Vinyl radicals in transition metal-catalyzed organic transformations

Mu-Han Li, Xiao-Rong Shu, Yue-Jiao Lu, Wen-Chan Tian, Yu He, Qiang Li, Zheng-Jun Wang, Guo-Ping Ge and Wen-Ting Wei

Org. Chem. Front., 2024, 11, 5202
DOI: 10.1039/D4QO00995A

Copper-catalyzed anti-stereoselective 1,2-silylamination of alkynes

Kelu Yan, Xiaoyu Wang, Jiangwei Wen, Qiuyun Li, Jianjing Yang, Xinru Tao, Shenghao Pan, Haosheng Liang and Xiu Wang

Org. Chem. Front., 2025, 12, 3870
DOI: 10.1039/D5QO00040H

Recent progress in the organoselenium-catalyzed difunctionalization of alkenes

Pei Qu and Gong-Qing Liu

Org. Biomol. Chem., 2025, 23, 1552
DOI: 10.1039/D4OB01553C

Recent advances in visible-light-mediated functionalization of olefins and alkynes using copper catalysts

Arti Ramani, Bhargav Desai, Bharatkumar Z. Dholakiya and Togati Naveen

Chem. Commun., 2022, 58, 7850
DOI: 10.1039/D2CC01611G

Copper-catalyzed regioselective 1,4-sulfonylcyanation of 1,3-enynes with sulfonyl chlorides and TMSCN

Yunhe Lv, Wanru Han, Weiya Pu, Jinhui Xie, Axue Wang, Mengyue Zhang, Jin Wang and Junrong Lai

Org. Chem. Front., 2022, 9, 3775
DOI: 10.1039/D2QO00486K

KBr-enabled electrochemical transformation of alkynes into α-bromoketones/1,2-diketones

Yulin Li, Siyu Lei and Yuexia Zhang

Org. Biomol. Chem., 2026, 24, 3421
DOI: 10.1039/D6OB00329J

Photocatalytic Markovnikov-type addition and cyclization of terminal alkynes leading to 4-sulfonyl quinoline-2(1H)-ones

Yu-Lin Zhai, Hui Zhou, Qing-Quan Liu, Bo-Rong Leng, Zixian Zhang, Jia-Zhuo Li, De-Cai Wang and Yi-Long Zhu

Chem. Commun., 2022, 58, 5112
DOI: 10.1039/D2CC01169G

Non-decarboxylative functionalization of free carboxylic acids: strategies for C–O bond formation via photo- and electrochemical approaches

Binbin Huang

Green Chem., 2026, 28, 7586
DOI: 10.1039/D6GC00661B

Visible light-mediated synthesis of α-alkoxy/hydroxy diarylacetaldehydes from terminal alkynes

Jaswant Kumar, Ajaz Ahmed, Sourav Kumar, Shabnam Raheem, Masood Ahmad Rizvi and Bhahwal Ali Shah

New J. Chem., 2022, 46, 10967
DOI: 10.1039/D2NJ01614A

Synthesis of 1,2-oxazetidines with a free –NH group via photoredox catalysis

Majid Ahmad Ganie, Muneer-Ul-Shafi Bhat, Masood Ahmad Rizvi, Shabnam Raheem and Bhahwal Ali Shah

Chem. Commun., 2022, 58, 8508
DOI: 10.1039/D2CC02892A

Micro-photo-flow reactor system for fused N-heteroaryl scaffold synthesis and late-stage functionalization of pyrazolopyridines

Sanjeev Kumar and Ajay K. Singh

Chem. Commun., 2022, 58, 11268
DOI: 10.1039/D2CC03713K

Photoinduced selective perfluoroalkylation of terminal alkynes via electron donor–acceptor complexes

Xiaolin Shi, Bo Yu, Xin Zhou and Yong Yang

Chem. Commun., 2024, 60, 2532
DOI: 10.1039/D4CC00105B

Coordinating activation strategy enables 1,2-alkylamidation of alkynes

Jing Ren, Junhua Xu, Xiangxiang Kong, Jinlong Li and Kaizhi Li

Chem. Sci., 2023, 14, 11466
DOI: 10.1039/D3SC03786J

Synthesis of phenolic derivatives via photoredox formal [4 + 2] tandem annulation of α-bromoketones and terminal alkynes

Yingchun Ma, Ping Yu, Guobao Shang, Jingqi Hu, Zilong Zhang, Lou Shi, Qiaowen Chang, Shaoguang Sun and Deqiang Liang

Org. Biomol. Chem., 2025, 23, 10857
DOI: 10.1039/D5OB01596K

Copper-catalyzed stereo- and regio-selective decarbonylative alkylation and sequential amination of alkynes with aldehydes and amides

Kelu Yan, Xiaoyu Wang, Jiangwei Wen, Jianjing Yang, Yuanyuan Zhang, Bingxin Zhou and Daoshan Yang

Org. Chem. Front., 2026, 13, 540
DOI: 10.1039/D5QO01356A

Electron-donor–acceptor (EDA) complex-driven regioselective vicinal and oxidative geminal functionalization of alkynes

Dinabandhu Barik, Nikita Chakraborty, Ashish K. Sahoo, Hirendra Nath Dhara and Bhisma K. Patel

Chem. Commun., 2024, 60, 12577
DOI: 10.1039/D4CC04610B

Highly selective catalyst- and additive-free iodosulfonylation of cyclopropenes in water

Chuxiong Peng, Fengyan Gu, Xiaofeng Lin, Ning Ding, Qichen Zhan, Peng Cao and Tao Cao

Green Chem., 2023, 25, 671
DOI: 10.1039/D2GC04296G

Modular access to sulfur substituted analogues of isocytosine via photoredox catalysis

Faheem Fayaz, Majid Ahmad Ganie, Sourav Kumar, Shabnam Raheem, Masood Ahmad Rizvi and Bhahwal Ali Shah

Chem. Commun., 2024, 60, 8256
DOI: 10.1039/D4CC02076F

Azofuran activation for annulative rearrangement enabled by gold(i)/Brønsted acid relay catalysis

Qian Rao, Yin Zhang, Yin-Ping Liu, Bo Jiang, Xiang Wang, Shu-Jiang Tu and Wen-Juan Hao

Chem. Commun., 2023, 59, 5725
DOI: 10.1039/D3CC00531C

Azido-alkynylation of alkenes through radical-polar crossover

Julien Borrel and Jerome Waser

Chem. Sci., 2023, 14, 9452
DOI: 10.1039/D3SC03309K

Three-component copper-catalyzed difluoroalkylamidation of alkynes: an efficient approach to difluoroalkylated enamides

Jing Ren, Kaiyun Liu, Jinlong Li, Xinyu Long and Kaizhi Li

Org. Chem. Front., 2025, 12, 5752
DOI: 10.1039/D5QO00751H

The stereo-divergent functionalization of alkynes: a comprehensive review

Ranjay Shaw, Ashmita Singh, Ismail Althagafi, Ramendra Pratap and Dharmendra Kumar Yadav

RSC Adv., 2025, 15, 12202
DOI: 10.1039/D5RA01579K

Photoredox‐ and Nickel‐Catalyzed Hydroalkylation of Alkynes with 4‐Alkyl‐1,4‐dihydropyridines: Ligand‐Controlled Regioselectivity

Yulin Zhang, Yoshiaki Tanabe, Shogo Kuriyama and Yoshiaki Nishibayashi

Chemistry A European J, 2022, 28
DOI: 10.1002/chem.202200727

Divergent Functionalization of Alkynes Enabled by Organic Photoredox Catalysis

Zhengbo Zhu, Siran Qian and David A. Nicewicz

Synlett, 2023, 34, 1023
DOI: 10.1055/a-2009-8279

Metal‐Free Tunable 1,2‐Difunctionalization of Terminal Alkynes: Synthesis of β‐Substituted α,β‐Unsaturated Ketones

Muneer‐Ul‐Shafi Bhat, Majid Ahmad Ganie and Bhahwal Ali Shah

Chemistry A European J, 2023, 29
DOI: 10.1002/chem.202302294

Synthesis of Isoquinolines and Related Heterocycles under Visible-Light Conditions

Yurong Yuan, Clara Faure, Doriane Menigaux, Mathieu Berthelot, Philippe Belmont and Etienne Brachet

J. Org. Chem., 2023, 88, 15750
DOI: 10.1021/acs.joc.3c01782

Recent Advances in Visible Light Induced Radical 1,2-Functionalization of Alkynes

Kangkui Li, Xianyang Long, Yue Huang and Shifa Zhu

Acta Chimica Sinica, 2024, 82, 658
DOI: 10.6023/A24030090

Photocatalytic vinyl radical-mediated multicomponent 1,4-/1,8-carboimination across alkynes and olefins/(hetero)arenes

Shan-Shan Li, Yu-Shi Jiang, Xue-Ling Luo, Xuming Ran, Yuqiang Li, Dong Wu, Cheng-Xue Pan and Peng-Ju Xia

Sci. China Chem., 2024, 67, 558
DOI: 10.1007/s11426-023-1812-x

Photocatalytic annulative trifluoromethyletherification of 1,6-enynes for accessing 1-indanones

Tian-Shu Zhang, Si-Qing Song, Meng-Jiao Qi, Wen-Juan Hao and Bo Jiang

Tetrahedron Letters, 2023, 114, 154290
DOI: 10.1016/j.tetlet.2022.154290

Thiol-Catalyzed Photodriven Stereoselective Hydrodifluoroacetylative Cyclization of Alkyne

Guangzhu Wang, Chaoren Shen and Kaiwu Dong

Org. Lett., 2023, 25, 2878
DOI: 10.1021/acs.orglett.3c00865

HFIP‐Triggered Reduction Radical Coupling of Enamides with Alkynes Towards β‐Keto Alkylamides via H‐Bonding Electron Transfer

Xingda Cheng, LuLu Zhao, Kelu Yan, Jianjing Yang, Lirong Xu and Jiangwei Wen

ChemCatChem, 2024, 16
DOI: 10.1002/cctc.202400737

Photoredox Catalyzed Thioformylation of Terminal Alkynes Using Nitromethane as a Formyl Source

Muneer-ul-Shafi Bhat, Majid Ahmad Ganie, Masood Ahmad Rizvi, Shabnam Raheem and Bhahwal Ali Shah

Org. Lett., 2022, 24, 6658
DOI: 10.1021/acs.orglett.2c02695

Atomically precise Cu32 nanoclusters with selenide doping: Synthesis, bonding, and catalysis

Rong Huo, Rui Ren, Lin Wang, Qinghua Xu, Bingzheng Yan, Jiangwei Zhang, Qingxiang Guo, Zongjie Guan, Hui Shen and Nanfeng Zheng

Aggregate, 2025, 6
DOI: 10.1002/agt2.679

Photoredox Mediated Synthesis of Substituted Imidazoles from Terminal Alkynes

Jaswant Kumar, Sourav Kumar, Syed Mohib Ali, Masood Ahmad Rizvi and Bhahwal Ali Shah

Chemistry A European J, 2025, 31
DOI: 10.1002/chem.202501097

Photoredox-Promoted Selective Synthesis of C-5 Thiolated 2-Aminothiazoles from Terminal Alkynes

Majid Ahmad Ganie, Muneer-ul-Shafi Bhat, Masood Ahmad Rizvi, Shabnam Raheem and Bhahwal Ali Shah

Org. Lett., 2022, 24, 7757
DOI: 10.1021/acs.orglett.2c03064

Efficient and regioselective C=S bond difunctionalization through a three-component radical relay strategy

Shan-Shan Li, Juan Luo, Shu-Nuo Liang, Dan-Na Chen, Li-Ning Chen, Cheng-Xue Pan and Peng-Ju Xia

Chinese Chemical Letters, 2025, 36, 110424
DOI: 10.1016/j.cclet.2024.110424

Catalyst‐Free Regio‐ and Stereoselective Alkenyltrifluoromethylation of Alkynes under Visible Light Irradiation

Lin Tang, Fengjuan Jia, Lufang Zhang, Donghui Ding, Yadan Liu, Ruijun Yu, Qing Gao, Yanping Zhang and Qiuju Zhou

Asian J Org Chem, 2025, 14
DOI: 10.1002/ajoc.202400715

Visible-Light-Promoted Oxidative Annulation of Naphthols and Alkynes: Synthesis of Functionalized Naphthofurans

Neha Chalotra, Iftkhar Hussain Shah, Shabnam Raheem, Masood Ahmad Rizvi and Bhahwal Ali Shah

J. Org. Chem., 2021, 86, 16770
DOI: 10.1021/acs.joc.1c01992

Visible-Light-Mediated Synthesis of N-Acyl-N,O-hemiacetals from Terminal Alkynes: Access to N,N-, N,S-, and N,O-Acetals

Majid Ahmad Ganie, Faheem Fayaz, Muneer-ul-Shafi Bhat, Masood Ahmad Rizvi, Shabnam Raheem and Bhahwal Ali Shah

Org. Lett., 2023, 25, 8234
DOI: 10.1021/acs.orglett.3c03263

A General Medium-to-Large Sized Ring Synthesis Enabled by Copper-Catalyzed Difluoroalkylamidation Cyclization of Alkynes

Jing Ren, Linfeng He, Jinlong Li, Ning Wang, Xinyu Long, Jiayin Yang and Kaizhi Li

Org. Lett., 2025, 27, 5253
DOI: 10.1021/acs.orglett.5c01459

Copper-Catalyzed Vicinal Thiocyanosulfonylation of Alkenes and Alkynes

Meng-Fan Duan, Mei Xiao, Olukayode Olamiji Ogundipe, Xin-Xin Wu and Jian-Ping Zou

J. Org. Chem., 2024, 89, 11558
DOI: 10.1021/acs.joc.4c01241

Phosphinothio(seleno)ation of alkynes/olefins and application on the late-stage functionalization of natural products

Chang-Wei Shao, Pei-Feng Wan, Quan Xu, Ze-Nan Yang, Mei-Yu Geng, Yu Zhang, Xing-Hua Zhang and Xu-Wen Li

Commun Chem, 2024, 7
DOI: 10.1038/s42004-024-01326-9

Sulfonium Salt-Mediated Dithiocarbamation of Terminal Alkynes with CS2 and Amines for Access to Z-Bis(dialkylaminethiocarbonyl) Alkenes

Li Yang, Si−si Chen, Jia Shu, Wei Huang, Sha Peng and Long-Yong Xie

J. Org. Chem., 2026, 91, 7640
DOI: 10.1021/acs.joc.5c03112

Synthesis of (E)‐β‐Iodovinyl Sulfones via Photoredox Catalyzed Difunctionalization of Terminal Alkynes

Sourav Kumar, Jaswant Kumar, Tahira Naqvi, Shabnam Raheem, Masood Ahmad Rizvi and Bhahwal Ali Shah

ChemPhotoChem, 2022, 6
DOI: 10.1002/cptc.202200110

Tolane‐Based Phosphino‐ and Arsino‐Ruthenium Complexes in Three Different Oxidation States: Ru(I), Ru(II) and Ru(III)

Benjamin Rudin, Carolin A. M. Stein and Joachim Ballmann

Chemistry A European J, 2025, 31
DOI: 10.1002/chem.202404546

Intra- and Intermolecular Cation–π Interactions between Onium Salts and Alkynes/Acetylene: Experimental and Theoretical Insights

Catherine Fressigné, Alexandre Jean, Morgane Sanselme, Jérôme Blanchet, Jacques Rouden, Jacques Maddaluno and Michaël De Paolis

J. Org. Chem., 2023, 88, 14494
DOI: 10.1021/acs.joc.3c01514

Copper-Catalyzed Asymmetric Functionalization of Vinyl Radicals for the Access to Vinylarene Atropisomers

Liang Fu, Xin Chen, Wenzheng Fan, Pinhong Chen and Guosheng Liu

J. Am. Chem. Soc., 2023, 145, 13476
DOI: 10.1021/jacs.3c04498

Three‐Component 1,2‐Methylamidation of Alkynes via Coordinating Activation Strategy

Jing Ren, Kaiyun Liu, Ning Wang, Jinlong Li, Xinyu Long, Chengming Li and Kaizhi Li

ChemistryOpen, 2025, 14
DOI: 10.1002/open.202500151

Reactivity of alkynyl selenides and tellurides derivatives: a review

Liane K. Soares, Sabrina S. Ferreira, Kethelyn M. da Rosa, Gabriel P. da Costa, Eder J. Lenardão and Angelita M. Barcellos

Phosphorus, Sulfur, and Silicon and the Related Elements, 2026, 1
DOI: 10.1080/10426507.2026.2620649

Recent Advances in the Application of Carbon Dioxide Radical Anion

Jing Hou, Yan Huang, Hao Li, Yuancui Wan, Yu Shao, Lewu Zhan, Dinghai Wang and Bindong Li

Chinese Journal of Organic Chemistry, 2024, 44, 3117
DOI: 10.6023/cjoc202404039

Active Site Motifs in Atom‐Precise Coinage‐Metal Nanoclusters for Diverse Chemical Bond Construction

Shu‐Zhen Luo, Guang‐Lei Dong, Bao‐Liang Han, Mateen Ahmad, Geng‐Geng Luo, Ming‐Yang Cao and Di Sun

Adv Funct Materials, 2026
DOI: 10.1002/adfm.76396

Photocatalytic Decarboxylative Hydroalkylation of Alkynes and Alkenes

Pengjie Yao, Taixian Lin, Jie Li, Ruifeng Fan, Long Sun, Jian-Jun Liu, Kangkui Li, Jingchao Chen and Baomin Fan

Org. Lett., 2025, 27, 13839
DOI: 10.1021/acs.orglett.5c04364

Exploring the Divergent Reactivity of Vinyl Radicals Emanating from Alkynes and Thiols via Photoredox Catalysis

Sourav Kumar and Bhahwal Ali Shah

Chemistry An Asian Journal, 2023, 18
DOI: 10.1002/asia.202300693

Recent Advances in Cyclization Reactions of 1,5-Enynones and 1,6-Enynones

Saideh Rajai-Daryasarei, Vaezeh Fathi Vavsari, Elmira Jamshidi and Saeed Balalaie

Synlett, 2026, 37, 945
DOI: 10.1055/a-2752-7839

Photoinduced NiH Catalysis with Trialkylamines for the Stereodivergent Transfer Semi‐Hydrogenation of Alkynes

Tingjun Hu, Mohammad Jaber, Gaël Tran, Didier Bouyssi, Nuno Monteiro and Abderrahmane Amgoune

Chemistry A European J, 2023, 29
DOI: 10.1002/chem.202301636

Rh(II)/Pd(0) Dual-Catalyzed Regio-Divergent Three-Component Propargylic Substitution

Jie Xu, Zhaoliang Ge, Kuiling Ding and Xiaoming Wang

JACS Au, 2023, 3, 2862
DOI: 10.1021/jacsau.3c00415

Enantioselective construction of C-B axially chiral alkenylborons by nickel-catalyzed radical relayed reductive coupling

Weihua Qiu, Rencai Tao, Yong He, Yao Zhou, Kai Yang and Qiuling Song

Nat Commun, 2024, 15
DOI: 10.1038/s41467-024-54597-0

Ir-enabled reductive hydroamination of alkynes with nitroarenes

Chengxiu Liu, Jiaxin Liang, Zhejun Ni, Jianhua Liao, Renshi Luo and Lu Ouyang

Journal of Catalysis, 2025, 452, 116453
DOI: 10.1016/j.jcat.2025.116453

Harnessing Functionalized Alkynes in Annulation Reactions: A Comprehensive Review

Nandini B. Kale, Mary Sravani Galla and Nagula Shankaraiah

Asian J Org Chem, 2026, 15
DOI: 10.1002/ajoc.70290

Visible-Light-Mediated Synthesis of Thioesters Using Thiocarboxylic Acid as the Dual Reagent

Muneer-ul-Shafi Bhat, Majid Ahmad Ganie, Sourav Kumar, Masood Ahmad Rizvi, Shabnam Raheem and Bhahwal Ali Shah

J. Org. Chem., 2024, 89, 4607
DOI: 10.1021/acs.joc.3c02877

Visible‐Light‐Mediated [2+2] Photocycloadditions of Alkynes

Qing‐Bao Zhang, Feng Li, Bin Pan, Lei Yu and Xiang‐Guo Yue

Chemistry A European J, 2024, 30
DOI: 10.1002/chem.202401501

ICl-Mediated Functional Group Interconversion from Methyl Homopropargyl Ether to α-Iodo-γ-chloroketone

Yu Chen, Samual Hee, Xiaochen Liu, Sajal Das, Dongsub Hong, Pak-Hing Leung, Yongxin Li, Jiaming Li and Jianbo Liu

J. Org. Chem., 2022, 87, 15129
DOI: 10.1021/acs.joc.2c01638

Energy Transfer (EnT)-Mediated Stereoselective Aryl-Heterofunctionalization of Unactivated Alkynes via Radical Rearrangement

Xin-Chao Meng, Tian-Xiong Pan, Feng Yang, Hai-Xi Zhu, Yu-Wen Huang, Bo-Rong Leng, De-Cai Wang and Yi-Long Zhu

J. Org. Chem., 2025, 90, 1061
DOI: 10.1021/acs.joc.4c02462

Visible‐Light‐Mediated Synthesis of α‐Halomethyl Ketones from Terminal Alkynes

Iftkhar Hussain Shah, Sourav Kumar, Jaswant Kumar, Shabnam Raheem, Masood Ahmad Rizvi and Bhahwal Ali Shah

ChemPhotoChem, 2022, 6
DOI: 10.1002/cptc.202100231

Copper‐Catalyzed Three‐Component Silylamidation of Terminal Alkynes

Jing Ren, Xiangxiang Kong, Ning Wang, Jinlong Li, Xinyu Long and Kaizhi Li

Adv Synth Catal, 2025, 367
DOI: 10.1002/adsc.70028

Photoredox catalytic alkylarylation of alkynes with arylsulfonylacetate as bifunctional reagent

Chonglong He, Min Wang, Yulong Wang, Lirong Zhao, Youkang Zhou, Keyuan Zhang, Shenyu Shen, Yaqiong Su, Xin-Hua Duan and Le Liu

Sci. China Chem., 2024, 67, 2022
DOI: 10.1007/s11426-023-1930-6

Copper-Catalyzed 1,2-Difunctionalization Trifluoromethylamidation of Alkynes Assisted by a Coordinating Group

Jing Ren, Kaiyun Liu, Ning Wang, Xiangxiang Kong, Jinlong Li and Kaizhi Li

ACS Catal., 2023, 13, 11001
DOI: 10.1021/acscatal.3c02662

Sulfonium Salt-Mediated Regio- and Stereoselective Aminosulfonylation of Alkynes with Sulfinates and Azoles

Sha Peng, Jia-Xin Huang, Le Jiang, Li-Hua Yang and Long-Yong Xie

Org. Lett., 2026, 28, 4378
DOI: 10.1021/acs.orglett.6c00448

Synthesis of β‐Alkylated Enamides by Copper‐Catalyzed Anti‐Stereoselective and β‐Regioselective 1,2‐Alkylamination of Alkynes

Xiaoyu Wang, Kelu Yan, Jiangwei Wen, Qiuyun Li, Yuhang Sun, Mingyu Zhao and Jianjing Yang

Adv Synth Catal, 2026, 368
DOI: 10.1002/adsc.70262