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    Arene–Alkene Cycloaddition
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    Department of Chemistry, University of Fribourg, Chemin du Musée 9, CH-1700 Fribourg, Switzerland
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    Cite this: Chem. Rev. 2016, 116, 17, 9816–9849
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    https://doi.org/10.1021/acs.chemrev.6b00005
    Published June 24, 2016
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    Abstract

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    Cycloadditions are among the most efficient chemical processes, combining atom economy, stereospecificity, and the ability to generate molecular complexity in a single step. Aromatic rings would in principle be ideal reaction partners, as they contain, at least from the topological point of view, both olefinic and diene subunits; however, the stability of the conjugated aromatic system would be broken by cycloaddition reactions, which are therefore rarely applied, because kinetics and thermodynamics hinder the process. From that aspect, photochemical activation opens interesting perspectives, as one can selectively provide excess energy to one of the reactants but not to the product, thus preventing thermal back reaction. Indeed, aromatic rings show a rich photochemistry, ranging from isomerizations, substitutions, and additions to cycloadditions. In this review, we will focus on cycloadditions, covering literature from early observations up to the present.

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    3. Zohaib Siddiqi, David Sarlah. Reimagining Dearomatization: Arenophile-Mediated Single-Atom Insertions and π-Extensions. Accounts of Chemical Research 2025, 58 (7) , 1134-1150. https://doi.org/10.1021/acs.accounts.5c00035
    4. Audrey Gilbert, Julian Zuber, Thorsten Bach. Intramolecular ortho Photocycloaddition of 4-Substituted 7-(4′-Alkenyloxy)-1-indanones and Ensuing Reaction Cascades. The Journal of Organic Chemistry 2025, 90 (11) , 4099-4107. https://doi.org/10.1021/acs.joc.5c00171
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    7. Souvik Adak, Sarah E. Braley, M. Kevin Brown. Photochemical Reduction of Quinolines with γ-Terpinene. Organic Letters 2024, 26 (1) , 401-405. https://doi.org/10.1021/acs.orglett.3c04096
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    10. Sajan Pradhan, Fahimeh Mohammadi, Jean Bouffard. Skeletal Transformation of Unactivated Arenes Enabled by a Low-Temperature Dearomative (3 + 2) Cycloaddition. Journal of the American Chemical Society 2023, 145 (22) , 12214-12223. https://doi.org/10.1021/jacs.3c02314
    11. Roman Kleinmans, Subhabrata Dutta, Kristers Ozols, Huiling Shao, Felix Schäfer, Rebecca E. Thielemann, Hok Tsun Chan, Constantin G. Daniliuc, Kendall N. Houk, Frank Glorius. ortho-Selective Dearomative [2π + 2σ] Photocycloadditions of Bicyclic Aza-Arenes. Journal of the American Chemical Society 2023, 145 (22) , 12324-12332. https://doi.org/10.1021/jacs.3c02961
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    14. Hao Zhang, Xian He, Xiang-Ai Yuan, Shouyun Yu. Kinetic Resolution of 2-Cinnamylpyrrolines Enabled by Photoexcited Chiral Copper Complex-Mediated Alkene E → Z Isomerization. ACS Catalysis 2023, 13 (5) , 2857-2866. https://doi.org/10.1021/acscatal.2c06183
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    39. Luke D. Elliott, Kevin I. Booker-Milburn. Photochemically Produced Aminocyclobutanes as Masked Dienes in Thermal Electrocyclic Cascade Reactions. Organic Letters 2019, 21 (5) , 1463-1466. https://doi.org/10.1021/acs.orglett.9b00211
    40. Min Zhu, Chao Zheng, Xiao Zhang, Shu-Li You. Synthesis of Cyclobutane-Fused Angular Tetracyclic Spiroindolines via Visible-Light-Promoted Intramolecular Dearomatization of Indole Derivatives. Journal of the American Chemical Society 2019, 141 (6) , 2636-2644. https://doi.org/10.1021/jacs.8b12965
    41. Clément Michelin, Norbert Hoffmann. Photosensitization and Photocatalysis—Perspectives in Organic Synthesis. ACS Catalysis 2018, 8 (12) , 12046-12055. https://doi.org/10.1021/acscatal.8b03050
    42. Leiming Tian, Isaac J. Krauss. Stereoselective Homocrotylation of Aldehydes: Enantioselective Synthesis of Allylic-Substituted Z/E-Alkenes. Organic Letters 2018, 20 (21) , 6730-6735. https://doi.org/10.1021/acs.orglett.8b02837
    43. John A. Milligan, James P. Phelan, Viktor C. Polites, Christopher B. Kelly, Gary A. Molander. Radical/Polar Annulation Reactions (RPARs) Enable the Modular Construction of Cyclopropanes. Organic Letters 2018, 20 (21) , 6840-6844. https://doi.org/10.1021/acs.orglett.8b02968
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    47. Charlotte A. Clark, Darren S. Lee, Stephen J. Pickering, Martyn Poliakoff, Michael W. George. UV PhotoVap: Demonstrating How a Simple and Versatile Reactor Based on a Conventional Rotary Evaporator Can Be Used for UV Photochemistry. Organic Process Research & Development 2018, 22 (5) , 595-599. https://doi.org/10.1021/acs.oprd.8b00037
    48. Lucas W. Hernandez, Ulrich Klöckner, Jola Pospech, Lilian Hauss, David Sarlah. Nickel-Catalyzed Dearomative trans-1,2-Carboamination. Journal of the American Chemical Society 2018, 140 (13) , 4503-4507. https://doi.org/10.1021/jacs.8b01726
    49. Andreas Zech, Thorsten Bach. Photochemical Reaction Cascade from O-Pent-4-enyl-Substituted Salicylates to Complex Multifunctional Scaffolds. The Journal of Organic Chemistry 2018, 83 (6) , 3069-3077. https://doi.org/10.1021/acs.joc.8b00238
    50. Hajime Maeda, Hisashi Sakurai, and Masahito Segi . Intramolecular Photoreactions of 9-Cyanophenanthrene-Linked Arylcyclopropanes. ACS Omega 2017, 2 (12) , 8697-8708. https://doi.org/10.1021/acsomega.7b01439
    51. Dmitry M. Kuznetsov and Andrei G. Kutateladze . Step-Economical Photoassisted Diversity-Oriented Synthesis: Sustaining Cascade Photoreactions in Oxalyl Anilides to Access Complex Polyheterocyclic Molecular Architectures. Journal of the American Chemical Society 2017, 139 (46) , 16584-16590. https://doi.org/10.1021/jacs.7b07598
    52. Yang Li, Jin-Xia Li, Xuan-Hui Ouyang, Qiu-An Wang, and Jin-Heng Li . Manganese-Catalyzed Intermolecular Oxidative Annulation of Alkynes with γ-Vinyl Aldehydes: An Entry to Bridged Carbocyclic Systems. Organic Letters 2017, 19 (22) , 6172-6175. https://doi.org/10.1021/acs.orglett.7b03086
    53. Darren S. Lee, Zacharias Amara, Charlotte A. Clark, Zeyuan Xu, Bruce Kakimpa, Herve P. Morvan, Stephen J. Pickering, Martyn Poliakoff, and Michael W. George . Continuous Photo-Oxidation in a Vortex Reactor: Efficient Operations Using Air Drawn from the Laboratory. Organic Process Research & Development 2017, 21 (7) , 1042-1050. https://doi.org/10.1021/acs.oprd.7b00153
    54. Chieh-Kai Chan, Yu-Hsin Chen, Yu-Lin Tsai, and Meng-Yang Chang . Synthesis of Substituted 1,6-Diarylnaphthalenes via a Tandem Claisen Rearrangement and Ene Reaction Protocol. The Journal of Organic Chemistry 2017, 82 (6) , 3317-3326. https://doi.org/10.1021/acs.joc.7b00108
    55. Pramod Rai, Sanghamitra Naik, Kriti Gupta, Kakoli Maji, Garima Jindal, Biplab Maji. Visible light-driven dearomative meta-cycloadditions of 2-acetonaphthalenes via triplet energy transfer cascade. Nature Communications 2025, 16 (1) https://doi.org/10.1038/s41467-025-58285-5
    56. Jie Yang, Zhongshu Li, Xiantao Wu, Jie Chen, Sisi Huang, Yu-Lin Lu, Zhiwei Jiao, Cheng-Yong Su. Enantioselective dearomative ortho-cycloaddition transformation of unactivated arenes by cage-confined visible-light photocatalysis. Nature Communications 2025, 16 (1) https://doi.org/10.1038/s41467-025-59176-5
    57. Chun‐Yu Nong, Xiu‐Qing Mo, Jin‐He Zhao, Lu Lei, Lu Ma, Dong‐Liang Mo. Three‐Component Cycloadditions to Prepare Isooxazoline‐Fused Furo[3,2‐b]quinolines. European Journal of Organic Chemistry 2025, 28 (17) https://doi.org/10.1002/ejoc.202500007
    58. Yi-Ping Cai, Shi-Ru Chen, Qin-Hua Song. Successive energy-transfer catalytic dearomative reactions of quinolines with bicyclo[1.1.0]butanes for the synthesis of pyridine-fused 3D complicated molecules. Organic Chemistry Frontiers 2025, 12 (8) , 2676-2686. https://doi.org/10.1039/D5QO00205B
    59. Jiayuan Li, Zeyu Zhang, Yaping Yi, Chanjuan Xi. Visible-light-induced photoredox-catalyzed dearomative dicarboxylation of arenes using formate and CO 2. Green Chemistry 2025, 27 (13) , 3443-3450. https://doi.org/10.1039/D5GC00240K
    60. Ying Chen, Yumei Shu, Minhua Ai, Wenbiao Chen, Chengwen Liu, Songyi Zhang, Shaojie Wang, Haopeng Shi, Ji-Jun Zou, Lun Pan. Mechanism of Brønsted-acid-promoted self-photosensitized [2+2] cycloaddition for synthesis of high-performance bio-spiral fuel. Green Energy & Environment 2025, 10 (3) , 585-597. https://doi.org/10.1016/j.gee.2024.05.006
    61. Yu Chen, Sheng‐Nan Sun, Xiao‐Hong Chen, Ming‐Lin Chen, Jiao‐Min Lin, Qian Niu, Shun‐Li Li, Jiang Liu, Ya‐Qian Lan. Predesign of Covalent‐Organic Frameworks for Efficient Photocatalytic Dehydrogenative Cross‐Coupling Reaction. Advanced Materials 2025, 37 (6) https://doi.org/10.1002/adma.202413638
    62. Tongtong Zhu, Xuhui Cui, Wenjun Ma, Xiujuan Qi, Hao Wei. Synthesis of naphthalene derivatives via nitrogen-to-carbon transmutation of isoquinolines. Science Advances 2025, 11 (5) https://doi.org/10.1126/sciadv.ads5928
    63. Zhenquan Fang, Chengyan Wen, Xinghua Zhang, Lungang Chen, Qi Zhang, Jianguo Liu, Longlong Ma. Advance, challenge, and outlook of carbon-increasing strategies for producing sustainable high-energy-density jet fuels from lignocellulosic derivatives. The Innovation Energy 2025, , 100093. https://doi.org/10.59717/j.xinn-energy.2025.100093
    64. M. Okumura. 4.1 Arenophile-Mediated Photochemical Dearomative Functionalization. 2025https://doi.org/10.1055/sos-SD-245-00051
    65. Bo Yang, Jiawei Xie, Yuxuan Liang, Xiumei Ma, Huyao Ge, Xueping Wang, Zhaohui Wang, Qiuyu Zhang, Ji-Jun Zou, Junjian Xie. Self-photosensitized cycloaddition induced synthesis of a high-density fuel with ultra-low freezing point using bulk bio-benzaldehyde and furans. Green Chemistry 2025, 62 https://doi.org/10.1039/D4GC06345G
    66. Norbert Hoffmann, Arthur Desvals. Photocycloadditions of aromatic compounds with alkenes: the role of spin multiplicity. 2024, 469-481. https://doi.org/10.1039/9781837676552-00469
    67. Norbert Hoffmann, Mario Andrés Gomez Fernandez, Arthur Desvals, Corentin Lefebvre, Clément Michelin, Mohammed Latrache. Photochemical reactions of biomass derived platform chemicals. Frontiers in Chemistry 2024, 12 https://doi.org/10.3389/fchem.2024.1485354
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    74. João V. Schober, Croix J. Laconsay, Judy I. Wu. Is aromaticity loss necessary for transition-metal promoted arene–alkene cycloadditions?. Chemical Science 2024, 15 (43) , 18093-18098. https://doi.org/10.1039/D4SC05337K
    75. Yang Wang, Ji‐Chen Yin, Yu‐Wei Zhang, Yuzhe Zhang, Feng Shi. Hypervalent Iodine‐Mediated Regioselective Dearomatization of Non‐Activated Arenes. Advanced Synthesis & Catalysis 2024, 366 (20) , 4253-4259. https://doi.org/10.1002/adsc.202400852
    76. Yaping Yi, Chanjuan Xi. Photo-catalyzed dearomative coupling of benzylmalonates and alkynes with CO2 leading to spiro-1,4-cyclohexadiene carboxylic acids. Green Synthesis and Catalysis 2024, 33 https://doi.org/10.1016/j.gresc.2024.09.003
    77. Shupeng Liu, Tianyi Xu, Yuting Liu, Youliang Wang. Dearomative Intramolecular meta ‐Thermocycloadditions of Benzene Rings via Wheland Intermediates. Angewandte Chemie 2024, 136 (35) https://doi.org/10.1002/ange.202407841
    78. Shupeng Liu, Tianyi Xu, Yuting Liu, Youliang Wang. Dearomative Intramolecular meta ‐Thermocycloadditions of Benzene Rings via Wheland Intermediates. Angewandte Chemie International Edition 2024, 63 (35) https://doi.org/10.1002/anie.202407841
    79. Aljazy A. A. Alshammari, Joseph W. Boyd, Nicola Greaves, Jason G. Kettle, John E. McKendrick, Lewis G. Parker, Andrew T. Russell, Abubakar Sani, Christopher D. Smith. Effect of Tether Length on endo / exo Stereoselectivity in Alkene–Arene meta ‐Photocycloaddition Reactions towards the Aphidocolin/Stemodin Scaffolds. European Journal of Organic Chemistry 2024, 27 (30) https://doi.org/10.1002/ejoc.202400463
    80. Andrea Serafino, Giovanni Maestri. A Complementary Route for Alkene–Arene para-Cycloadditions by Visible-Light-Promoted Triplet Sensitization of Allenamides. Synlett 2024, 35 (12) , 1333-1337. https://doi.org/10.1055/a-2136-3947
    81. Peng Ji, Kuaikuai Duan, Menglong Li, Zhiyuan Wang, Xiang Meng, Yueteng Zhang, Wei Wang. Photochemical dearomative skeletal modifications of heteroaromatics. Chemical Society Reviews 2024, 53 (12) , 6600-6624. https://doi.org/10.1039/D4CS00137K
    82. Ying Chen, Xinfang Zhang, Xiaolei Guo, Minhua Ai, Yumei Shu, Chengxiang Shi, Xiangwen Zhang, Ji‐Jun Zou, Lun Pan. Mechanism and kinetics of self‐sensitized photocycloaddition of cyclohexenone and norbornene. AIChE Journal 2024, 70 (5) https://doi.org/10.1002/aic.18369
    83. Zhi-Yu Liao, Fan Gao, Yu-Hang Ye, Qian-Hui Yu, Cui Yang, Qing-Yu Luo, Fei Du, Bin Pan, Wen-Wu Zhong, Wu Liang. Construction of cyclobutane-fused tetracyclic skeletons via substrate-dependent EnT-enabled dearomative [2+2] cycloaddition of benzofurans (benzothiophenes)/maleimides. Chemical Communications 2024, 60 (33) , 4455-4458. https://doi.org/10.1039/D4CC00690A
    84. Peng Yan, Simone Stegbauer, Qinqin Wu, Elena Kolodzeiski, Christopher J. Stein, Ping Lu, Thorsten Bach. Enantioselective Intramolecular ortho Photocycloaddition Reactions of 2‐Acetonaphthones. Angewandte Chemie 2024, 136 (13) https://doi.org/10.1002/ange.202318126
    85. Peng Yan, Simone Stegbauer, Qinqin Wu, Elena Kolodzeiski, Christopher J. Stein, Ping Lu, Thorsten Bach. Enantioselective Intramolecular ortho Photocycloaddition Reactions of 2‐Acetonaphthones. Angewandte Chemie International Edition 2024, 63 (13) https://doi.org/10.1002/anie.202318126
    86. Bohang An, Hao Cui, Chao Zheng, Ji-Lin Chen, Feng Lan, Shu-Li You, Xiao Zhang. Tunable C–H functionalization and dearomatization enabled by an organic photocatalyst. Chemical Science 2024, 15 (11) , 4114-4120. https://doi.org/10.1039/D4SC00120F
    87. Alessandro Cerveri, Gabriele Scarica, Sara Sparascio, Matteo Hoch, Maurizio Chiminelli, Matteo Tegoni, Stefano Protti, Giovanni Maestri. Boosting Energy‐Transfer Processes via Dispersion Interactions. Chemistry – A European Journal 2024, 30 (15) https://doi.org/10.1002/chem.202304010
    88. Jinxiu Hu, Xianlong Liu, Yi Liu, Kang Xue, Chengxiang Shi, Xiangwen Zhang, Li Wang, Ji-Jun Zou, Lun Pan. Photoinduced transposed Paternò-Büchi reaction for effective synthesis of high-performance jet fuel. Chinese Journal of Chemical Engineering 2024, 67 , 39-48. https://doi.org/10.1016/j.cjche.2023.09.014
    89. Qian-Qian Hu, Jie Chen, Yang Yang, Hui Yang, Ling Zhou. Strain-release transformations of bicyclo[1.1.0]butanes and [1.1.1]propellanes. Tetrahedron Chem 2024, 9 , 100070. https://doi.org/10.1016/j.tchem.2024.100070
    90. Maurizio Chiminelli, Gabriele Scarica, Andrea Serafino, Luciano Marchiò, Rosanna Viscardi, Giovanni Maestri. Visible-Light-Promoted Tandem Skeletal Rearrangement/Dearomatization of Heteroaryl Enallenes. Molecules 2024, 29 (3) , 595. https://doi.org/10.3390/molecules29030595
    91. Ting‐Ting Song, Yong‐Kang Mei, Yan Liu, Xiao‐Yu Wang, Shi‐Yu Guo, Ding‐Wei Ji, Boshun Wan, Weiming Yuan, Qing‐An Chen. Construction of Bridged Benzazepines via Photo‐Induced Dearomatization. Angewandte Chemie 2024, 136 (2) https://doi.org/10.1002/ange.202314304
    92. Ting‐Ting Song, Yong‐Kang Mei, Yan Liu, Xiao‐Yu Wang, Shi‐Yu Guo, Ding‐Wei Ji, Boshun Wan, Weiming Yuan, Qing‐An Chen. Construction of Bridged Benzazepines via Photo‐Induced Dearomatization. Angewandte Chemie International Edition 2024, 63 (2) https://doi.org/10.1002/anie.202314304
    93. Norbert Hoffmann. Diastereoselectivity in Photochemistry. 2024, 3-29. https://doi.org/10.1016/B978-0-32-390644-9.00113-X
    94. Christian G. Bochet. Photochemical Key Steps in Natural Products Synthesis. 2024, 251-269. https://doi.org/10.1016/B978-0-32-390644-9.00148-7
    95. Norbert Hoffmann. Di-π-methane, Oxa-di-π-methane, and Aza-di-π-methane Photoisomerization. 2024https://doi.org/10.1016/B978-0-323-96025-0.00103-4
    96. Maurizio Chiminelli, Gabriele Scarica, Davide Balestri, Luciano Marchiò, Nicola Della Ca’, Giovanni Maestri. The visible-light-promoted intermolecular para-cycloadditions of allenamides on naphthalene. Tetrahedron Chem 2023, 8 , 100053. https://doi.org/10.1016/j.tchem.2023.100053
    97. Lei Tang, Yuanjiu Xiao, Feng Wu, Jin‐Lan Zhou, Tong‐Tong Xu, Jian‐Jun Feng. Silver‐Catalyzed Dearomative [2π+2σ] Cycloadditions of Indoles with Bicyclobutanes: Access to Indoline Fused Bicyclo[2.1.1]hexanes**. Angewandte Chemie 2023, 135 (48) https://doi.org/10.1002/ange.202310066
    98. Lei Tang, Yuanjiu Xiao, Feng Wu, Jin‐Lan Zhou, Tong‐Tong Xu, Jian‐Jun Feng. Silver‐Catalyzed Dearomative [2π+2σ] Cycloadditions of Indoles with Bicyclobutanes: Access to Indoline Fused Bicyclo[2.1.1]hexanes**. Angewandte Chemie International Edition 2023, 62 (48) https://doi.org/10.1002/anie.202310066
    99. Angshuman Palai, Pramod Rai, Biplab Maji. Rejuvenation of dearomative cycloaddition reactions via visible light energy transfer catalysis. Chemical Science 2023, 14 (43) , 12004-12025. https://doi.org/10.1039/D3SC04421A
    100. Pritishree Panigrahi, Subhendu Ghosh, Tamanna Khandelia, Raju Mandal, Bhisma K. Patel. Isoxazole as a nitrile synthon: en routes to the ortho -alkenylated isoxazole and benzonitrile with allyl sulfone catalyzed by Ru( ii ). Chemical Communications 2023, 59 (70) , 10536-10539. https://doi.org/10.1039/D3CC02996D
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    Cite this: Chem. Rev. 2016, 116, 17, 9816–9849
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