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Direct C-H trifluoromethylation of di- and trisubstituted alkenes by photoredox catalysis

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Background: Trifluoromethylated alkene scaffolds are known as useful structural motifs in pharmaceuticals and agrochemicals as well as functional organic materials. But reported synthetic methods usually require multiple synthetic steps and/or exhibit limitation with respect to access to tri- and tetrasubstituted CF3-alkenes. Thus development of new methodologies for facile construction of Calkenyl-CF3 bonds is highly demanded. Results: The photoredox reaction of alkenes with 5-(trifluoromethyl) dibenzo[b,d]thiophenium tetrafluoroborate, Umemoto's reagent, as a CF 3 source in the presence of [Ru(bpy)3]2+ catalyst (bpy = 2,2'-bipyridine) under visible light irradiation without any additive afforded CF3-substituted alkenes via direct Calkenyl-H trifluoromethylation. 1,1-Di- and trisubstituted alkenes were applicable to this photocatalytic system, providing the corresponding multisubstituted CF 3-alkenes. In addition, use of an excess amount of the CF3 source induced double C-H trifluoromethylation to afford geminal bis(trifluoromethyl)alkenes. Conclusion: A range of multisubstituted CF 3-alkenes are easily accessible by photoredox-catalyzed direct C-H trifluoromethylation of alkenes under mild reaction conditions. In particular, trifluoromethylation of triphenylethene derivatives, from which synthetically valuable tetrasubstituted CF3-alkenes are obtained, have never been reported so far. Remarkably, the present facile and straightforward protocol is extended to double trifluoromethylation of alkenes. © 2014 Tomita et al; licensee Beilstein-Institut.




Tomita, R., Yasu, Y., Koike, T., & Akita, M. (2014). Direct C-H trifluoromethylation of di- and trisubstituted alkenes by photoredox catalysis. Beilstein Journal of Organic Chemistry, 10, 1099–1106.

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