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