Excited radical anions and excited anions in visible light photoredox catalysis

References

[1] Konig B. Photocatalysis in organic synthesis - past, present, and future. Eur J Org Chem. 2017;1979–81.10.1002/ejoc.201700420Search in Google Scholar

[2] Prier CK, Rankic DA, MacMillan DW. Visible light photoredox catalysis with transition metal complexes: applications in organic synthesis. Chem Rev. 2013;113:5322–63.10.1021/cr300503rSearch in Google Scholar PubMed PubMed Central

[3] Schultz DM, Yoon TP. Solar synthesis: prospects in visible light photocatalysis. Science. 2014;343:985.10.1126/science.1239176Search in Google Scholar PubMed PubMed Central

[4] Yoon TP, Ischay MA, Du J. Visible light photocatalysis as a greener approach to photochemical synthesis. Nat Chem. 2010;2:527–32.10.1038/nchem.687Search in Google Scholar PubMed

[5] Ghosh I, Marzo L, Das A, Shaikh R, Konig B. Visible light mediated photoredox catalytic arylation reactions. Acc Chem Res. 2016;49:1566–77.10.1021/acs.accounts.6b00229Search in Google Scholar PubMed

[6] Romero NA, Nicewicz DA. Organic photoredox catalysis. Chem Rev. 2016;116:10075–166.10.1021/acs.chemrev.6b00057Search in Google Scholar PubMed

[7] Zeitler K. Photoredox catalysis with visible light. Angew Chem Int Ed. 2009;48:9785–9.10.1002/anie.200904056Search in Google Scholar PubMed

[8] Reiser O. Shining light on copper: unique opportunities for visible-light-catalyzed atom transfer radical addition reactions and related processes. Acc Chem Res. 2016;49:1990–6.10.1021/acs.accounts.6b00296Search in Google Scholar PubMed

[9] Ghosh I, Ghosh T, Bardagi JI, Konig B. Reduction of aryl halides by consecutive visible light-induced electron transfer processes. Science. 2014;346:725–8.10.1126/science.1258232Search in Google Scholar PubMed

[10] Gong HX, Cao Z, Li MH, Liao SH, Lin MJ. Photoexcited perylene diimide radical anions for the reduction of aryl halides: a bay-substituent effect. Org Chem Front. 2018;5:2296–302.10.1039/C8QO00445ESearch in Google Scholar

[11] Zeng L, Liu T, He C, Shi DY, Zhang FL, Duan CY. Organized aggregation makes insoluble perylene diimide efficient for the reduction of aryl halides via consecutive visible light-induced electron-transfer processes. J Am Chem Soc. 2016;138:3958–61.10.1021/jacs.5b12931Search in Google Scholar PubMed

[12] Shang JT, Tang HY, Ji HW, Ma WH, Chen CC, Zhao JC. Synthesis, characterization, and activity of a covalently anchored heterogeneous perylene diimide photocatalyst. Chin J Catal. 2017;38:2094–101.10.1016/S1872-2067(17)62960-7Search in Google Scholar

[13] Rosso C, Filippini G, Cozzi PG, Gualandi A, Prato M. Highly Performing Iodoperfluoroalkylation of Alkenes Triggered by the Photochemical Activity of Perylene Diimides. ChemPhotoChem. 2019;3:193–97.10.1002/cptc.201900018Search in Google Scholar

[14] Ghosh I, Konig B. Chromoselective photocatalysis: controlled bond activation through light-color regulation of redox potentials. Angew Chem Int Ed. 2016;55:7676–9.10.1002/anie.201602349Search in Google Scholar PubMed

[15] van de Linde S, Loschberger A, Klein T, Heidbreder M, Wolter S, Heilemann M, et al. Direct stochastic optical reconstruction microscopy with standard fluorescent probes. Nat Protoc. 2011;6:991–1009.10.1038/nprot.2011.336Search in Google Scholar PubMed

[16] van de Linde S, Krstic I, Prisner T, Doose S, Heilemann M, Sauer M. Photoinduced formation of reversible dye radicals and their impact on super-resolution imaging. Photochem Photobiol Sci. 2011;10:499–506.10.1039/C0PP00317DSearch in Google Scholar PubMed

[17] Marzo L, Ghosh I, Esteban F, Konig B.Metal-free photocatalyzed cross coupling of bromoheteroarenes with pyrroles. ACS Catal. 2016;6:6780–4.10.1021/acscatal.6b01452Search in Google Scholar

[18] Das A, Ghosh I, Konig B. Synthesis of pyrrolo 1,2-a quinolines and ullazines by visible light mediated one- and twofold annulation of N-arylpyrroles with arylalkynes Chem Commun. 2016;52:8695–8.10.1039/C6CC04366FSearch in Google Scholar

[19] Graml A, Ghosh I, Konig B. Synthesis of arylated nucleobases by visible light photoredox catalysis. J Org Chem. 2017;82:3552–60.10.1021/acs.joc.7b00088Search in Google Scholar PubMed

[20] Shaikh RS, Duesel SJ, Koenig B. Visible-light photo-arbuzov reaction of aryl bromides and trialkyl phosphites yielding aryl phosphonates. ACS Catal. 2016;6:8410–4.10.1021/acscatal.6b02591Search in Google Scholar

[21] Agrofoglio LA, Gillaizeau I, Saito Y. Palladium-assisted routes to nucleosides. Chem Rev. 2003;103:1875–916.10.1021/cr010374qSearch in Google Scholar PubMed

[22] Bardagi JI, Rossi RA. Short access to 6-substituted pyrimidine derivatives by the S(RN)1 mechanism. Synthesis of 6-substituted uracils through a one-pot procedure. J Org Chem. 2010;75:5271–7.10.1021/jo101064eSearch in Google Scholar

[23] Neumeier M, Sampedro D, Majek M, de la Pena O’Shea VA, Jacobi von Wangelin A, Perez-Ruiz R. Dichromatic photocatalytic substitutions of aryl halides with a small organic dye. Chem-Eur J. 2018;24:105–8.10.1002/chem.201705326Search in Google Scholar

[24] Bardagi JI, Ghosh I, Schmalzbauer M, Ghosh T, Konig B. Anthraquinones as photoredox catalysts for the reductive activation of aryl halides. Eur J Org Chem. 2018;34–40.10.1002/ejoc.201701461Search in Google Scholar

[25] Nelleborg P, Lund H, Eriksen J. Photochemical vs electrochemical electron-transfer reactions - one-electron reduction of aryl halides by photoexcited anion radicals Tetrahedron Lett. 1985;26:1773–6.10.1016/S0040-4039(00)98335-7Search in Google Scholar

[26] Eggins BR, Robertson PK. Photoelectrochemistry using quinone radical-anions. J Chem Soc Faraday Trans. 1994;90:2249–56.10.1039/ft9949002249Search in Google Scholar

[27] Schmalzbauer M, Ghosh I, Konig B. Utilising excited state organic anions for photoredox catalysis: activation of (hetero)aryl chlorides by visible light-absorbing 9-anthrolate anions. Faraday Discuss. 2019;215:364–78.10.1039/C8FD00176FSearch in Google Scholar PubMed

[28] Kerzig C, Goez M. Generating hydrated electrons through photoredox catalysis with 9-anthrolate. PCCP. 2015;17:13829–36.10.1039/C5CP01711DSearch in Google Scholar PubMed

[29] Kerzig C, Goez M. Combining energy and electron transfer in a supramolecular environment for the “green” generation and utilization of hydrated electrons through photoredox catalysis. Chem Sci. 2016;7:3862–8.10.1039/C5SC04800ASearch in Google Scholar PubMed PubMed Central

[30] Ghosh I, Shaikh RS, Konig B. Sensitization-initiated electron transfer for photoredox catalysis. Angew Chem Int Ed. 2017;56:8544–9.10.1002/anie.201703004Search in Google Scholar PubMed

[31] Ghosh I, Bardagi JI, Konig B. Photoredox catalysis: the need to elucidate the photochemical mechanism. Angew Chem Int Ed. 2017;56:12822–4.10.1002/anie.201707594Search in Google Scholar PubMed