Chemoselective C(α)–C(β) bond cleavage of saturated aryl ketones with amines leading to α-ketoamides: a copper-catalyzed aerobic oxidation process with air

Chengkou Liu, Zhao Yang, Yu Zeng, Zheng Fang and Kai Guo

Org. Chem. Front., 2017, 4, 2375
DOI: 10.1039/C7QO00690J

Multicomponent reactions and photo/electrochemistry join forces: atom economy meets energy efficiency

Guglielmo A. Coppola, Serena Pillitteri, Erik V. Van der Eycken, Shu-Li You and Upendra K. Sharma

Chem. Soc. Rev., 2022, 51, 2313
DOI: 10.1039/D1CS00510C

Visible-light induced copper(i)-catalyzed oxidative cyclization of o-aminobenzamides with methanol and ethanol via HAT

Mandapati Bhargava Reddy, Kesavan Prasanth and Ramasamy Anandhan

Org. Biomol. Chem., 2020, 18, 9601
DOI: 10.1039/D0OB02234A

Copper-catalyzed switchable cyclization of alkyne-tethered α-bromocarbonyls: selective access to quinolin-2-ones and quinoline-2,4-diones

Qing-Qing Kang, Zi-Ying Wang, Sen-Jie Hu, Chun-Mei Luo, Xue-Er Cai, Yong-Bin Sun, Ting Li and Wen-Ting Wei

Org. Chem. Front., 2022, 9, 6617
DOI: 10.1039/D2QO01240E

Photocatalytic functionalizations of alkynes

Neha Chalotra, Jaswant Kumar, Tahira Naqvi and Bhahwal Ali Shah

Chem. Commun., 2021, 57, 11285
DOI: 10.1039/D1CC04014F

Photocatalyzed oxidative cleavage of CC bond to carbonyl compounds by a recyclable homogeneous carbon nitride semiconductor/aqueous system

Rui Jia, Jingjing Wang, Yuqin Jiang, Bangqing Ni and Tengfei Niu

Org. Biomol. Chem., 2022, 20, 8305
DOI: 10.1039/D2OB01640K

Singlet oxygen mediated dual C–C and C–N bond cleavage in visible light

Ritu, Charu Sharma, Sharvan Kumar and Nidhi Jain

Org. Biomol. Chem., 2020, 18, 2921
DOI: 10.1039/D0OB00563K

Arylacetylenes as two-carbon synthons: synthesis of eight-membered rings via CC bond cleavage

Peng Zhao, Xiao-Xiao Yu, You Zhou, Chun Huang, Yan-Dong Wu, Yan-Ping Zhu and An-Xin Wu

Chem. Commun., 2020, 56, 12554
DOI: 10.1039/D0CC05363E

Visible-light-driven copper-catalyzed aerobic oxidative cascade cyclization of N-tosylhydrazones and terminal alkynes: regioselective synthesis of 3-arylcoumarins

Ayyakkannu Ragupathi, Arunachalam Sagadevan, Vaibhav Pramod Charpe, Chun-Cheng Lin, Jih-Ru Hwu and Kuo Chu Hwang

Chem. Commun., 2019, 55, 5151
DOI: 10.1039/C9CC01801H

Substituent-controlled selective synthesis of 1,2-diketones and internal alkynes from terminal alkynes and arylboronic acids via α-stilbene radicals obtained from heteroleptic Cu(i) complexes under visible light

Nalladhambi Neerathilingam, Kesavan Prasanth and Ramasamy Anandhan

Green Chem., 2022, 24, 8685
DOI: 10.1039/D2GC03011J

Singlet-oxygen-driven stereoselective iodothiocyanation and iodoselenocyanation of alkynes

Mahima Gupta, Ashwini Vishwasrao Katkar, Vaibhav Pramod Charpe and Kuo Chu Hwang

RSC Sustainability, 2026, 4, 760
DOI: 10.1039/D5SU00867K

Transformations of alkynes to carboxylic acids and their derivatives via CC bond cleavage

Shivalinga Kolle and Sanjay Batra

Org. Biomol. Chem., 2016, 14, 11048
DOI: 10.1039/C6OB01912A

Copper(ii)-mediated, carbon degradation-based amidation of phenylacetic acids toward N-substituted benzamides

Leiling Deng, Bin Huang and Yunyun Liu

Org. Biomol. Chem., 2018, 16, 1552
DOI: 10.1039/C8OB00064F

Visible light-mediated copper catalyzed regioselective diamination of terminal alkynes at room temperature: a facile synthesis of substituted imidazo[1,2-α]pyridines

Vaibhav Pramod Charpe, Mahima Gupta and Kuo Chu Hwang

Green Chem., 2024, 26, 1329
DOI: 10.1039/D3GC04062C

Visible-light induced copper(i)-catalysed denitrogenative oxidative coupling of hydrazinylpyridines with terminal alkynes

Vaibhav Pramod Charpe, Aniket A. Hande, Arunachalam Sagadevan and Kuo Chu Hwang

Green Chem., 2018, 20, 4859
DOI: 10.1039/C8GC01180J

Cleavage of carbon–carbon bonds by radical reactions

Paramasivam Sivaguru, Zikun Wang, Giuseppe Zanoni and Xihe Bi

Chem. Soc. Rev., 2019, 48, 2615
DOI: 10.1039/C8CS00386F

Visible-light initiated aerobic oxidations: a critical review

Xu Zhang, K. P. Rakesh, L. Ravindar and Hua-Li Qin

Green Chem., 2018, 20, 4790
DOI: 10.1039/C8GC02382D

C3N4-Photocatalyzed aerobic oxidative cleavage of CC bonds in alkynes with diazonium salts leading to two different aldehydes or esters in one pot

Jingjing Wang, Bangqing Ni, Tengfei Niu and Fei Ji

Catal. Sci. Technol., 2020, 10, 8458
DOI: 10.1039/D0CY01773F

Copper catalyzed photoredox synthesis of α-keto esters, quinoxaline, and naphthoquinone: controlled oxidation of terminal alkynes to glyoxals

Deb Kumar Das, V. Kishore Kumar Pampana and Kuo Chu Hwang

Chem. Sci., 2018, 9, 7318
DOI: 10.1039/C8SC03447H

Photoredox synthesis of functionalized quinazolines via copper-catalyzed aerobic oxidative Csp2–H annulation of amidines with terminal alkynes

Vaibhav Pramod Charpe, Ayyakkannu Ragupathi, Arunachalam Sagadevan and Kuo Chu Hwang

Green Chem., 2021, 23, 5024
DOI: 10.1039/D1GC01493E

Chemodivergent synthesis of N-(pyridin-2-yl)amides and 3-bromoimidazo[1,2-a]pyridines from α-bromoketones and 2-aminopyridines

Yanpeng Liu, Lixue Lu, Haipin Zhou, Feijie Xu, Cong Ma, Zhangjian Huang, Jinyi Xu and Shengtao Xu

RSC Adv., 2019, 9, 34671
DOI: 10.1039/C9RA06724H

Ce(iii)-catalyzed highly efficient synthesis of pyridyl benzamides from aminopyridines and nitroolefins without external oxidants

Zhengwang Chen, Xiaowei Wen, Yiping Qian, Pei Liang, Botao Liu and Min Ye

Org. Biomol. Chem., 2018, 16, 1247
DOI: 10.1039/C7OB03113K

Visible light-induced aerobic oxidation of diarylalkynes to α-diketones catalyzed by copper-superoxo at room temperature

Vaibhav Pramod Charpe, Arunachalam Sagadevan and Kuo Chu Hwang

Green Chem., 2020, 22, 4426
DOI: 10.1039/D0GC00975J

Copper-catalysed Csp3–Csp cross-couplings between cyclobutanone oxime esters and terminal alkynes induced by visible light

Binlin Zhao, Yixiao Wu, Yu Yuan and Zhuangzhi Shi

Chem. Commun., 2020, 56, 4676
DOI: 10.1039/D0CC00988A

Green and sustainable visible light-mediated formation of amide bonds: an emerging niche in organic chemistry

Jitender Singh and Anuj Sharma

New J. Chem., 2022, 46, 16220
DOI: 10.1039/D2NJ02406C

Singlet Oxygen-Mediated Regioselective Thiocyanation of Terminal Alkynes, Alkenes, Indoles, Pyrrole, Anilines, and Phenols

Mahima Gupta, Vaibhav Pramod Charpe and Kuo Chu Hwang

ACS Sustainable Chem. Eng., 2024, 12, 16297
DOI: 10.1021/acssuschemeng.4c05654

Thiosemicarbazone- and Thiourea-Functionalized Calix[4]arenes in cone and 1,3-alternate Conformations: Receptors for the Recognition of Ions

Andrés Ochoa, Belén Hernández-Arancibia, José Herrera-Muñoz, Horacio Gómez-Machuca and Claudio Saitz

Chemosensors, 2025, 13, 48
DOI: 10.3390/chemosensors13020048

Vanadium‐Catalyzed N‐Benzoylation of 2‐Aminopyridines via Oxidative C(CO)−C(CO) Bond Cleavage of 1,2‐Diketones, N→N′ Aroyl Migration and Hydrolysis of 2‐(Diaroylamino)pyridines

Chander Singh Digwal, Upasana Yadav, P. V. Sri Ramya, Baijayantimala Swain and Ahmed Kamal

Asian J Org Chem, 2018, 7, 865
DOI: 10.1002/ajoc.201800012

Metal-free photocatalyzed cross coupling of aryl (heteroaryl) bromides with isonitriles

Xiangguang Li, Deqiang Liang, Wenzhong Huang, Huanli Sun, Lvsu Wang, Mengran Ren, Baoling Wang and Yinhai Ma

Tetrahedron, 2017, 73, 7094
DOI: 10.1016/j.tet.2017.10.074

Employing Cu2O Particles for Oxidative Synthesis of Arylketones and Propargyl Amines under Visible Light

Mahima Gupta, Vaibhav Pramod Charpe, Ashwini Vishwasrao Katkar, Munusamy Shanmugam and Kuo Chu Hwang

ACS Sustainable Chem. Eng., 2025, 13, 15780
DOI: 10.1021/acssuschemeng.5c01308

Carbon-carbon triple bond cleavage and reconstitution to achieve aryl amidation using nitrous acid esters

Zi-Ying Wang, Shoujun Wang, Nan-Nan Dai, Yao Xiao, Yu Zhou, Wen-Chan Tian, Dongru Sun, Qiang Li, Yong Wang and Wen-Ting Wei

Nat Commun, 2025, 16
DOI: 10.1038/s41467-025-56370-3

Visible Light-Induced Excited-State Transition-Metal Catalysis

Rajesh Kancherla, Krishnamoorthy Muralirajan, Arunachalam Sagadevan and Magnus Rueping

Trends in Chemistry, 2019, 1, 510
DOI: 10.1016/j.trechm.2019.03.012

Visible Light‐Mediated Copper(I)‐Catalysed Aerobic Oxidation of Ynamides/Ynamines at Room Temperature: A Sustainable Approach to the Synthesis of α‐Ketoimides/α‐Ketoamides

Ayyakkannu Ragupathi, Vaibhav Pramod Charpe, Arunachalam Sagadevan and Kuo Chu Hwang

Adv Synth Catal, 2017, 359, 1138
DOI: 10.1002/adsc.201600925

Visible Light Induced Synthesis of 2-Benzoxazolecarboxamides Promoted by a Conjugated Microporous Polymer

Yujie Zhang, Rui Wang, Cuifen Lu, Chao Ma, Feiyi Wang, Guichun Yang, Yuexing Zhang and Junqi Nie

ACS Sustainable Chem. Eng., 2024, 12, 16239
DOI: 10.1021/acssuschemeng.4c05275

Recent Advancement in the Copper Mediated Synthesis of Heterocyclic Amides as Important Pharmaceutical and Agrochemicals

Prakash Chandra

ChemistrySelect, 2021, 6, 10274
DOI: 10.1002/slct.202103035

Visible‐Light‐Enabled Synthesis of Pyridyl Benzamides via Oxidative Decarbethoxylation using Copper(I) Iodide/Air at Room Temperature

Anup Kumar Sharma, Promod Kumar, Ramesh Kumar Vishwakarma and Krishna Nand Singh

Asian J Org Chem, 2019, 8, 873
DOI: 10.1002/ajoc.201900146

Decarboxylative Hydroalkylation of Alkynes via Dual Copper-Photoredox Catalysis

Marco M. Mastandrea, Santiago Cañellas, Xisco Caldentey and Miquel A. Pericàs

ACS Catal., 2020, 10, 6402
DOI: 10.1021/acscatal.0c01742

Visible Light Copper Photoredox-Catalyzed Aerobic Oxidative Coupling of Phenols and Terminal Alkynes: Regioselective Synthesis of Functionalized Ketones via C≡C Triple Bond Cleavage

Arunachalam Sagadevan, Vaibhav Pramod Charpe, Ayyakkannu Ragupathi and Kuo Chu Hwang

J. Am. Chem. Soc., 2017, 139, 2896
DOI: 10.1021/jacs.6b13113

Photocatalysis in Dual Catalysis Systems for Carbon‐Nitrogen Bond Formation

Swati Singh, Vishal Jyoti Roy, Neha Dagar, Partha Pratim Sen and Sudipta Raha Roy

Adv Synth Catal, 2021, 363, 937
DOI: 10.1002/adsc.202001176

A Chemoselective N-Arylation Reaction of 2-Aminopyridine Derivatives with Arynes

Bin Cheng, Jian Wei, Bing Zu, Jianfei Zhao, Taimin Wang, Xiaoguang Duan, Renqi Wang, Yun Li and Hongbin Zhai

J. Org. Chem., 2017, 82, 9410
DOI: 10.1021/acs.joc.7b01405

Photoredox Catalysis with Metal Complexes Made from Earth‐Abundant Elements

Christopher B. Larsen and Oliver S. Wenger

Chemistry A European J, 2018, 24, 2039
DOI: 10.1002/chem.201703602

Photoredox Oxo-C(sp3)–H Bond Functionalization via in Situ Cu(I)-Acetylide Catalysis

Zi-Qi Song, Zan Liu, Qi-Chao Gan, Tao Lei, Chen-Ho Tung and Li-Zhu Wu

Org. Lett., 2020, 22, 832
DOI: 10.1021/acs.orglett.9b04277

Developments in visible-light-mediated copper photocatalysis

Thomas P. Nicholls and Alex C. Bissember

Tetrahedron Letters, 2019, 60, 150883
DOI: 10.1016/j.tetlet.2019.06.042

Metal-mediated cleavage of unsaturated C-C bonds

Antony P.Y. Chan and Alexey G. Sergeev

Coordination Chemistry Reviews, 2020, 413, 213213
DOI: 10.1016/j.ccr.2020.213213

Copper(I)-catalysed aerobic oxidative selective cleavage of C C bond with DMAP: Facile access to N-substituted benzamides

Haojie Ma, Guoqiang Lu, Bo Han, Guosheng Huang, Yuqi Zhang and Ji-Jiang Wang

Tetrahedron Letters, 2021, 75, 153199
DOI: 10.1016/j.tetlet.2021.153199

Metal-Free Synthesis of N-(Pyridine-2-yl)amides from Ketones via Selective Oxidative Cleavage of C(O)–C(Alkyl) Bond in Water

Yanpeng Liu, Honghao Sun, Zhangjian Huang, Cong Ma, Aijun Lin, Hequan Yao, Jinyi Xu and Shengtao Xu

J. Org. Chem., 2018, 83, 14307
DOI: 10.1021/acs.joc.8b01956

Visible-light-mediated copper photocatalysis for organic syntheses

Yajing Zhang, Qian Wang, Zongsheng Yan, Donglai Ma and Yuguang Zheng

Beilstein J. Org. Chem., 2021, 17, 2520
DOI: 10.3762/bjoc.17.169

Metallaphotoredox: The Merger of Photoredox and Transition Metal Catalysis

Amy Y. Chan, Ian B. Perry, Noah B. Bissonnette, Benito F. Buksh, Grant A. Edwards, Lucas I. Frye, Olivia L. Garry, Marissa N. Lavagnino, Beryl X. Li, Yufan Liang, Edna Mao, Agustin Millet, James V. Oakley, Nicholas L. Reed, Holt A. Sakai, Ciaran P. Seath and David W. C. MacMillan

Chem. Rev., 2022, 122, 1485
DOI: 10.1021/acs.chemrev.1c00383

Copper’s rapid ascent in visible-light photoredox catalysis

Asik Hossain, Aditya Bhattacharyya and Oliver Reiser

Science, 2019, 364
DOI: 10.1126/science.aav9713

A concise review on copper catalyzed synthesis of α-ketoamides

Amit Gautam, Biswa Ranjan Swain, Sonali B. Jethy, V. Ravichandiran and Sharada Prasanna Swain

Applied Catalysis O: Open, 2025, 202, 207039
DOI: 10.1016/j.apcato.2025.207039

Visible Light-Induced Transition Metal Catalysis

Kelvin Pak Shing Cheung, Sumon Sarkar and Vladimir Gevorgyan

Chem. Rev., 2022, 122, 1543
DOI: 10.1021/acs.chemrev.1c00403

Recent Advances in the Functionalization of Hydrocarbons: Synthesis of Amides and its Derivatives

Thatikonda Narendar Reddy and Dênis Pires de Lima

Asian J Org Chem, 2019, 8, 1227
DOI: 10.1002/ajoc.201900317

Direct Transformation of Alkylarenes into N‐(Pyridine‐2‐yl)amides by C(sp3)–C(sp3) Bond Cleavage

Haipin Zhou, Yanpeng Liu, Haidong Xia, Jinyi Xu, Tingfang Wang and Shengtao Xu

Eur J Org Chem, 2020, 2020, 6468
DOI: 10.1002/ejoc.202001137

Applications of Photoredox Catalysis for the Radical-Induced Cleavage of C–C Bonds

Jaro Vanderghinste and Shoubhik Das

Synthesis, 2022, 54, 3383
DOI: 10.1055/a-1702-6193

The Synthesis of N-(Pyridin-2-yl)-Benzamides from Aminopyridine and Trans-Beta-Nitrostyrene by Fe2Ni-BDC Bimetallic Metal–Organic Frameworks

Trinh Duy Nguyen, Oanh Kim Thi Nguyen, Thuan Van Tran, Vinh Huu Nguyen, Long Giang Bach, Nhan Viet Tran, Dai-Viet N. Vo, Tuyen Van Nguyen, Seong-Soo Hong and Sy Trung Do

Processes, 2019, 7, 789
DOI: 10.3390/pr7110789

Convenient Access to C4‐Dicarbonylation of Anilines by Iodine‐Promoted Oxidative Cross‐Coupling Reactions

Panpan Wang, Yajie Fu, Ping Wu, Xin Guo and Baohua Chen

Asian J Org Chem, 2017, 6, 1398
DOI: 10.1002/ajoc.201700212

Copper‐Catalyzed Decarbonylative Synthesis of Pyridyl‐Substituted Ureas by the Reaction of 2‐Aminopyridines with N‐Arylmaleimides as N‐Arylcarbamoyl Surrogate

Abhinay Shukla, Shiv Chand, Saurabh Kumar and Krishna Nand Singh

Adv Synth Catal, 2026, 368
DOI: 10.1002/adsc.70225

Cobalt nanoparticles-catalyzed aerobic oxygenation and esterification of alkynes via C≡C bonds cleavage

Yujing Li, Huihui Luo, Shuo Wang, Lei Li, Guosong Li and Wen Dai

iScience, 2023, 26, 107608
DOI: 10.1016/j.isci.2023.107608

Recent Advances in Visible-Light-Mediated Amide Synthesis

Bin Lu, Wen-Jing Xiao and Jia-Rong Chen