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Scheuermann, J.  et al.: 2024 Science of Synthesis, 2023/5: DNA-Encoded Libraries DOI: 10.1055/sos-SD-241-00097
DNA-Encoded Libraries

2.6 On-DNA Photoredox-Catalyzed Reactions

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Book

Editors: Scheuermann, J. ; Li, Y. 

Authors: Barluenga, S. ; Bassi, G. ; Brunschweiger, A. ; Cai, B. ; Cazzamalli, S. ; Chheda, P. ; Cui, M. ; Cui, W. ; Fang, X. ; Farrera-Soler, L. ; Favalli, N. ; Feng, J.; Foley, T. L. ; Franzini, R. M. ; Georgiev, T. ; Gillingham, D. ; Gloger, A. ; Graham, J. D. ; Granados, A. ; Heiden, S.; Hou, W. ; Huang, Y. ; Keefe, A. D. ; Krusemark, C. J. ; Li, X. ; Li, Y. ; Lin, W. ; Litovchick, A.; Liu, G. ; Lu, X. ; Lucaroni, L. ; Ma, P. ; Migliorini, F. ; Molander, G. A. ; Neri, D. ; Nie, Q. ; Oehler, S. ; Prati, L. ; Puglioli, S. ; Reddavide, F. V. ; Satz, A. L. ; Sauter, B. ; Scheuermann, J. ; Schuman, D.; Simmons, N. ; Stanway-Gordon, H. A. ; Su, W. ; Sun, J. ; Thompson, M.; Vummidi, B. R.; Wang, X. ; Wang, Y. ; Wang, Z. ; Waring, M. J. ; Willems, S.; Winssinger, N. ; Xia, B. ; Xiong, F. ; Xu, H. ; Xu, L. ; Yang, G. ; Zhang, G. ; Zhang, Y. ; Zhou, Y. 

Title: DNA-Encoded Libraries

Print ISBN: 9783132455221; Online ISBN: 9783132437357; Book DOI: 10.1055/b000000342

1st edition © 2024. Thieme. All rights reserved.
Georg Thieme Verlag KG, Stuttgart

Subjects: Organic Chemistry

Science of Synthesis Reference Libraries



Parent publication

Title: Science of Synthesis

DOI: 10.1055/b-00000101

Series Editors: Fürstner, A. (Editor-in-Chief); Carreira, E. M.; Faul, M.; Kobayashi, S.; Koch, G.; Molander, G. A.; Nevado, C.; Trost, B. M.; You, S.-L.

Type: Multivolume Edition

Also available at
 


Abstract

The use of visible light as the driving force to trigger chemical transformations represents an attractive tool for organic synthesis, and it has been demonstrated to be an important and well-established strategy for accessing novel bond connections in a unique way via radical intermediates. This powerful synthetic tool is under continuous development and is finding ever-increasing applications in DNA-encoded library (DEL) synthesis. Since 2018, DEL chemists have new chemical space available thanks to the implementation of visible-light-mediated methods. This chapter details the state-of-the-art of on-DNA photoredox-catalyzed transformations Specifically, this review covers simple photoredox reactions, dual-catalytic metallaphotoredox reactions, and photoredox reactions initiated by electron donor/electron-acceptor (EDA) complexes.

Key words

DNA-encoded libraries - DNA-compatible reactions - visible-light - photocatalysis - cross-coupling reactions - metallaphotoredox - dual catalysis - EDA Complexes
 
  • 1 Patel S, Badir SO, Molander GA. Trends Chem. 2021; 3: 161
  • 2 Matsuo B, Granados A, Levitre G, Molander GA. Acc. Chem. Res. 2023; 56: 385
  • 3 Malone ML, Paegel BM. ACS Comb. Sci. 2016; 18: 182
  • 4 Jana R, Begam HM, Dinda R. Chem. Commun. (Cambridge) 2021; 57: 10842
  • 5 Ma F, Li J, Zhang S, Gu Y, Tan T, Chen W, Wang S, Xu H, Yang G, Lerner RA. ACS Catal. 2022; 12: 1639
  • 6 Lu X, Fan L, Phelps CB, Davie CP, Donahue CP. Bioconjugate Chem. 2017; 28: 1625
  • 7 Romero NA, Nicewicz DA. Chem. Rev. 2016; 116: 10075
  • 8 Barata-Vallejo S, Postigo A. Molecules 2019; 24: 4483
  • 9 Shaw MH, Twilton J, MacMillan DWC. J. Org. Chem. 2016; 81: 6898
  • 10 Science of Synthesis: Photocatalysis in Organic Synthesis. König B. Thieme; Stuttgart 2018
    Google Scholar
  • 11 Twilton J, Le CC, Zhang P, Shaw MH, Evans RW, MacMillan DWC. Nat. Rev. Chem. 2017; 1: 0052
  • 12 Brown DG, Boström J. J. Med. Chem. 2016; 59: 4443
  • 13 Matsui JK, Primer DN, Molander GA. Chem. Sci. 2017; 8: 3512
  • 14 Prier CK, Rankic DA, MacMillan DWC. Chem. Rev. 2013; 113: 5322
  • 15 Chen Y, Kamlet AS, Steinman JB, Liu DR. Nat. Chem. 2011; 3: 146
  • 16 Tellis JC, Primer DN, Molander GA. Science (Washington, D. C.) 2014; 345: 433
  • 17 Remeur C, Kelly CB, Patel NR, Molander GA. ACS Catal. 2017; 7: 6065
  • 18 Crisenza GEM, Mazzarella D, Melchiorre P. J. Am. Chem. Soc. 2020; 142: 5461
  • 19 Yang Z, Liu Y, Cao K, Zhang X, Jiang H, Li J. Beilstein J. Org. Chem. 2021; 17: 771
  • 20 Kölmel DK, Loach RP, Knauber T, Flanagan ME. ChemMedChem. 2018; 13: 2159
  • 21 Lovering F, Bikker J, Humblet C. J. Med. Chem. 2009; 52: 6752
  • 22 Giese B. Angew. Chem. Int. Ed. Engl. 1983; 22: 753
  • 23 Magueur G, Crousse B, Ourévitch M, Bonnet-Delpon D, Bégué J.-P. J. Fluorine Chem. 2006; 127: 637
  • 24 Lang SB, Wiles RJ, Kelly CB, Molander GA. Angew. Chem. Int. Ed. 2017; 56: 15073
  • 25 Gates KS, In: Reviews of Reactive Intermediate Chemistry Platz MS, Moss RA, Jones Jr M. Wiley-Interscience Hoboken, NJ 2007; 333-378
  • 26 Phelan JP, Lang SB, Sim J, Berritt S, Peat AJ, Billings K, Fan LJ, Molander GA. J. Am. Chem. Soc. 2019; 141: 3723
  • 27 Badir SO, Sim J, Billings K, Csakai A, Zhang X, Dong W, Molander GA. Org. Lett. 2020; 22: 1046
  • 28 Sarkar D, Bera N, Ghosh S. Eur. J. Org. Chem. 2019; 1310
  • 29 Kölmel DK, Ratnayake AS, Flanagan ME, Tsai M.-H, Duan C, Song C. Org. Lett. 2020; 22: 2908
  • 30 Wen H, Ge R, Qu Y, Sun J, Shi X, Cui W, Yan H, Zhang Q, An Y, Su W, Yang H, Kuai L, Satz AL, Peng X. Org. Lett. 2020; 22: 9484
  • 31 Shan J, Ling X, Liu J, Wang X, Lu X. Bioorg. Med. Chem. 2021; 42: 116234
  • 32 Jeffrey JL, Terrett JA, MacMillan DWC. Science (Washington, D. C.) 2015; 349: 1532
  • 33 Wu R, Du T, Sun W, Shaginian A, Gao S, Li J, Wan J, Liu G. Org. Lett. 2021; 23: 3486
  • 34 Shaw MH, Shurtleff VW, Terrett JA, Cuthbertson JD, MacMillan DWC. Science (Washington, D. C.) 2016; 352: 1304
  • 35 Lawrence DS, Copper JE, Smith CD. J. Med. Chem. 2001; 44: 594
  • 36 Zhang Y, Luo H, Ma H, Wan J, Ji Y, Shaginian A, Li J, Deng Y, Liu G. Bioconjugate Chem. 2021; 32: 1576
  • 37 Wu Y, Kim D, Teets TS. Synlett 2022; 33: 1154
  • 38 Nguyen JD, DʼAmato EM, Narayanam JM, Stephenson CRJ. Nat. Chem. 2012; 4: 854
  • 39 Badir SO, Lipp A, Krumb M, Cabrera-Afonso MJ, Kammer LM, Wu VE, Huang M, Csakai A, Marcaurelle LA, Molander GA. Chem. Sci. 2021; 12: 12036
  • 40 Ding H, Greenberg MM. J. Org. Chem. 2010; 75: 535
  • 41 Minisci F, Bernardi R, Bertini F, Galli R, Perchinummo M. Tetrahedron 1971; 27: 3575
  • 42 Krumb M, Kammer LM, Badir SO, Cabrera-Afonso MJ, Wu VE, Huang M, Csakai A, Marcaurelle LA, Molander GA. Chem. Sci. 2022; 13: 1023
  • 43 Shen Y, Yang G, Huang W, Shaginian A, Lin Q, Wan J, Li J, Deng Y, Liu G. Org. Lett. 2022; 24: 2650
  • 44 Yen-Pon E, Li L, Levitre G, Majhi J, McClain EJ, Voight EA, Crane EA, Molander GA. J. Am. Chem. Soc. 2022; 144: 12184
  • 45 Tellis JC, Kelly CB, Primer DN, Jouffroy M, Patel NR, Molander GA. Acc. Chem. Res. 2016; 49: 1429
  • 46 Kölmel DK, Meng J, Tsai M.-H, Que J, Loach RP, Knauber T, Wan J, Flanagan ME. ACS Comb. Sci. 2019; 21: 588
  • 47 Kölmel DK, Ratnayake AS, Flanagan ME. Biochem. Biophys. Res. Commun. 2020; 533: 201
  • 48 Ruff Y, Martinez R, Pellé X, Nimsgern P, Fille P, Ratnikov M, Berst F. ACS Comb. Sci. 2020; 22: 120
  • 49 Zuo Z, Ahneman DT, Chu L, Terrett JA, Doyle AG, MacMillan DWC. Science (Washington, D. C.) 2014; 345: 437
  • 50 Chowdhury R, Yu Z, Tong ML, Kohlhepp SV, Yin X, Mendoza A. J. Am. Chem. Soc. 2020; 142: 20143
  • 51 Lin B, Lu W, Chen Z.-y, Zhang Y, Duan Y.-z, Lu X, Yan M, Zhang X.-j. Org. Lett. 2021; 23: 7381
  • 52 Kolusu SRN, Nappi M. Chem. Sci. 2022; 13: 6982