Organic Process Research & Development
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(10)
Senecal, T. D.; Parsons, A. T.; Buchwald, S. L. Room temperature aryl trifluoromethylation via copper-mediated oxidative
cross-coupling. J. Org. Chem. 2011, 76, 1174-1176.
(
11)
12)
Chu, L.; Qing, F. L. Copper-mediated oxidative trifluoromethylation of boronic acids. Org. Lett. 2010, 12, 5060-5063.
Chen, M.; Buchwald, S. L. Rapid and efficient trifluoromethylation of aromatic and heteroaromatic compounds using potassium
trifluoroacetate enabled by a flow system. Angew. Chem. Int. Ed. 2013, 52, 11628-11631.
(
(
13)
14)
Lefebvre, Q. Toward sustainable trifluoromethylation reactions: sodium triflinate under the spotlight. Synlett 2017, 28, 19-23.
Zhang, H.; Wang, H.; Luo, Y.; Chen, C.; Cao, Y.; Chen, P.; Guo, Y. L.; Lan, Y.; Liu, G. Regioselective palladium-catalyzed CH
bond trifluoroethylation of indoles: exploration and mechanistic insight. ACS Catal. 2018, 8, 2173-2180.
Abdiaj, I.; Bottecchia, C.; Alcazar, J.; Noёl, T. Visible-light-induced trifluoromethylation of highly functionalized arenes and
heteroarenes in continuous flow. Synthesis 2017, 49, 4978-4985.
(
0
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(15)
(16)
(17)
Sosa, V.; Melkie, M.; Sulca, C.; Li, J.; Tang, L.; Li, J.; Faris, J.; Foley, B.; Banh, T.; Kato, M.; Cheruzel, L. E. Selective light-
driven chemoenzymatic trifluoromethylation/hydroxylation of substituted arenes. ACS Catal. 2018, 8, 2225-2229.
Ye, Y.; Sanford, M. S. Merging visible-light photocatalysis and transition-metal catalysis in the copper-catalyzed
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trifluoromethylation of boronic acids with CF I. J. Am. Chem. Soc. 2012, 134, 9034-9037.
(18)
Das, Somnath.; Hashmi, A. S. K.; Schaub, T. Direct photoassisted α-trifluoromethylation of aromatic ketones with
trifluoroacetic anhydride (TFAA). Adv. Synth. Catal. 2019, 361, 720-724.
(19)
(20)
(21)
(22)
Beatty, J. W.; Douglas, J. J.; Cole, K. P.; Stephenson, C. R. J. A scalable and operationally simple radical trifluoromethylation.
Nat. Commun. 2015, 6, 7919-7924.
Yang, B.; Yu, D.; Xu, X. H.; Qing, F. L. Visible-light photoredox decarboxylation of perfluoroarene iodine (III) trifluoroacetates
for C-H trifluoromethylation of (hetero)arenes. ACS. Catal. 2018, 8, 2839-2846.
Beatty, J. W.; Douglas, J. J.; Miller, R.; Mc Atee, R. C.; Cole, K. P.; Stephenson, C. R.J. Photochemical perfluoroalkylation with
pyridine N-oxides: mechanistic insights and performance on a kilogram scale. Chem. 2016, 1, 456-472.
Iqbal, N.; Jung, J.; Park, S.; Cho, E. J. Controlled trifluoromethylation reactions of alkynes through visible‐light photoredox
catalysis. Angew. Chem. Int. Ed. 2014, 53, 539-542.
(23)
Straathof, N. J. W.; Cramer, S. E.; Hessel, V.; Noel, T. Practical photocatalytic trifluoromethylation and
hydrotrifluoromethylation of styrenes in batch and flow. Angew. Chem. 2016, 55, 15549-15553.
Le, C.; Chen, T. Q.; Liang, T.; Zhang, P.; MacMillan, D. W. C. Radical approach to the copper oxidative addition problem:
trifluoromethylation of bromoarenes. Science 2018, 360, 1010-1014.
(24)
(25)
(26)
(27)
Grinberg, V.; Vassiliev, Y. B. Investigation of the processes of electrochemical perfluoroalkylation and fluorosulphation: part 1.
electrode processes and the electrochemical perfluoroalkylation mechanism. J. Electroanal. Chem. 1992, 325, 167-184.
Lin, J.; Li, Z.; Kan, J.; Huang, S.; Su, W.; Li, Y. Photo-driven redox-neutral decarboxylative carbon-hydrogen
trifluoromethylation of (hetero) arenes with trifluoroacetic acid. Nat. Commun. 2017, 8, 14353-14359.
Sun, L.; Wei, G.; Song, Y.; Liu, Z.; Wang, L.; Li, Z. Soulotion-phase synthesis of Au@ZnO core-shell composites. Mater Lett.
2
006, 60, 1291-1295.
(28)
Silva, C. G.; Silva, C. G.; M. J.; Carabineiro, S. A.; Oliveira, J. W. L.; Baptista, D. L.; Bacsa, R.; Machado, B. F.; Serp, P.;
Figueiredo, J. L.; Silva, A. M. T.; Faria. J. L. Developing highly active photocatalysts: gold-loaded ZnO for solar phenol
oxidation. J. Catal. 2014, 316, 182-190.
(
29)
30)
Kim, K. J.; Kreider, P. B.; Chang, C. H.; Park, C. M.; Ahn, H. G. Visible light sensitive nanoscale Au–ZnO photocatalysts. J.
Nanopart. Res. 2013, 15, 1606-1616.
(
Sarina, S.; Waclawik, E. R.; Zhu, H. Photocatalysis on supported gold and silver nanoparticles under ultraviolet and visible light
irradiation. Green Chem. 2013, 15, 1814-1833.
(31)
Ye, W.; Long, R; Huang, H.; Xiong, Y. Plasmonic nanostructures in solar energy conversion. J. Mater. Chem. C. 2017, 5, 1008-
1
021.
(32)
Linic, S.; Christopher, P.; Ingram, D. B. Plasmonic-metal nanostructures for efficient conversion of solar to chemical energy.
Nat. Mater. 2011, 10, 911-921.
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