Abstract
Photoredox catalysis by well-known ruthenium(II) polypyridine complexes is a versatile tool for redox reactions in synthetic organic chemistry, because they can effectively catalyze single-electron-transfer (SET) processes by irradiation with visible light. These favorable properties of the catalysts provide a new strategy for efficient and selective radical reactions. Salts of tris(2,2′-bipyridine)ruthenium(II), [Ru(bpy)3]2+, were first reported in 1936. Since then, a number of works related to artificial photosynthesis and photofunctional materials have been reported, but only limited efforts had been devoted to synthetic organic chemistry. Remarkably, since 2008, this photocatalytic system has gained importance in redox reactions. In this chapter, we will present a concise review of seminal works on ruthenium photoredox catalysis around 2008, which will be followed by our recent research topics on trifluoromethylation of alkenes by photoredox catalysis.
Access this chapter
Tax calculation will be finalised at checkout
Purchases are for personal use only
References
Chatgilialoglu C, Studer A (eds) (2012) Encyclopedia of radical in chemistry, biology and materials. Wiley, Chichester
Juris A, Balzani V, Barigelletti F, Campagna S, Belser P, von Zelewsky A (1988) Ru(II) polypyridine complexes: photophysics, photochemistry, electrochemistry and chemluminescence. Coord Chem Rev 84:85–277
Roundhill DM (1994) Photochemistry and photophysics of metal complexes. Plenum, New York
Hedstrand DM, Kruizinga WH, Kellog RM (1978) Light induced and dye accelerated reductions of phenyl onium salts by 1,4-dihydropyridines. Tetrahedron Lett 19:1255–1258
Pac C, Ihama M, Yasuda M, Miyauchi Y, Sakurai H (1981) Ru(bpy)3 2+-mediated photoreduction of olefins with l-benzyl-1,4-dihydronicotinamide: a mechanistic probe for electron-transfer reactions of NAD(P)H-model compounds. J Am Chem Soc 103:6495–6497
Ishitani O, Pac C, Sakurai H (1984) Redox-photosensitized reactions. 11. Ru(bpy)3 2+-photosensitized reactions of 1-benzyl-1,4-dihydronicotinamide with aryl-substituted enones, derivatives of methyl cinnamate, and substituted cinnamonitriles: electron-transfer mechanism and structure-reactivity relationships. J Org Chem 49:26–34
Goren Z, Willner I (1983) Photochemical and chemical reduction of vicinal dibromides via phase transfer of 4,4′-bipyridinium radical: the role of radical disproportionation. J Am Chem Soc 105:7764–7765
Cano-Yelo H, Deronzier A (1984) Photocatalysis of the Pschorr reaction by tris-(2,2'-bipyridyl) ruthenium(II) in the phenanthrene series. J Chem Soc Perkin Trans 2:1093–1098
Hironaka K, Fukuzumi S, Tanaka T (1984) Tris(bipyridyl)ruthenium(II)-photosensitized reaction of 1-benzyl-1,4-dihydronicotinamide with benzyl bromide. J Chem Soc Perkin Trans 2:1705–1709
Mashraqui SH, Kellog RM (1985) 3-Methyl-2,3-dihydrobenzothiazoles as reducing agents. Dye enhanced photoreactions. Tetrahedron Lett 26:1453–1456
Tomioka H, Ueda K, Ohi H, Izawa Y (1986) Photochemical and chemical reduction of nitroalkenes using viologens as an electron phase-transfer catalyst. Chem Lett 1359–1362
Fukuzumi S, Mochizuki S, Tanaka T (1990) Photocatalytic reduction of phenacyl halides by 9,10-dihydro-10-methylacridine: control between the reductive and oxidative quenching pathways of tris(bipyridine)ruthenium complex utilizing an acid catalysis. J Phys Chem 94:722–726
Okada K, Okamoto K, Morita N, Okubo K, Oda M (1991) Photosensitized decarboxylative Michael addition through N-(acyloxy)phthalimides via an electron-transfer mechanism. J Am Chem Soc 113:9401–9402
Hamada T, Ishida H, Usui S, Watanabe Y, Tsumura K, Ohkubo K (1993) A novel photocatalytic asymmetric synthesis of (R)-(+)-1,1'-bi-2-naphthol derivatives by oxidative coupling of 3-substituted-2-naphthol with Δ-[Ru(menbpy)3]2+[menbpy = 4,4'-di(1R,2S,5R)-(-)-menthoxycarbonyl-2,2'-bipyridine], which posseses molecular helicity. J Chem Soc Chem Commun 909–911
Barton DHR, Csiba MA, Jaszberenyi JC (1994) Ru(bpy)3 2+-mediated addition of Se-phenyl p-tolueneselenosulfonate to electron rich olefins. Tetrahedron Lett 35:2869–2872
Zen JM, Liou SL, Kumar AS, Hsia MS (2003) An efficient and selective photocatalytic system for the oxidation of sulfides to sulfoxides. Angew Chem Int Ed 42:577–579
Hasegawa E, Takizawa S, Seida T, Yamaguchi A, Yamaguchi N, Chiba N, Takahashi T, Ikeda H, Akiyama K (2006) Photoinduced electron-transfer systems consisting of electron-donating pyrenes or anthracenes and benzimidazolines for reductive transformation of carbonyl compounds. Tetrahedron 62:6581–6588
Yoon TP, Ischay MA, Du J (2010) Visible light photocatalysis as a greener approach to photochemical synthesis. Nat Chem 2:527–532
Narayanam JMR, Stephenson CRJ (2011) Visible light photoredox catalysis: applications in organic synthesis. Chem Soc Rev 40:102–113
Teplý F (2011) Photoredox catalysis by [Ru(bpy)3]2+ to trigger transformations of organic molecules. Organic synthesis using visible-light photocatalysis and its 20th century roots. Collect Czech Chem Commun 76:859–917
Tucker JW, Stephenson CRJ (2012) Shining light on photoredox catalysis: theory and synthetic applications. J Org Chem 77:1617–1622
Xuan J, Xiao W-J (2012) Visible-light photoredox catalysis. Angew Chem Int Ed 51:6828–6838
Maity S, Zheng N (2012) A photo touch on amines: new synthetic adventures of nitrogen radical cations. Synlett 23:1851–1856
Shi L, Xia W (2012) Photoredox functionalization of C–H bonds adjacent to a nitrogen atom. Chem Soc Rev 41:7687–7697
Xi Y, Yi H, Lei A (2013) Synthetic applications of photoredox catalysis with visible light. Org Biomol Chem 11:2387–2403
Hari DP, König B (2013) The photocatalyzed Meerwein arylation: classic reaction of aryl diazonium salts in a new light. Angew Chem Int Ed 52:4734–4743
Prier CK, Rankic DA, MacMillan DWC (2013) Visible light photoredox catalysis with transition metal complexes: applications in organic synthesis. Chem Rev 113:5322–5363
Reckenthäler M, Griesbeck AG (2013) Photoredox catalysis for organic syntheses. Adv Synth Catal 355:2727–2744
Koike T, Akita M (2013) Visible-light-induced photoredox catalysis: an easy access to green radical chemistry. Synlett 24:2492–2505
Nicewicz DA, MacMillan DWC (2008) Merging photoredox catalysis with organocatalysis: the direct asymmetric alkylation of aldehydes. Science 322:77–80
Lelais G, MacMillan DWC (2006) Modern strategies in organic catalysis: the advent and development of iminium activation. Aldrichimica Acta 39:79–87
MacMillan DWC (2008) The advent and development of organocatalysis. Nature 455:304–308
Beeson TD, Mastracchio A, Hong J-B, Ashton K, MacMillan DWC (2007) Enantioselective organocatalysis using SOMO activation. Science 316:582–585
Nagib DA, Scott ME, MacMillan DWC (2009) Enantioselective α-trifluoromethylation of aldehydes via photoredox organocatalysis. J Am Chem Soc 131:10875–10877
Koike T, Akita M (2009) Photoinduced oxyamination of enamines and aldehydes with TEMPO catalyzed by [Ru(bpy)3]2+. Chem Lett 38:166–167
Yasu Y, Koike T, Akita M (2012) Sunlight-driven synthesis of γ-diketones via oxidative coupling of enamines with silyl enol ethers catalyzed by [Ru(bpy)3]2+. Chem Commun 48:5355–5357
Ischay MA, Anzovino ME, Du J, Yoon TP (2008) Efficient visible light photocatalysis of [2+2] enone cycloadditions. J Am Chem Soc 130:12886–12887
Crimmins MT (1988) Synthetic applications of intramolecular enone-olefin photocycloadditions. Chem Rev 88:1453–1473
Bach T (1998) Stereoselective intermolecular [2+2]-photocycloaddition reactions and their application in synthesis. Synthesis 683–708
Roh Y, Jang H-Y, Lynch V, Bauld NL, Krische MJ (2002) Anion radical chain cycloaddition of tethered enones: intramolecular cyclobutanation and Diels−Alder cycloaddition. Org Lett 4:611–613
Du J, Yoon TP (2009) Crossed intermolecular [2+2] cycloadditions of acyclic enones via visible light photocatalysis. J Am Chem Soc 131:14604–14605
Lu Z, Shen M, Yoon TP (2011) [3+2] Cycloadditions of aryl cyclopropyl ketone by visible light photocatalysis. J Am Chem Soc 133:1162–1164
Ischay MA, Lu Z, Yoon TP (2010) [2+2] Cycloadditions by oxidative visible light photocatalysis. J Am Chem Soc 132:8572–8574
Ischay MA, Ament MS, Yoon TP (2012) Crossed intermolecular [2 + 2] cycloaddtion of styrenes by visible light photocatalysis. Chem Sci 3:2807–2811
Narayanam JMR, Tucker JW, Stephenson CRJ (2009) Electron-transfer photoredox catalysis: development of a tin-free reductive dehalogenation reaction. J Am Chem Soc 131:8756–8757
Tucker JW, Nguyen JD, Narayanam JMR, Krabbe SW, Stephenson CRJ (2010) Tin-free radical cyclization reactions initiated by visible light photoredox catalysis. Chem Commun 46:4985–4987
Tucker JW, Narayanam JMR, Krabbe SW, Stephenson CRJ (2010) Electron transfer photoredox catalysis: intramolecular radical addition to indoles and pyrroles. Org Lett 12:368–371
Furst L, Matsuura BS, Narayanam JMR, Tucker JW, Stephenson CRJ (2010) Visible light-mediated intermolecular C-H functionalization of electron-rich heterocycles with malonates. Org Lett 12:3104–3107
Andrew RS, Becker JJ, Gagné MR (2010) Intermolecular addition of glycosyl halides to alkenes mediated by visible light. Angew Chem Int Ed 49:7274–7276
Condie AG, González-Gómez JC, Stephenson CRJ (2010) Visible-light photoredox catalysis: Aza-Henry reactions via C-H functionalization. J Am Chem Soc 132:1464–1465
Rueping M, Vila C, Koenigs RM, Poscharny K, Fabry DC (2011) Dual catalysis: combining photoredox and Lewis base catalysis for direct Mannich reactions. Chem Commun 47:2360–2362
Xuan J, Cheng Y, An J, Lu L-Q, Zhang X-X, Xiao W-J (2011) Visible light-induced intramolecular cyclization reactions of diamines: a new strategy to construct tetrahydroimidazoles. Chem Commun 47:8337–8339
Rueping M, Zhu S, Koenigs RM (2011) Photoredox catalyzed C–P bond forming reactions—visible light mediated oxidative phosphonylations of amines. Chem Commun 47:8679–8681
Zou Y-Q, Lu L-Q, Fu L, Chang N-J, Rong J, Chen J-R, Xiao W-J (2011) Visible-light-induced oxidation/[3+2] cycloaddition/oxidative aromatization sequence: a photocatalytic strategy to construct pyrrolo[2,1-a]isoquinolines. Angew Chem Int Ed 50:7171–7175
Freeman DB, Furst L, Condie AG, Stephenson CRJ (2012) Functionally diverse nucleophilic trapping of iminium intermediates generated utilizing visible light. Org Lett 14:94–97
Maity S, Zhu M, Shinabery RS, Zheng N (2012) Intermolecular [3+2] cycloaddition of cyclopropylamines with olefins by visible-light photocatalysis. Angew Chem Int Ed 51:222–226
Rueping M, Koenigs RM, Poscharny K, Fabry DC, Leonori D, Vila C (2012) Dual catalysis: combination of photocatalytic aerobic oxidation and metal catalyzed alkynylation reactions—C–C bond formation using visible light. Chem Eur J 18:5170–5174
Cai S, Zhao X, Wang X, Liu Q, Li Z, Wang DZ (2012) Visible-light-promoted C–C bond cleavage: photocatalytic generation of iminium ions and amino radicals. Angew Chem Int Ed 51:8050–8053
Zhao G, Yang C, Guo L, Sun H, Chen C, Xia W (2012) Visible light-induced oxidative coupling reaction: easy access to Mannich-type products. Chem Commun 48:2337–2339
DiRocco DA, Rovis T (2012) Catalytic asymmetric α-acylation of tertiary amines mediated by a dual catalysis mode: N-Heterocyclic carbene and photoredox catalysis. J Am Chem Soc 134:8094–8097
McNally A, Prier CK, MacMillan DWC (2011) Discovery of an α-amino C–H arylation reaction using the strategy of accelerated serendipity. Science 334:1114–1117
Kohls P, Jadhav D, Pandey G, Reiser O (2012) Visible light photoredox catalysis: generation and addition of N-aryltetrahydroisoquinoline-derived α-amino radicals to Michael acceptors. Org Lett 14:672–675
Miyake Y, Nakajima K, Nishibayashi Y (2012) Visible-light-mediated utilization of α-aminoalkyl radicals: addition to electron-deficient alkenes using photoredox catalysts. J Am Chem Soc 134:3338–3341
Ju X, Li D, Li W, Yu W, Bian F (2012) The reaction of tertiary anilines with maleimides under visible light redox catalysis. Adv Synth Catal 354:3561–3567
Zhu S, Das A, Bui L, Zhou H, Curran DP, Rueping M (2013) Oxygen switch in visible-light photoredox catalysis: radical additions and cyclizations and unexpected C−C-bond cleavage reactions. J Am Chem Soc 135:1823–1829
Hiyama T (2000) Organofluorine compounds: chemistry and applications. Springer, Berlin
Ojima I (ed) (2009) Fluorine in medicinal chemistry and chemical biology. Wiley, Oxford
Ma J-A, Cahard D (2004) Asymmetric fluorination, trifluoromethylation, and perfluoroalkylation reactions. Chem Rev 104:6119–6146
Shimizu M, Hiyama T (2005) Modern synthetic methods for fluorine-substituted target molecules. Angew Chem Int Ed 44:214–231
Ma J-A, Cahard D (2007) Strategies for nucleophilic, electrophilic, and radical trifluoromethylations. J Fluorine Chem 128:975–996
Tomashenko OA, Grushin VV (2011) Aromatic trifluoromethylation with metal complexes. Chem Rev 111:4475–4521
Furuya T, Kamlet AS, Ritter T (2011) Catalysis for fluorination and trifluoromethylation. Nature 473:470–477
Besset T, Schneider C, Cahard D (2012) Tamed arene and heteroarene trifluoromethylation. Angew Chem Int Ed 51:5048–5050
Studer A (2012) A “Renaissance” in radical trifluoromethylation. Angew Chem Int Ed 51:8950–8958
Hollingworth C, Gouverneur V (2012) Transition metal catalysis and nucleophilic fluorination. Chem Commun 48:2929–2942
Liu H, Gu Z, Jiang X (2013) Direct trifluoromethylation of the C–H bond. Adv Synth Catal 355:617–626
Liang T, Neumann CN, Ritter T (2013) Introduction of fluorine and fluorine-containing functional groups. Angew Chem Int Ed 52:8214–8264
Koike T, Akita M (2014) Trifluoromethylation by visible-light-driven photoredox catalysis. Top Catal. DOI: 10.1007/s11244-014-0259-7
Nagib DA, MacMillan DWC (2011) Trifluoromethylation of arenes and heteroarenes by means of photoredox catalysis. Nature 480:224–228
Nguyen JD, Tucker JW, Konieczynska MD, Stephenson CRJ (2011) Intermolecular atom transfer radical addition to olefins mediated by oxidative quenching of photoredox catalysts. J Am Chem Soc 133:4160–4163
Wallentin C-J, Nguyen JD, Finkbeiner P, Stephenson CRJ (2012) Visible light-mediated atom transfer radical addition via oxidative and reductive quenching of photocatalysts. J Am Chem Soc 134:8875–8884
Wilger DJ, Gesmundo NJ, Nicewicz DA (2013) Catalytic hydrotrifluoromethylation of styrenes and unactivated aliphatic alkenes via an organic photoredox system. Chem Sci 4:3160–3165
Iqbal N, Choi S, Ko E, Cho EJ (2012) Trifluoromethylation of heterocycles via visible light photoredox catalysis. Tetrahedron Lett 53:2005–2008
Iqbal N, Choi S, Kim E, Cho EJ (2012) Trifluoromethylation of alkenes by visible light photoredox catalysis. J Org Chem 77:11383–11387
Kim E, Choi S, Kim H, Cho EJ (2013) Generation of CF3-containing epoxides and aziridines by visible-light-driven trifluoromethylation of allylic alcohols and amines. Chem Eur J 19:6209–6212
Umemoto T (1996) Electrophilic perfluoroalkylating agents. Chem Rev 96:1757–1777
Eisenberger P, Gischig S, Togni A (2006) Novel 10-I-3 hypervalent iodine-based compounds for electrophilic trifluoromethylation. Chem Eur J 12:2579–2586
Kieltsch I, Eisenberger P, Togni A (2007) Mild electrophilic trifluoromethylation of carbon- and sulfur-centered nucleophiles by a hypervalent iodine(III)–CF3 reagent. Angew Chem Int Ed 46:754–757
Wolfe JP (2008) Stereoselective synthesis of saturated heterocycles via palladium-catalyzed alkene carboetherification and carboamination reactions. Synlett 2913–2937
Jensen KH, Sigman MS (2008) Mechanistic approaches to palladium-catalyzed alkene difunctionalization reactions. Org Biomol Chem 6:4083–4088
McDonald RI, Liu G, Stahl SS (2011) Palladium(II)-catalyzed alkene functionalization via nucleopalladation: stereochemical pathways and enantioselective catalytic applications. Chem Rev 111:2981–3019
Fuchikami T, Shibata Y, Urata H (1987) Transition-metal complex catalyzed polyfluoroalkylation. A facile synthesis of fluorine-containing oxiranes and enynes. Chem Lett 521–524
Kamigata N, Fukushima T, Yoshida M (1989) Reaction of trifluoromethanesulphonyl chloride with alkenes catalysed by a ruthenium(II) complex. J Chem Soc Chem Commun 1559–1560
Kamigata N, Fukushima T, Terakawa Y, Yoshida M, Sawada H (1991) Novel perfluoroalkylation of alkenes with perfluoroalkanesulphonyl chlorides catalysed by a ruthenium(II) complex. J Chem Soc Perkin Trans 1:627–633
Ignatowska J, Dmowski W (2007) Sodium dithionite initiated addition of CF2Br2, CF3I and (CF3)2CFI to allylaromatics synthesis and the reactivity of 4-aryl-1,1-difluorodienes and 4-aryl-1,1-bis(trifluoromethyl)dienes. J Fluorine Chem 128:997–1006
Mu X, Wu T, Wang H-Y, Guo Y-L, Liu G (2012) Palladium-catalyzed oxidative aryltrifluoromethylation of activated alkenes at room temperature. J Am Chem Soc 134:878–881
Janson PG, Ghoneim I, IIchenko NO, Szabó KJ (2012) Electrophilic trifluoromethylation by copper-catalyzed addition of CF3-transfer reagents to alkenes and alkynes. Org Lett 14:2882–2885
Zhu R, Buchwald SL (2012) Copper-catalyzed oxytrifluoromethylation of unactivated alkenes. J Am Chem Soc 134:12462–12465
Li Y, Studer A (2012) Transition-metal-free trifluoromethylaminoxylation of alkenes. Angew Chem Int Ed 51:8221–8224
Egami H, Shimizu R, Sodeoka M (2012) Oxytrifluoromethylation of multiple bonds using copper catalyst under mild conditions. Tetrahedron Lett 53:5503–5506
Feng C, Loh T-P (2012) Copper-catalyzed olefinic trifluoromethylation of enamides at room temperature. Chem Sci 3:3458–3462
Wu X, Chu L, Qing F-L (2013) Silver-catalyzed hydrotrifluoromethylation of unactivated alkenes with CF3SiMe3. Angew Chem Int Ed 52:2198–2202
Egami H, Shimizu R, Kawamura S, Sodeoka M (2013) Alkene trifluoromethylation coupled with C–C bond formation: construction of trifluoromethylated carbocycles and heterocycles. Angew Chem Int Ed 52:4000–4003
Egami H, Kawamura S, Miyazaki A, Sodeoka M (2013) Trifluoromethylation reactions for the synthesis of β-trifluoromethylamines. Angew Chem Int Ed 52:7841–7844
Mizuta S, Verhoog S, Engle KM, Khotavivattana T, O’Duill M, Wheelhouse K, Rassias G, Médebielle M, Gouverneur V (2011) Catalytic hydrotrifluoromethylation of unactivated alkenes. J Am Chem Soc 135:2505–2508
Nemeth G, Kapiller-Dezsofi R, Lax G, Simig G (1996) New practical synthesis of panomifene. The effect of 2-trifluoromethyl substituent on the stereoselectivity of dehydration of l, l,2-triarylethanols. Tetrahedron 52:12821–12830
Liu X, Shimizu M, Hiyama T (2004) A Facile stereocontrolled approach to CF3-substituted triarylethenes: synthesis of panomifene. Angew Chem Int Ed 43:879–882
Yasu Y, Koike T, Akita M (2012) Three-component oxytrifluoromethyation of alkenes: highly efficient and regioselective difunctionalization of C=C bonds mediated by photoreodx catalysts. Angew Chem Int Ed 51:9567–9571
Nie J, Guo H-C, Cahard D, Ma J-A (2011) Asymmetric construction of stereogenic carbon centers featuring a trifluoromethyl group from prochiral trifluoromethylated substrates. Chem Rev 111:455–529
Qiu X-L, Qing F-L (2011) Recent advances in the synthesis of fluorinated amino acids. Eur J Org Chem 3261–3278
Yasu Y, Koike T, Akita M (2013) Intermolecular aminotrifluoromethylation of alkenes by visible-light- driven photoreodx catalysis. Org Lett 15:2136–2139
Rivkin A, Chou T-C, Danishefsky SJ (2005) On the remarkable antitumor properties of fludelone: how we got there. Angew Chem Int Ed 44:2838–2850
Shimizu M, Takeda Y, Higashi M, Hiyama T (2009) 1,4-Bis(alkenyl)-2,5-dipiperidinobenzenes: minimal fluorophores exhibiting highly efficient emission in the solid state. Angew Chem Int Ed 48:3653–3656
Shimizu M, Takeda Y, Higashi M, Hiyama T (2011) Synthesis and photophysical properties of dimethoxybis(3,3,3-trifluoropropen-1-yl)benzenes: compact chromophores exhibiting violet fluorescence in the solid state. Chem Asian J 6:2536–2544
Shi Z, Davies J, Jang S-H, Kaminsky W, Jen AK-Y (2012) Aggregation induced emission (AIE) of trifluoromethyl substituted distyrylbenzenes. Chem Commun 48:7880–7882
Selby TP (1995) Preparation of substituted fused heterocyclic herbicides. PCT international patent application US5,389,600 (A)
Xu J, Luo D-F, Xiao B, Liu Z-J, Gong T-J, Fu Y, Liu L (2011) Copper-catalyzed trifluoromethylation of aryl boronic acids using a CF3 + reagent. Chem Commun 47:4300–4302
Liu T, Shen Q (2011) Copper-catalyzed trifluoromethylation of aryl and vinyl boronic acids with an electrophilic trifluoromethylating reagent. Org Lett 13:2342–2345
Parsons AT, Senecal TD, Buchwald SL (2012) Iron(II)-catalyzed trifluoromethylation of potassium vinyltrifluoroborates. Angew Chem Int Ed 51:2947–2950
He Z, Luo T, Hu M, Cao Y, Hu J (2012) Copper-catalyzed di- and trifluoromethylation of α, β-unsaturated carboxylic acids: a protocol for vinylic fluoroalkylations. Angew Chem Int Ed 51:3944–3947
Li Y, Wu L, Neumann H, Beller M (2013) Copper-catalyzed trifluoromethylation of aryl- and vinylboronic acids with generation of CF3-radicals. Chem Commun 49:2628–2630
Kim H, MacMillan DWC (2008) Enantioselective organo-SOMO catalysis: the α-vinylation of aldehydes. J Am Chem Soc 130:398–399
Yasu Y, Koike T, Akita M (2013) Visible-light-induced synthesis of a variety of trifluoromethylated alkenes from potassium vinyltrifluoroborates by photoredox catalysis. Chem Commun 49:2037–2039
Acknowledgment
This work was supported financially by Grants-in-Aid for Scientific Research from the Ministry of Education, Culture, Sports, Science of the Japanese Government (Nos. 23750174, 22350024, and 24108101).
Author information
Authors and Affiliations
Corresponding author
Editor information
Editors and Affiliations
Rights and permissions
Copyright information
© 2014 Springer-Verlag Berlin Heidelberg
About this chapter
Cite this chapter
Koike, T., Akita, M. (2014). Visible-Light-Induced Redox Reactions by Ruthenium Photoredox Catalyst. In: Dixneuf, P., Bruneau, C. (eds) Ruthenium in Catalysis. Topics in Organometallic Chemistry, vol 48. Springer, Cham. https://doi.org/10.1007/3418_2014_80
Download citation
DOI: https://doi.org/10.1007/3418_2014_80
Published:
Publisher Name: Springer, Cham
Print ISBN: 978-3-319-08481-7
Online ISBN: 978-3-319-08482-4
eBook Packages: Chemistry and Materials ScienceChemistry and Material Science (R0)