Electrochemical oxidation-induced benzylic C(sp3)–H functionalization towards the atom-economic synthesis of oxazole heterocycles

Na Yang, Anni Li, Hui Gao, Li-Mei Liao, Yu-Ping Yang, Pei-Long Wang and Hongji Li

Green Chem., 2023, 25, 5128
DOI: 10.1039/D2GC04782A

Metallaphotoredox catalysis for sp3C–H functionalizations through hydrogen atom transfer (HAT)

Jingchang Zhang and Magnus Rueping

Chem. Soc. Rev., 2023, 52, 4099
DOI: 10.1039/D3CS00023K

C–H functionalization through benzylic deprotonation with π-coordination or cation–π-interactions

Hui Zhu(s), Yu Wu, Jianyou Mao, Jingkai Xu, Patrick J. Walsh and Hang Shi

Chem. Soc. Rev., 2025, 54, 2520
DOI: 10.1039/D4CS00466C

Rapid construction of a polysubstituted “caged” oxa-bishomocubane framework from vinylidenecyclopropanes through a sequential dual catalysis of copper(i) and visible-light-induced photosensitization

Yan-Shun Zhang, Yin Wei and Min Shi

Org. Chem. Front., 2022, 9, 3739
DOI: 10.1039/D2QO00508E

Advances and developments in transition metal-free benzylic C(sp3)–H activation/functionalization reactions

Fatemeh Doraghi, Shahab Kermaninia, Elika Salehi Ghalehsefid, Bagher Larijani and Mohammad Mahdavi

RSC Adv., 2025, 15, 14691
DOI: 10.1039/D5RA00361J

The photocatalytic selective 1,2-hydroxyacylmethylation of 1,3-dienes with sulfur ylides as the source of alkyl radicals

Shuang-Hua Xu, Dong-Mei Yan, Li Rao, Min Jiang, Ya-Li Wu, Wen-Jing Xiao and Jia-Rong Chen

Org. Chem. Front., 2022, 9, 3747
DOI: 10.1039/D2QO00383J

Metal- and oxidant-free carbonylation of benzylic and allylic C–H bonds with H2O via dual oxidative radical-polar crossover

Xiaona Yang, Bingjie Ren, Hongyu Guo, Rongfang Liu and Rong Zhou

Green Chem., 2024, 26, 10344
DOI: 10.1039/D4GC02381A

Bromine-radical-induced Csp2–H difluoroalkylation of quinoxalinones and hydrazones through visible-light-promoted Csp3–Br bond homolysis

Chuan-Hua Qu, Run Huang, Yuan Liu, Tong Liu and Gui-Ting Song

Org. Chem. Front., 2022, 9, 4135
DOI: 10.1039/D2QO00710J

External photocatalyst- and additive-free visible light-driven direct benzylic C–H functionalization with 1,2-diketones

Xiaofeng Yu, Nan Huang, Yuhua Lu, Yanping Huo, Yang Gao, Xianwei Li and Qian Chen

Green Chem., 2025, 27, 13804
DOI: 10.1039/D5GC04600A

Catalyst-free benzylic C(sp3)–H cross-coupling with organotrifluoroborates enabled by electrochemistry

Chao Li, Ran Ding, Heng-Yi Guo, Shuang Xia, Lei Shu, Pei-Long Wang and Hongji Li

Green Chem., 2022, 24, 7883
DOI: 10.1039/D2GC02204D

Stereoselective benzylic C(sp3)–H alkenylation enabled by metallaphotoredox catalysis

Yantao Li, Haonan Bai, Qi Gao, Kai Liu, Jie Han, Weipeng Li, Chengjian Zhu and Jin Xie

Chem. Sci., 2024, 15, 12511
DOI: 10.1039/D4SC02830A

Recent Advances in Electrochemical Benzylic C(sp3)−H Functionalization

Anni Li, Zhengjun He, Qiang Huang and Hongji Li

Eur J Org Chem, 2025, 28
DOI: 10.1002/ejoc.202500275

Dual Nickel/Photoredox‐Catalyzed Site‐Selective Cross‐Coupling of 1,2‐Bis‐Boronic Esters Enabled by 1,2‐Boron Shifts

Hui Wang, Wangyujing Han, Adam Noble and Varinder K. Aggarwal

Angewandte Chemie, 2022, 134
DOI: 10.1002/ange.202207988

Photo- and Copper-Catalyzed Enantioselective Oxidation of Benzylic C(sp3)–H Bonds

Fu Li, Xian-Ming Liu, Jia-Bin Pan, Ling Dai, Yin Yang, Li-Jun Xiao, Chao Fan and Qi-Lin Zhou

J. Am. Chem. Soc., 2025, 147, 19093
DOI: 10.1021/jacs.5c04142

A Quadruple Relay Approach Toward Highly Functionalized Furans: Merging Carbene Insertion, Semi-Pinacol Rearrangement, Decarbonylation, and Paal–Knorr Cyclization

Manickam Bakthadoss, Manickam Surendar, Sivasubramaniyan Kavikumar, Raj Laxmi Shaw, Alapati Yaswanth and Duddu S. Sharada

Org. Lett., 2025, 27, 9606
DOI: 10.1021/acs.orglett.5c02558

Transition Metal-Catalyzed Asymmetric Migratory Allylic C—H Functionalization of Remote Dienes

Jingming Zhang and Zhitao He

Chinese Journal of Organic Chemistry, 2025, 45, 592
DOI: 10.6023/cjoc202406047

Allenyl Radicals in Organic Synthesis: Challenges and Recent Advances

Yang Yu and Jitang Zhang

Eur J Org Chem, 2022, 2022
DOI: 10.1002/ejoc.202201017

Thiobenzoic Acid-Catalyzed Cα–H Cross Coupling of Benzyl Alcohols with α-Ketoacid Derivatives

Kaichi Sato, Hiromichi Egami and Yoshitaka Hamashima

Org. Lett., 2024, 26, 5285
DOI: 10.1021/acs.orglett.4c01594

Photoexcitation of Distinct Divalent Palladium Complexes in Cross‐Coupling Amination Under Air

Rajesh Kancherla, Krishnamoorthy Muralirajan, Sayan Dutta, Kuntal Pal, Bo Li, Bholanath Maity, Luigi Cavallo and Magnus Rueping

Angewandte Chemie, 2024, 136
DOI: 10.1002/ange.202314508

Synthesis of Indolyl Phenyl Diketones through Visible-Light-Promoted Ni-Catalyzed Intramolecular Cyclization/Oxidation Sequence of Ynones

Yufeng Zhou, Yaping Wang, Peidong Xu, Weiwei Han, Heng-Ying Xiong and Guangwu Zhang

ACS Org. Inorg. Au, 2024, 4, 241
DOI: 10.1021/acsorginorgau.3c00060

Expanding the Scope of Chemoselective Reductive Cyclization: Synthesis of Unsubstituted 9H‐Thioxanthenes and 10‐Methyl 9,10‐Dihydroacridines and Beyond

Shashi Kant Verma and Ashok K. Basak

Eur J Org Chem, 2024, 27
DOI: 10.1002/ejoc.202400911

Metallaphotoredox catalysis for sp3 C–H functionalizations through single-electron transfer

Jingchang Zhang and Magnus Rueping

Nat Catal, 2024, 7, 963
DOI: 10.1038/s41929-024-01215-3

CuNi bimetallic nanocatalyst enables sustainable direct carboxylation reactions

Neha Choudhary, Mona Abdelgaid, Giannis Mpourmpakis and Shaikh M. Mobin

Molecular Catalysis, 2022, 530, 112620
DOI: 10.1016/j.mcat.2022.112620

Highly efficient copper-catalyzed benzylic C–H alkoxylation with NFSI

Cheng Zhang and Pu-Sheng Wang

zgkxjsdxxb, 2023, 53, 1202
DOI: 10.52396/JUSTC-2023-0080

Recent advances in semi-heterogenous photocatalysis in organic synthesis

Jia-Cheng Hou, Wei Cai, Hong-Tao Ji, Li-Juan Ou and Wei-Min He

Chinese Chemical Letters, 2025, 36, 110469
DOI: 10.1016/j.cclet.2024.110469

Sustainable Electrochemical Benzylic C−H Oxidation Using MeOH as an Oxygen Source

Meng Xue, Tao Pan, Zhichao Shao, Wenxuan Wang, Hu Li, Lixing Zhao, Xin Zhou and Yuexia Zhang

ChemSusChem, 2024, 17
DOI: 10.1002/cssc.202400028

Ligand‐Enabled [3+2] Annulation of Aromatic Acids with Maleimides by C(sp3)−H and C(sp2)−H Bond Activation

Gouranga Naskar and Masilamani Jeganmohan

Chemistry A European J, 2022, 28
DOI: 10.1002/chem.202200778

Visible-Light-Induced Stoichiometric Coupling of Alkylarenes and Trifluoromethyl Ketones

Qiao-Lin Wang, Huawen Huang, Mengqi Zhu, Tianci Xu, Guojiang Mao and Guo-Jun Deng

Org. Lett., 2023, 25, 3800
DOI: 10.1021/acs.orglett.3c01307

Group 14 Elements Hetero‐Difunctionalizations via Nickel‐Catalyzed Electroreductive Cross‐Coupling

Haifeng Chen, Chen Zhu, Huifeng Yue and Magnus Rueping

Angew Chem Int Ed, 2023, 62
DOI: 10.1002/anie.202306498

Photoredox catalysis of acridinium and quinolinium ion derivatives

Shunichi Fukuzumi, Yong‐Min Lee and Wonwoo Nam

Bulletin Korean Chem Soc, 2025, 46, 4
DOI: 10.1002/bkcs.12922

Designed Iron Catalysts for Allylic C−H Functionalization of Propylene and Simple Olefins

Ruihan Wang, Yidong Wang, Ruiqi Ding, Parker B. Staub, Christopher Z. Zhao, Peng Liu and Yi‐Ming Wang

Angewandte Chemie, 2023, 135
DOI: 10.1002/ange.202216309

Harnessing Photoredox and Weak Brønsted Base Dual Catalysis for Selective C(sp3)–H Bond Activation

Shafrizal R. Atriardi, Yulia Anita and Sang Kook Woo

Synthesis, 2025, 57, 953
DOI: 10.1055/s-0043-1775423

Solvent-Controlled Enantioselective Allylic C–H Alkylation of 2,5-Dihydrofuran via Synergistic Palladium/Nickel Catalysis

Fule Wu, Hongkai Wang, Zhenwei Wu, Yangbin Liu and Xiaoming Feng

J. Am. Chem. Soc., 2025, 147, 16237
DOI: 10.1021/jacs.5c01228

Visible-Light-Induced Three-Component Radical Coupling of Selenocarbamates, Enones, and Allylstannanes with Diphenyl (2,4,6-trimethylbenzoyl)phosphine Oxide

Keita Komine, Yuta Yamazaki, Taiga Iwanaga, Hikaru Sakaguchi, Hayato Fukuda and Jun Ishihara

Synlett, 2023
DOI: 10.1055/a-2214-5512

Thiols as Powerful Atom Transfer Catalyst: Opportunities in Photoredox‐Mediated Reactions

Xiaobo Bao, Wei Yu and Guoli Wang

Adv Synth Catal, 2023, 365, 2299
DOI: 10.1002/adsc.202300535

Dual Ni/Organophotoredox Catalyzed Allylative Ring Opening Reaction of Oxabenzonorbornadienes and Analogs

Abdoul G. Diallo, Déborah Paris, Djiby Faye, Sylvain Gaillard, Mark Lautens and Jean-Luc Renaud

ACS Catal., 2022, 12, 3681
DOI: 10.1021/acscatal.2c00512

Photoexcitation of Distinct Divalent Palladium Complexes in Cross‐Coupling Amination Under Air

Rajesh Kancherla, Krishnamoorthy Muralirajan, Sayan Dutta, Kuntal Pal, Bo Li, Bholanath Maity, Luigi Cavallo and Magnus Rueping

Angew Chem Int Ed, 2024, 63
DOI: 10.1002/anie.202314508

Metal-Free C(sp3)–H Bond Arylation of 3-Methylindole Derivatives via 3-Indole Imine Methides

Jie Wang, Run Yu, Cuicui Nian, Maoyan Liao, Zhengyu Han, Jianwei Sun and Hai Huang

Org. Lett., 2023, 25, 8478
DOI: 10.1021/acs.orglett.3c03406

O-Methyl-N-nitroisourea as a NCO Surrogate in Cu-Catalyzed Alkane C–H Amidination. A Masked Isocyanate Strategy

Jonathan Lusseau, Frédéric Robert and Yannick Landais

ACS Catal., 2023, 13, 14257
DOI: 10.1021/acscatal.3c03293

The Role of Excited States of LNiII/III(Aryl)(Halide) Complexes in Ni–Halide Bond Homolysis in the Arylation of Csp3–H Bonds

Bholanath Maity, Thais R. Scott, Gautam D. Stroscio, Laura Gagliardi and Luigi Cavallo

ACS Catal., 2022, 12, 13215
DOI: 10.1021/acscatal.2c04284

Direct C(sp3)–H Arylation of Unprotected Benzyl Anilines and Alkylarenes by Organocatalysis under Visible Light

Cheng Huang, Peng Xiao, Zhong-Ming Ye, Chen-Lu Wang, Chen Kang, Sheng Tang, Zhenhong Wei and Hu Cai

Org. Lett., 2024, 26, 304
DOI: 10.1021/acs.orglett.3c03980

Dual Nickel/Photoredox‐Catalyzed Site‐Selective Cross‐Coupling of 1,2‐Bis‐Boronic Esters Enabled by 1,2‐Boron Shifts

Hui Wang, Wangyujing Han, Adam Noble and Varinder K. Aggarwal

Angew Chem Int Ed, 2022, 61
DOI: 10.1002/anie.202207988

Selective Mono‐Defluorinative Cross‐Coupling of Trifluoromethyl arenes via Multiphoton Photoredox Catalysis

Jiaqi Jia, Serik Zhumagazy, Chen Zhu, Shao‐Chi Lee, Salman Alsharif, Huifeng Yue and Magnus Rueping

Chemistry A European J, 2024, 30
DOI: 10.1002/chem.202302927

Benzoyl cyanide, a general radical acylating reagent for photoredox-catalyzed benzylic site-selective acylation reactions

Zhaodong Zhu and Jingjing Wu

Sci. China Chem., 2024, 67, 3833
DOI: 10.1007/s11426-024-2309-5

Photoinduced Hydrogen Atom Transfer Activation of Benzylic C−H Bonds Functionalization

Guozhe Guo and Wenduo Li

Adv Synth Catal, 2025, 367
DOI: 10.1002/adsc.202401266

Group 14 Elements Hetero‐Difunctionalizations via Nickel‐Catalyzed Electroreductive Cross‐Coupling

Haifeng Chen, Chen Zhu, Huifeng Yue and Magnus Rueping

Angewandte Chemie, 2023, 135
DOI: 10.1002/ange.202306498

Selective Toluene Electrooxidation to Benzyl Alcohol

Madeleine K. Wilsey, Nathalia Cajiao, Aleksa Radovic, Michael L. Neidig, Yasemin Basdogan and Astrid M. Müller

J. Am. Chem. Soc., 2025, 147, 36117
DOI: 10.1021/jacs.5c05986

Characterization of A π–π stacking cocrystal of 4-nitrophthalonitrile directed toward application in photocatalysis

Ting Xue, Cheng Ma, Le Liu, Chunhui Xiao, Shao-Fei Ni and Rong Zeng

Nat Commun, 2024, 15
DOI: 10.1038/s41467-024-45686-1

Tuning the reactivity of benzylic radicals by virtue of the presence of an acid/ester functional group at the benzylic carbon

Upma Gulati, Anjali Gupta and Joydev K. Laha

Tetrahedron, 2026, 191, 135086
DOI: 10.1016/j.tet.2025.135086

General Modular and Convergent Approach to Diversely Functionalized Allylic Systems

Sachin Giri, Nikita Kvasovs and Vladimir Gevorgyan

J. Am. Chem. Soc., 2025, 147, 23545
DOI: 10.1021/jacs.5c02866

Photoredox catalysis enabling decarboxylative radical cyclization of γ,γ-dimethylallyltryptophan (DMAT) derivatives: formal synthesis of 6,7-secoagroclavine

Alessio Regni, Francesca Bartoccini and Giovanni Piersanti

Beilstein J. Org. Chem., 2023, 19, 918
DOI: 10.3762/bjoc.19.70

C–Centered Radicals: Generation, Detection, Stability and Perspectives

Archana Velloth, Piyush Kumar, Shabana Butt and Sugumar Venkataramani

Asian J Org Chem, 2025, 14
DOI: 10.1002/ajoc.202400686

Recyclable Mesoporous Graphitic Carbon Nitride Catalysts for the Sustainable Photoredox Catalyzed Synthesis of Carbonyl Compounds

Kathiravan Murugesan, Arunachalam Sagadevan, Lu Peng, Oleksandr Savateev and Magnus Rueping

ACS Catal., 2023, 13, 13414
DOI: 10.1021/acscatal.3c03798

Selective Alkylarylation Difunctionalization of 1,3-Butadienes via Nickel/Photoredox Dual Catalysis

Aidana Gimnkhan, Rajesh Kancherla, Krishnamoorthy Muralirajan and Magnus Rueping

Org. Lett., 2025, 27, 5509
DOI: 10.1021/acs.orglett.5c01518

Designed Iron Catalysts for Allylic C−H Functionalization of Propylene and Simple Olefins

Ruihan Wang, Yidong Wang, Ruiqi Ding, Parker B. Staub, Christopher Z. Zhao, Peng Liu and Yi‐Ming Wang

Angew Chem Int Ed, 2023, 62
DOI: 10.1002/anie.202216309

Nickel catalyzed multicomponent stereodivergent synthesis of olefins enabled by electrochemistry, photocatalysis and photo-electrochemistry

Chen Zhu, Huifeng Yue and Magnus Rueping

Nat Commun, 2022, 13
DOI: 10.1038/s41467-022-30985-2

Chemoselective Cleavage and Transamidation of Tertiary p-Methoxybenzyl Amides under Metal-Free Photoredox Catalysis

Hee-Chan Jeong, Hyo-Jun Lee and Keiji Maruoka

Org. Lett., 2024, 26, 9513
DOI: 10.1021/acs.orglett.4c03485

General Light-Induced Pd-Catalyzed Allylic C–H Alkylation of Internal Alkenes: Direct Access to Tertiary and Quaternary Carbon Centers

Subham Pradhan, Gaurav Prakash and Vladimir Gevorgyan

J. Am. Chem. Soc., 2025, 147, 43213
DOI: 10.1021/jacs.5c15245