2.9 Fluorination Enabled by Photoredox Reactions

Abstract

In recent years, photoredox catalysis has become a useful strategy in the field of synthetic chemistry because generation of reactive radicals, ionic species, and organometallics under mild reaction conditions can be realized. This review mainly discusses fluorination reactions of carbon skeletons using photoredox catalysis. In addition, seminal works on photochemical hydrogen-atom transfer (HAT) and photocatalyst-free photoinduced electron-transfer systems are also handled. These systems can be applied to fluorination reactions of C—H bonds, C—C bonds, C=C bonds, and appropriate functional groups.

Key words

Photoredox catalysis - Metallaphotoredox catalysis - Hydrogen atom transfer (HAT) - Photoinduced electron transfer - Single electron transfer (SET) - Redox reaction - Radicals - Ionic radicals - Carbocationic species - Organometallics - SOMOphilic fluorination - Nucleophilic fluorination - C—H functionalization

• 1 Purser S, Moore PR, Swallow S, Gouverneur V. Chem. Soc. Rev. 2008; 37: 320

• 2 Wang J, Sánchez-Roselló M, Aceña JL, del Pozo C, Sorochinsky AE, Fustero S, Soloshonok VA, Liu H. Chem. Rev. 2014; 114: 2432

• 3 Zhou Y, Wang J, Gu Z, Wang S, Zhu W, Aceña JL, Soloshonok VA, Izawa K, Liu H. Chem. Rev. 2016; 116: 422

• 4 Mei H, Han J, Fustero S, Medio-Simon M, Sedgwick DM, Santi C, Ruzziconi R, Soloshonok VA. Chem.–Eur. J. 2019; 25: 11797

• 5 Ogawa Y, Tokunaga E, Kobayashi O, Hirai K, Shibata N. iScience 2020; 23: 101467

• 6 Hagmann WK. J. Med. Chem. 2008; 51: 4359

• 7 Fluorine in Medicinal Chemistry and Chemical Biology. Ojima I. Wiley-Blackwell; Chichester, UK 2009

• 8 Champagne PA, Desroches J, Hamel J.-D, Vandamme M, Paquin J.-F. Chem. Rev. 2015; 115: 9073

• 9 Lantano B, Postigo A. Org. Biomol. Chem. 2017; 15: 9954

• 10 Szpera R, Moseley DFJ, Smith LB, Sterling AJ, Gouverneur V. Angew. Chem. Int. Ed. 2019; 58: 14824

• 11 Yakubov S, Barham JP. Beilstein J. Org. Chem. 2020; 16: 2151

• 12 Visible Light Photocatalysis in Organic Chemistry. Stephenson CRJ, Yoon TP, MacMillan DWC. Wiley VCH; Weinheim (Germany) 2018

• 13 Romero NA, Nicewicz DA. Chem. Rev. 2016; 116: 10075

• 14 Matsui JK, Lang SB, Heitz DR, Molander GA. ACS Catal. 2017; 7: 2563

• 15 Marzo L, Pagire SK, Reiser O, König B. Angew. Chem. Int. Ed. 2018; 57: 10034

• 16 Protti S, Fagnoni M, Ravelli D. ChemCatChem 2015; 7: 1516

• 17 Capaldo L, Ravelli D. Eur. J. Org. Chem. 2017; 2056

• 18 Wencel-Delord J, Glorius F. Nature Chem. 2013; 5: 369

• 19 Cernak T, Dykstra KD, Tyagarajan S, Vachal P, Krska SW. Chem. Soc. Rev. 2016; 45: 546

• 20 Cannalire R, Pelliccia S, Sancineto L, Novellino E, Tron GC, Giustiniano M. Chem. Soc. Rev. 2021; 50: 766

• 21 Buckingham F, Gouverneur V. Chem. Sci. 2016; 7: 1645

• 22 Preshlock S, Tredwell M, Gouverneur V. Chem. Rev. 2016; 116: 719

• 23 Mella M, Fagnoni M, Freccero M, Fasani E, Albini A. Chem. Soc. Rev. 1998; 27: 81

• 24 Christl M, Braun M, Deeg O. Org. Biomol. Chem. 2013; 11: 2811

• 25 Albini A, Mella M, Freccero M. Tetrahedron 1994; 50: 575

• 26 Rueda-Becerril M, Sazepin CC, Leung JCT, Okbinoglu T, Kennepohl P, Paquin J.-F, Sammis GM. J. Am. Chem. Soc. 2012; 134: 4026

• 27 Bloom S, Knippel JL, Lectka T. Chem. Sci. 2014; 5: 1175

• 28 Bloom S, McCann M, Lectka T. Org. Lett. 2014; 16: 6338

• 29 Wang W.-D, Bakac A, Espenson JH. Inorg. Chem. 1995; 34: 6034

• 30 Waele VD, Poizat O, Fagnoni M, Bagno A, Ravelli D. ACS Catal. 2016; 6: 7174

• 31 Suzuki K, Mizuno N, Yamaguchi K. ACS Catal. 2018; 8: 10809

• 32 Xia J.-B, Zhu C, Chen C. J. Am. Chem. Soc. 2013; 135: 17494

• 33 Xia J.-B, Zhu C, Chen C. Chem. Commun. (Cambridge) 2014; 50: 11701

• 34 Halperin SD, Fan H, Chang S, Martin RE, Britton R. Angew. Chem. Int. Ed. 2014; 53: 4690

• 35 Halperin SD, Kwon D, Holmes M, Regalado EL, Campeau LC, DiRocco DA, Britton R. Org. Lett. 2015; 17: 5200

• 36 Nodwell MB, Bagai A, Halperin SD, Martin RE, Knust H, Britton R. Chem. Commun. (Cambridge) 2015; 51: 11783

• 37 West JG, Bedell TA, Sorensen EJ. Angew. Chem. Int. Ed. 2016; 55: 8923

• 38 Cantillo D, de Frutos O, Rincon JA, Mateos C, Kappe CO. J. Org. Chem. 2014; 79: 8486

• 39 Lee TC, Tong Y, Fu WC. Chem.–Asian J. 2023; 18 e202300723

• 40 Hu X.-Q, Chen J.-R, Xiao W.-J. Angew. Chem. Int. Ed. 2017; 56: 1960

• 41 Nobile E, Castanheiro T, Besset T. Angew. Chem. Int. Ed. 2021; 60: 12170

• 42 Dauncey EM, Morcillo SP, Douglas JJ, Sheikh NS, Leonori D. Angew. Chem. Int. Ed. 2018; 57: 744

• 43 Morcillo SP, Dauncey EM, Kim JH, Douglas JJ, Sheikh NS, Leonori D. Angew. Chem. Int. Ed. 2018; 57: 12945

• 44 Schneider TF, Kaschel J, Werz DB. Angew. Chem. Int. Ed. 2014; 53: 5504

• 45 Marek I, Masarwa A, Delaye PO, Leibeling M. Angew. Chem. Int. Ed. 2015; 54: 414

• 46 Komatsuda M, Yamaguchi J. Chem. Rec. 2023; 23 e202200281

• 47 Bloom S, Bume DD, Pitts CR, Lectka T. Chem.–Eur. J. 2015; 21: 8060

• 48 Pitts CR, Bloom MS, Bume DD, Zhang QA, Lectka T. Chem. Sci. 2015; 6: 5225

• 49 Pitts CR, Ling B, Snyder JA, Bragg AE, Lectka T. J. Am. Chem. Soc. 2016; 138: 6598

• 50 Wilger DJ, Grandjean JM, Lammert TR, Nicewicz DA. Nature Chem. 2014; 6: 720

• 51 Liu J, Rong J, Wood DP, Wang Y, Liang SH, Lin S. J. Am. Chem. Soc. 2024; 146: 4380

• 52 Shibutani S, Nagao K, Ohmiya H. J. Am. Chem. Soc. 2024; 146: 4375

• 53 Deng W, Feng W, Li Y, Bao H. Org. Lett. 2018; 20: 4245

• 54 Romero NA, Margrey KA, Tay NE, Nicewicz DA. Science (Washington, D. C.) 2015; 349: 1326

• 55 McManus JB, Nicewicz DA. J. Am. Chem. Soc. 2017; 139: 2880

• 56 Chen W, Huang Z, Tay NES, Giglio B, Wang M, Wang H, Wu Z, Nicewicz DA, Li Z. Science (Washington, D. C.) 2019; 364: 1170

• 57 Xuan J, Zhang Z.-G, Xiao W.-J. Angew. Chem. Int. Ed. 2015; 54: 15632

• 58 Jin Y, Fu H. Asian J. Org. Chem. 2017; 6: 368

• 59 Schwarz J, König B. Green Chem. 2018; 20: 323

• 60 Rueda-Becerril M, Mahé O, Drouin M, Majewski MB, West JG, Wolf MO, Sammis GM, Paquin J.-F. J. Am. Chem. Soc. 2014; 136: 2637

• 61 Ventre S, Petronijevic FR, MacMillan DWC. J. Am. Chem. Soc. 2015; 137: 5654

• 62 Péter Á, Perry GJP, Procter DJ. Adv. Synth. Catal. 2020; 362: 2135

• 63 Berger F, Plutschack MB, Riegger J, Yu W, Speicher S, Ho M, Frank N, Ritter T. Nature (London) 2019; 567: 223

• 64 Hopkinson MN, Sahoo B, Li J.-L, Glorius F. Chem.–Eur. J. 2014; 20: 3874

• 65 Singh PP, Singh PK, Srivastava V. Org. Chem. Front. 2023; 10: 216

• 66 Lang X, Zhao J, Chen X. Chem. Soc. Rev. 2016; 45: 3026

• 67 Skubi KL, Blum TR, Yoon TP. Chem. Rev. 2016; 116: 10035

• 68 Lipp A, Badir SO, Molander GA. Angew. Chem. Int. Ed. 2021; 60: 1714

• 69 Li J, Chen J, Sang R, Ham WS, Plutschack MB, Berger F, Chabbra S, Schnegg A, Genicot C, Ritter T. Nature Chem. 2020; 12: 56