Reactivity and selectivity modulation within a molecular assembly: recent examples from photochemistry.
molecular assembly
organic synthesis
photochemistry
supramolecular
Journal
Photochemical & photobiological sciences : Official journal of the European Photochemistry Association and the European Society for Photobiology
ISSN: 1474-9092
Titre abrégé: Photochem Photobiol Sci
Pays: England
ID NLM: 101124451
Informations de publication
Date de publication:
May 2022
May 2022
Historique:
received:
01
10
2021
accepted:
17
11
2021
pubmed:
17
12
2021
medline:
10
6
2022
entrez:
16
12
2021
Statut:
ppublish
Résumé
In recent years, photochemical reactions have emerged as powerful transformations which significantly expand the repertoire of organic synthesis. However, a certain lack of selectivity can hamper their application and limit their scope. In this context, a major research effort continues to focus on an improved control over stereo- and chemoselectivity that can be achieved in molecular assemblies between photosubstrates and an appropriate host molecule. In this tutorial review, some recent, representative examples of photochemical reactions have been collected whose unique outcome is dictated by the formation of a molecular assembly driven by non-covalent weak interactions.
Identifiants
pubmed: 34914081
doi: 10.1007/s43630-021-00146-3
pii: 10.1007/s43630-021-00146-3
pmc: PMC9174329
doi:
Substances chimiques
Macromolecular Substances
0
Types de publication
Journal Article
Review
Langues
eng
Sous-ensembles de citation
IM
Pagination
719-737Subventions
Organisme : Deutsche Forschungsgemeinschaft
ID : TRR 325
Organisme : Deutsche Forschungsgemeinschaft
ID : Ba1372/24
Organisme : Deutsche Forschungsgemeinschaft
ID : Ba1372/23
Organisme : Deutsche Forschungsgemeinschaft
ID : Ba1372/20
Organisme : H2020 European Research Council
ID : 665951
Organisme : Schweizerischer Nationalfonds zur Förderung der Wissenschaftlichen Forschung
ID : P2EZP2 187999
Informations de copyright
© 2021. The Author(s).
Références
Roth, H. D. (1989). The beginnings of organic photochemistry. Angewandte Chemie International Edition, 28, 1193–1207. https://doi.org/10.1002/anie.198911931
doi: 10.1002/anie.198911931
Beeler, A. B. (2016). Introduction: photochemistry in organic synthesis. Chemical Reviews, 116(17), 9629–9630. https://doi.org/10.1021/acs.chemrev.6b00378
doi: 10.1021/acs.chemrev.6b00378
pubmed: 27625298
Morimoto, M., Bierschenk, S. M., Xia, K. T., Bergman, R. G., Raymond, K. N., & Toste, F. D. (2020). Advances in supramolecular host-mediated reactivity. Nature Catalysis, 3, 969–984. https://doi.org/10.1038/s41929-020-00528-3
doi: 10.1038/s41929-020-00528-3
Proctor, R. S. J., Colgan, A. C., & Phipps, R. J. (2020). Exploiting attractive non-covalent interactions for the enantioselective catalysis of reactions involving radical intermediates. Nature Chemistry, 12, 990–1004. https://doi.org/10.1038/s41557-020-00561-6
doi: 10.1038/s41557-020-00561-6
pubmed: 33077927
Rao, M., Wu, W., & Yang, C. (2021). Recent progress on the enantioselective excited-state photoreactions by pre-arrangement of photosubstrate(s). Green Synthesis and Catalysis, 2, 131–144. https://doi.org/10.1016/j.gresc.2021.03.005
doi: 10.1016/j.gresc.2021.03.005
Olivo, G., Capocasa, G., Del Giudice, D., Lanzalunga, O., & Di Stefano, S. (2021). New horizons for catalysis disclosed by supramolecular chemistry. Chemical Society Reviews, 50, 7681–7724. https://doi.org/10.1039/D1CS00175B
doi: 10.1039/D1CS00175B
pubmed: 34008654
Bibal, B., Mongin, C., & Bassani, D. M. (2014). Template effects and supramolecular control of photoreactions in solution. Chemical Society Reviews, 43, 4179–4198. https://doi.org/10.1039/C3CS60366K
doi: 10.1039/C3CS60366K
pubmed: 24480895
Ramamurthy, V., & Mondal, B. (2015). Supramolecular photochemistry concepts highlighted with select examples. Journal of Photochemistry and Photobiology C: Photochemistry Reviews, 23, 68–102. https://doi.org/10.1016/j.jphotochemrev.2015.04.002
doi: 10.1016/j.jphotochemrev.2015.04.002
Bhattacharyya, A., Sarkar, S. D., & Das, A. (2021). Supramolecular engineering and self-assembly strategies in photoredox catalysis. ACS Catalysis, 11, 710–733. https://doi.org/10.1021/acscatal.0c04952
doi: 10.1021/acscatal.0c04952
Hu, A., Guo, J. J., Pan, H., & Zuo, Z. (2018). Selective functionalization of methane, ethane, and higher alkanes by cerium photocatalysis. Science, 361(6403), 668–672. https://doi.org/10.1126/science.aat9750
doi: 10.1126/science.aat9750
pubmed: 30049785
Hu, A., Chen, Y., Guo, J. J., Yu, N., An, Q., & Zuo, Z. (2018). Cerium-catalyzed formal cycloaddition of cycloalkanols with alkenes through dual photoexcitation. Journal of the American Chemical Society, 140(42), 13580–13585. https://doi.org/10.1021/jacs.8b08781
doi: 10.1021/jacs.8b08781
pubmed: 30289250
Roberts, B. P. (1999). Polarity-reversal catalysis of hydrogen-atom abstraction reactions: Concepts and applications in organic chemistry. Chemical Society Reviews, 28, 25–35.
doi: 10.1039/a804291h
For a recent reviews on photoredox reactions employing Ni, see: Zhu, C., Yue, H., Chu, L., & Rueping, M. (2020) Recent advances in photoredox and nickel dual-catalyzed cascade reactions: pushing the boundaries of complexity. Chemical Science 11, 4051–4064. https://doi.org/10.1039/D0SC00712A
Welin, E. R., Le, C., Arias-Rotondo, D. M., McCusker, J. K., & MacMillan, D. W. C. (2017). Photosensitized, energy transfer-mediated organometallic catalysis through electronically excited nickel (II). Science, 355(6323), 380–385. https://doi.org/10.1126/science.aal2490
doi: 10.1126/science.aal2490
pubmed: 28126814
pmcid: 5664923
Heitz, D. R., Tellis, J. C., & Molander, G. A. (2016). Photochemical nickel-catalyzed C-H arylation: synthetic scope and mechanistic investigations. Journal of the American Chemical Society, 138(39), 12715–12718. https://doi.org/10.1021/jacs.6b04789
doi: 10.1021/jacs.6b04789
pubmed: 27653500
pmcid: 5054938
Shields, B. J., & Doyle, A. G. (2016). Direct C (sp
doi: 10.1021/jacs.6b08397
pubmed: 27653738
pmcid: 5215658
Lipp, A., Badir, S. O., & Molander, G. A. (2021). Stereoinduction in metallaphotoredox catalysis. Angewandte Chemie International Edition, 60, 1714–1726. https://doi.org/10.1002/anie.202007668
doi: 10.1002/anie.202007668
pubmed: 32677341
Kainz, Q. M., Matier, C. D., Bartoszewicz, A., Zultanski, S. L., Peters, J. C., & Fu, G. C. (2016). Asymmetric copper-catalyzed C-N cross-couplings induced by visible light. Science, 351(6274), 681–684. https://doi.org/10.1126/science.aad8313
doi: 10.1126/science.aad8313
pubmed: 26912852
pmcid: 4770572
Tanabe, J., Taura, D., Ousaka, N., & Yashima, E. (2017). Chiral template-directed regio-, diastereo-, and enantioselective photodimerization of an anthracene derivative assisted by complementary amidinium-carboxylate salt bridge formation. Journal of the American Chemical Society, 139(21), 7388–7398. https://doi.org/10.1021/jacs.7b03317
doi: 10.1021/jacs.7b03317
pubmed: 28485968
Waiskopf, N., Magdassi, S., & Banin, U. (2021). Quantum photoinitiators: toward emerging photocuring applications. Journal of the American Chemical Society, 143(2), 577–587. https://doi.org/10.1021/jacs.0c10554
doi: 10.1021/jacs.0c10554
pubmed: 33353293
Jiang, Y., Wang, C., Rogers, C. R., Kodaimati, M. S., & Weiss, E. A. (2019). Regio- and diastereoselective intermolecular [2+2] cycloadditions photocatalysed by quantum dots. Nature Chemistry, 11, 1034–1040. https://doi.org/10.1038/s41557-019-0344-4
doi: 10.1038/s41557-019-0344-4
pubmed: 31654049
pmcid: 6820707
Rono, L. J., Yayla, H. G., Wang, D. Y., Armstrong, M. F., & Knowles, R. R. (2013). Enantioselective photoredox catalysis enabled by proton-coupled electron transfer: development of an asymmetric aza-pinacol cyclization. Journal of the American Chemical Society, 135(47), 17735–17738. https://doi.org/10.1021/ja4100595
doi: 10.1021/ja4100595
pubmed: 24215561
Proctor, R. S. J., Davis, H. J., & Phipps, R. J. (2018). Catalytic enantioselective Minisci-type addition to heteroarenes. Science, 360(6387), 419–422. https://doi.org/10.1126/science.aar6376
doi: 10.1126/science.aar6376
pubmed: 29622723
Poplata, S., Bauer, A., Storch, G., & Bach, T. (2019). Intramolecular [2+2] photocycloaddition of cyclic enones: selectivity control by lewis acids and mechanistic implications. Chemistry A European Journal, 25, 8135–8148. https://doi.org/10.1002/chem.201901304
doi: 10.1002/chem.201901304
pubmed: 30983074
Brimioulle, R., & Bach, T. (2013). Enantioselective Lewis Acid Catalysis of Intramolecular Enone [2+2] Photocycloaddition reactions. Science, 342(6260), 840–843. https://doi.org/10.1126/science.1244809
doi: 10.1126/science.1244809
pubmed: 24233720
Poplata, S., & Bach, T. (2018). Enantioselective intermolecular [2+2] photocycloaddition reaction of cyclic enones and its application in a synthesis of (−)-grandisol. Journal of the American Chemical Society, 140(9), 3228–3231. https://doi.org/10.1021/jacs.8b01011
doi: 10.1021/jacs.8b01011
pubmed: 29458250
pmcid: 5849358
Leverenz, M., Merten, C., Dreuw, A., & Bach, T. (2019). Lewis acid catalyzed enantioselective photochemical rearrangements on the single potential energy surface. Journal of the American Chemical Society, 141(51), 20053–20057. https://doi.org/10.1021/jacs.9b12068
doi: 10.1021/jacs.9b12068
pubmed: 31814393
pmcid: 6935867
Du, J., Skubi, K. L., Schultz, D. M., & Yoon, T. P. (2014). A dual-catalysis approach to enantioselective [2+2] photocycloadditions using visible light. Science, 344(6182), 392–396. https://doi.org/10.1126/science.1251511
doi: 10.1126/science.1251511
pubmed: 24763585
pmcid: 4544835
Blum, T. R., Miller, Z. D., Bates, D. M., Guzei, I. A., & Yoon, T. P. (2016). Enantioselective photochemistry through Lewis acid-catalyzed triplet energy transfer. Science, 354(6318), 1391–1395. https://doi.org/10.1126/science.aai8228
doi: 10.1126/science.aai8228
pubmed: 27980203
pmcid: 5501084
Huo, H., Shen, X., Wang, C., Zhang, L., Röse, P., Chen, L. A., Harms, K., Marsch, M., Hilt, G., & Meggers, E. (2014). Asymmetric photoredox transition-metal catalysis activated by visible light. Nature, 515, 100–103. https://doi.org/10.1038/nature13892
doi: 10.1038/nature13892
pubmed: 25373679
Burg, F., & Bach, T. (2019). Lactam hydrogen bonds as control elements in enantioselective transition-metal-catalyzed and photochemical reactions. The Journal of Organic Chemistry, 84, 8815–8836. https://doi.org/10.1021/acs.joc.9b01299
doi: 10.1021/acs.joc.9b01299
pubmed: 31181155
Groβkopf, J., Kratz, T., Rigotti, T., & Bach, T. (2020). Enantioselective photochemical reactions enabled by triplet energy transfer. Chemical Reviews. https://doi.org/10.1021/acs.chemrev.1c00272
doi: 10.1021/acs.chemrev.1c00272
Strieth-Kalthoff, F., & Glorius, F. (2020). Triplet energy transfer photocatalysis: unlocking the next level. Chem, 6, 1888–1903. https://doi.org/10.1016/j.chempr.2020.07.010
doi: 10.1016/j.chempr.2020.07.010
Shi, Q., & Ye, J. (2020). Deracemization enabled by visible-light photocatalysis. Angewandte Chemie International Edition, 59, 4998–5001. https://doi.org/10.1002/anie.201914858
doi: 10.1002/anie.201914858
pubmed: 32031314
Maturi, M. M., & Bach, T. (2014). Enantioselective catalysis of the intermolecular [2+2] photocycloaddition between 2-pyridones and acetylenedicarboxylates. Angewandte Chemie International Edition, 53, 7661–7664. https://doi.org/10.1002/anie.201403885
doi: 10.1002/anie.201403885
pubmed: 24888463
Müller, C., Bauer, A., & Bach, T. (2009). Light-driven enantioselective organocatalysis. Angewandte Chemie International Edition, 48, 6640–6642. https://doi.org/10.1002/anie.200901603
doi: 10.1002/anie.200901603
pubmed: 19472260
Skubi, K. L., Kidd, J. B., Jung, H., Guzei, I. A., Baik, M.-H., & Yoon, T. P. (2017). Enantioselective excited-state photoreactions controlled by a chiral hydrogen-bonding iridium sensitizer. Journal of the American Chemical Society, 139(47), 17186–17192. https://doi.org/10.1021/jacs.7b10586
doi: 10.1021/jacs.7b10586
pubmed: 29087702
pmcid: 5749223
Zheng, J., Swords, W. B., Jung, H., Skubi, K. L., Kidd, J. B., Meyer, G. J., Baik, M.-H., & Yoon, T. P. (2019). Enantioselective intermolecular excited-state photoreactions using a chiral ir triplet sensitizer: separating association from energy transfer in asymmetric photocatalysis. Journal of the American Chemical Society, 141(34), 13625–13634. https://doi.org/10.1021/jacs.9b06244
doi: 10.1021/jacs.9b06244
pubmed: 31329459
pmcid: 7590369
Vallavoju, N., Selvakumar, S., Jockusch, S., Sibi, M. P., & Sivaguru, J. (2014). Enantioselective organo-photocatalysis mediated by atropisomeric thiourea derivatives. Angewandte Chemie International Edition, 53, 5604–5608. https://doi.org/10.1002/anie.201310940
doi: 10.1002/anie.201310940
pubmed: 24740511
For a review on [2+2] photocycloadditions employing supramolecular photochemistry, see: Ramamurthy, V., & Sivaguru, J. (2016) Supramolecular Photochemistry as a Potential Synthetic Tool: Photocycloaddition. Chemical Reviews 116, 9914–9993. https://doi.org/10.1021/acs.chemrev.6b00040
Vallavoju, N., Selvakumar, S., Pemberton, B. C., Jockusch, S., Sibi, M. P., & Sivaguru, J. (2016). Organophotocatalysis: Insights into the mechanistic aspects of thiourea-mediated intermolecular [2+2] photocycloadditions. Angewandte Chemie International Edition, 55, 5446–5451. https://doi.org/10.1002/anie.201600596
doi: 10.1002/anie.201600596
pubmed: 27005562
Hölzl-Hobmeier, A., Bauer, A., Silva, A. V., Huber, S. M., Bannwarth, C., & Bach, T. (2018). Catalytic deracemization of chiral allenes by sensitized excitation with visible light. Nature, 564, 240–243. https://doi.org/10.1038/s41586-018-0755-1
doi: 10.1038/s41586-018-0755-1
pubmed: 30542163
Plaza, M., Jandl, C., & Bach, T. (2020). Photochemical deracemization of allenes and subsequent chirality transfer. Angewandte Chemie International Edition, 59, 12785–12788. https://doi.org/10.1002/anie.202004797
doi: 10.1002/anie.202004797
pubmed: 32390291
Li, X., Kutta, R. J., Jandl, C., Bauer, A., Nuernberger, P., & Bach, T. (2020). Photochemically induced ring opening of spirocyclopropyl oxindoles: Evidence for a triplet 1,3-diradical intermediate and deracemization by a chiral sensitizer. Angewandte Chemie International Edition, 59, 21640–21647. https://doi.org/10.1002/anie.202008384
doi: 10.1002/anie.202008384
pubmed: 32757341
Wimberger, L., Kratz, T., & Bach, T. (2019). Photochemical deracemization of chiral sulfoxides catalyzed by a hydrogen-bonding xanthone sensitizer. Synthesis, 51(23), 4417–4416. https://doi.org/10.1055/s-0039-1690034
doi: 10.1055/s-0039-1690034
Shin, N. Y., Ryss, J. M., Zhang, X., Miller, S. J., & Knowles, R. R. (2019). Light-driven deracemization enabled by excited-state electron transfer. Science, 366, 364–369. https://doi.org/10.1126/science.aay2204
doi: 10.1126/science.aay2204
pubmed: 31624212
pmcid: 6939311
Gilday, L. G., Robinson, S. W., Barendt, T. A., Langton, M. J., Mullaney, B. R., & Beer, P. D. (2015). Halogen bonding in supramolecular chemistry. Chemical Reviews, 115, 7118–7195. https://doi.org/10.1021/cr500674c
doi: 10.1021/cr500674c
pubmed: 26165273
Deng, J.-H., Luo, J., Mao, Y.-L., Lai, S., Gong, Y.-N., Zhong, D.-C., & Lu, T.-B. (2020). π-π stacking interactions: Non-negligible forces for stabilizing porous supramolecular frameworks. Science Advances. https://doi.org/10.1126/sciadv.aax9976
doi: 10.1126/sciadv.aax9976
pubmed: 33310853
pmcid: 7732193
Crisenza, G. E. M., Mazarella, D., & Melchiorre, P. (2020). Synthetic methods driven by the photoactivity of electron donor-acceptor complexes. Journal of the American Chemical Society, 142(12), 5461–5476. https://doi.org/10.1021/jacs.0c01416
doi: 10.1021/jacs.0c01416
pubmed: 32134647
pmcid: 7099579
Kandukuri, S. R., Bahamonde, A., Chatterjee, I., Jurberg, I. D., Escudero-Adán, E. C., & Melchiorre, P. (2015). X-ray characterization of an electron donor-acceptor complex that drives the photochemical alkylation of indoles. Angewandte Chemie International Edition, 54, 1485–1489. https://doi.org/10.1002/anie.201409529
doi: 10.1002/anie.201409529
pubmed: 25475488
Wu, J., Grant, P. S., Li, X., Noble, A., & Aggarwal, V. K. (2019). Catalyst-free deaminative functionalizations of primary amines by photoinduced single-electron transfer. Angewandte Chemie International Edition, 58, 5697–5701. https://doi.org/10.1002/anie.201814452
doi: 10.1002/anie.201814452
pubmed: 30794331
Fu, M.-C., Shang, R., Zhao, B., Wang, B., & Fu, Y. (2019). Photocatalytic decarboxylative alkylations mediated by triphenylphosphine and sodium iodide. Science, 363, 1429–1434. https://doi.org/10.1126/science.aav3200
doi: 10.1126/science.aav3200
pubmed: 30923218
For a review on cation-π interactions, see: Yamada, S. (2018) Cation−π interactions in organic synthesis. Chemical Reviews 118, 11353−11432. https://doi.org/10.1021/acs.chemrev.8b00377
Duchemin, N., Skiredj, A., Mansot, J., Leblanc, K., Vassuer, J. J., Beniddir, M. A., Evanno, L., Poupon, E., Smietana, M., & Arseniyadis, S. (2018). DNA-templated [2+2] photocycloaddition: A straightforward entry into the aplysinopsin family of natural products. Angewandte Chemie International Edition, 57(36), 11786–11791. https://doi.org/10.1002/anie.201806357
doi: 10.1002/anie.201806357
pubmed: 29989287
Percástegi, E. G., Ronson, T. K., & Nitschke, J. R. (2020). Design and applications of water-soluble coordination cages. Chemical Reviews, 120, 13480–13544. https://doi.org/10.1021/acs.chemrev.0c00672
doi: 10.1021/acs.chemrev.0c00672
Uchikura, T., Oshima, M., Kawasaki, M., Takahashi, K., & Iwasawa, N. (2020). Supramolecular photocatalysis by utilizing the host-guest charge-transfer interaction: Visible-light-induced generation of triplet anthracenes for [4+2] cycloaddition reactions. Angewandte Chemie International Edition, 59(19), 7403–7408. https://doi.org/10.1002/anie.201916732
doi: 10.1002/anie.201916732
pubmed: 32043287
Zuo, M., Verlmurugan, K., Wang, K., Tian, X., & Hu, X.-Y. (2021). Insight into functionalized-macrocycles-guided supramolecular photocatalysis. Beilstein Journal of Organic Chemistry, 17, 139–155. https://doi.org/10.3762/bjoc.17.15
doi: 10.3762/bjoc.17.15
pubmed: 33564325
pmcid: 7849235
Ji, J., Wu, W., Liang, W., Cheng, G., Matsushita, R., Yan, Z., Wei, X., Rao, M., Yuan, D. Q., Fukuhara, G., Mori, T., Inoue, Y., & Yang, C. (2019). An ultimate stereocontrol in supramolecular photochirogenesis: Photocyclodimerization of 2-anthracenecarboxylate mediated by sulfur-linked beta-cyclodextrin dimers. Journal of the American Chemical Society, 141(23), 9225–9238. https://doi.org/10.1021/jacs.9b01993
doi: 10.1021/jacs.9b01993
pubmed: 31117644
Winkler, C. K., Schrittwieser, J. H., & Kroutil, W. (2021). Power of biocatalysis for organic synthesis. ACS Central Science, 7, 55–71. https://doi.org/10.1021/acscentsci.0c01496
doi: 10.1021/acscentsci.0c01496
pubmed: 33532569
pmcid: 7844857
Özgen, F. F., Runda, M. E., & Schmidt, S. (2021). Photo-biocatalytic cascades: Combining chemical and enzymatic transformations fueled by light. ChemBioChem, 22, 790–806. https://doi.org/10.1002/cbic.202000587
doi: 10.1002/cbic.202000587
pubmed: 32961020
Sandoval, B. A., & Hyster, T. K. (2020). Emerging strategies for expanding the toolbox of enzymes in biocatalysis. Current Opinion in Chemical Biology, 55, 45–51. https://doi.org/10.1016/j.cbpa.2019.12.006
doi: 10.1016/j.cbpa.2019.12.006
pubmed: 31935627
pmcid: 7769163
Emmanuel, M. A., Greensberg, N. R., Oblinsky, D. G., & Hyster, T. K. (2016). Accessing non-natural reactivity by irradiating nicotinamide-dependent enzymes with light. Nature, 540, 414–417. https://doi.org/10.1038/nature20569
doi: 10.1038/nature20569
pubmed: 27974767
Biegasiewicz, K. F., Cooper, S. J., Gao, X., Oblinsky, D. G., Kim, J. H., Garfinkle, S. E., Joyce, L. A., Sandoval, B. A., Scholes, G. D., & Hyster, T. K. (2019). Photoexcitation of flavoenzymes enables a stereoselective radical cyclization. Science, 364(6446), 1166–1169. https://doi.org/10.1126/science.aaw1143
doi: 10.1126/science.aaw1143
pubmed: 31221855
pmcid: 7028431
Naumann, R., Lehmann, F., & Goez, M. (2018). Generating hydrated electrons for chemical syntheses by using a green light-emitting diode (LED). Angewandte Chemie International Edition, 57(4), 1078–1081. https://doi.org/10.1002/anie.201711692
doi: 10.1002/anie.201711692
pubmed: 29205956
Cybularczyk-Cecotka, M., Szczepanik, J., & Giedyk, M. (2020). Photocatalytic strategies for the activation of organic chlorides. Nature Catalysis, 3, 872–886. https://doi.org/10.1038/s41929-020-00515-8
doi: 10.1038/s41929-020-00515-8
Giedyk, M., Narobe, R., Weiß, S., Touraud, D., Kunz, W., & König, B. (2020). Photocatalytic strategies for the activation of organic chlorides. Nature Catalysis, 3, 40–47. https://doi.org/10.1038/s41929-020-00515-8
doi: 10.1038/s41929-020-00515-8