Recent Advances in Pyridinium Salts as Radical Reservoirs in Organic Synthesis

Click to copy article linkArticle link copied!

This article is cited by 293 publications.

1. Vadla Shiva Prasad, Silari Mohana Krishna, Vadithya Ranga Rao, Dharavath Ravi, Chelukalapally Anil Kumar, Praveen Reddy Adiyala. Visible Light-Induced Alkylation of Malononitrile-Assisted Ketones through Deaminative Couplings. The Journal of Organic Chemistry 2025, 90 (18) , 6244-6250. https://doi.org/10.1021/acs.joc.5c00297
2. Ya-Qi Liu, Rui Yang, Hongfang Li, Teck-Peng Loh, Ming-Zhu Lu. Palladium-Catalyzed Hiyama Cross-Coupling of Heterocyclic Phosphonium Salts with Arylsilanes. Organic Letters 2025, 27 (16) , 4140-4145. https://doi.org/10.1021/acs.orglett.5c00709
3. Cristina Ascenzi Pettenuzzo, Deepak Ranjan Pradhan, Jujhar Singh, Lichuan Liu, Gabe Cuffel, Mathew J. Vetticatt, Yongming Deng. Photoredox/Pyridine N-Oxide Catalyzed Carbohydroxylation and Aminohydroxylation of α-Olefins. Journal of the American Chemical Society 2025, 147 (12) , 10382-10390. https://doi.org/10.1021/jacs.4c17657
4. Jiemin Ma, Yuhua Zhong, Hu Cai, Wentao Xu. Photocatalytic α-C(sp3)–H Arylation/Heteroarylation of Amines Enabled by Pyrylium Salt. The Journal of Organic Chemistry 2025, 90 (11) , 4080-4089. https://doi.org/10.1021/acs.joc.5c00090
5. Yifeng Kuang, Jiayi Shen, Kunjie Xu, Liangbin Huang. Ruthenium-Catalyzed meta-Alkylation of (Hetero)aromatic Acids with Pyridinium Salts Utilizing Ubiquitous Amines as Substrates. ACS Catalysis 2025, 15 (4) , 3162-3172. https://doi.org/10.1021/acscatal.4c07571
6. Hao Xu, Jia-Wen Jing, Yu-Bing Chen, Yong-Qing Xu, Xue-Qiang Chu, Xiaocong Zhou, Weidong Rao, Zhi-Liang Shen. Direct Cross-Couplings of Aryl Nonaflates with Aryl Bromides under Nickel Catalysis. The Journal of Organic Chemistry 2025, 90 (6) , 2341-2347. https://doi.org/10.1021/acs.joc.4c02777
7. Benjamin N. Ahern, Daniel J. Weix. One-Pot Chlorination and Cross-Electrophile Coupling of Alcohols with Aryl Chlorides. Organic Letters 2025, 27 (5) , 1164-1169. https://doi.org/10.1021/acs.orglett.4c04676
8. Lixian Shen, Jie Liu, Xue Peng, Zhengwen Lei, Zhen Wang, Yao-Fu Zeng. Photoredox-Catalyzed Three-Component Sulfonaminoalkynylation of Alkenes via a Radial/Polar Crossover. The Journal of Organic Chemistry 2025, 90 (4) , 1656-1662. https://doi.org/10.1021/acs.joc.4c02796
9. Shruti Rajput, Rajat, Nitesh, Priya Gupta, Harpal Singh, Nidhi Jain. Synthesis of Aminated C-3 Aryloylated Benzofuran, Furopyridine, Benzothiophene, and Indole Derivatives from 1,6-Enyne and N-Aminopyridinium Salt in Visible Light. The Journal of Organic Chemistry 2025, 90 (1) , 493-502. https://doi.org/10.1021/acs.joc.4c02439
10. Akash M. Sarkar, Benjamin Gossett, Michael T. Taylor. A Pyridinium Ylide-Alkylation Strategy for the Structural Diversification of N-Carbamoylpyridinium Salts. The Journal of Organic Chemistry 2024, 89 (23) , 17115-17121. https://doi.org/10.1021/acs.joc.4c01403
11. Promita Biswas, Asim Maity, Matthew T. Figgins, David C. Powers. Aziridine Group Transfer via Transient N-Aziridinyl Radicals. Journal of the American Chemical Society 2024, 146 (45) , 30796-30801. https://doi.org/10.1021/jacs.4c14169
12. Gan-Qi Qin, Jiao Wang, Xu-Rong Cao, Xue-Qiang Chu, Xiaocong Zhou, Weidong Rao, Li-Xin Zhai, Chengping Miao, Zhi-Liang Shen. Nickel-Catalyzed Reductive Amidation of Aryl Fluorosulfates with Isocyanates: Synthesis of Amides via C–O Bond Cleavage. The Journal of Organic Chemistry 2024, 89 (18) , 13735-13743. https://doi.org/10.1021/acs.joc.4c01399
13. Xuan-Bo Hu, Yuwei Chen, Chen-Long Zhu, Hao Xu, Xiaocong Zhou, Weidong Rao, Xiao-Chun Hang, Xue-Qiang Chu, Zhi-Liang Shen. Cross-Electrophile Couplings of Benzyl Sulfonium Salts with Thiosulfonates via C–S Bond Activation. The Journal of Organic Chemistry 2024, 89 (18) , 13601-13607. https://doi.org/10.1021/acs.joc.4c01786
14. Bo-Jie Huo, Wen-Wen Wang, Yi-Jie Huang, Xue-Qiang Chu, Hao Xu, Xiaocong Zhou, Weidong Rao, Zhi-Liang Shen. Sulfonylation of Pyridyl Phosphonium Salts with Sulfinate Salts in Aqueous Media for the Synthesis of 4-Pyridyl Sulfones via C–P Bond Cleavage. Organic Letters 2024, 26 (36) , 7763-7768. https://doi.org/10.1021/acs.orglett.4c02922
15. Krishna Prasad Gnyawali, Aldiyar Shakenov, Pandula T. Kirinde Arachchige, Chae S. Yi. Benzoquinone Ligand-Enabled Ruthenium-Catalyzed Deaminative Coupling of 2-Aminoaryl Aldehydes and Ketones with Branched Amines for Regioselective Synthesis of Quinoline Derivatives. The Journal of Organic Chemistry 2024, 89 (16) , 11119-11135. https://doi.org/10.1021/acs.joc.4c00063
16. Tian-Ci Wang, Zheng Zhang, Guodong Rao, Jiedong Li, Josephine Shirah, R. David Britt, Qilei Zhu, Yang Yang. Threonine Aldolase-Catalyzed Enantioselective α-Alkylation of Amino Acids through Unconventional Photoinduced Radical Initiation. Journal of the American Chemical Society 2024, 146 (32) , 22476-22484. https://doi.org/10.1021/jacs.4c05949
17. Masaaki Sakuma, Ryosuke Haraguchi. Charge-Enhanced Reactivity of Esters by a Cationic Substituent. Organic Letters 2024, 26 (29) , 6148-6152. https://doi.org/10.1021/acs.orglett.4c01962
18. Jingwei Liu, Jinyao Du, Lin-Bao Zhang, Ming Li, Weisi Guo. Electrochemical Benzylic C–H Amination via N-Aminopyridinium. The Journal of Organic Chemistry 2024, 89 (9) , 6465-6473. https://doi.org/10.1021/acs.joc.4c00502
19. Gyuri Han, Jihyun You, Junhyeon Choi, Eun Joo Kang. N-Iminopyridinium Compounds in Giese Reaction: Photoinduced Homolytic N–N and C–C Bond Cleavage for Cyanoalkyl Radical Generation. Organic Letters 2024, 26 (12) , 2414-2419. https://doi.org/10.1021/acs.orglett.4c00565
20. Yingjie Fan, Abigail L. Blenko, Steven Labalme, Wenbin Lin. Metal–Organic Layers with Photosensitizer and Pyridine Pairs Activate Alkyl Halides for Photocatalytic Heck-Type Coupling with Olefins. Journal of the American Chemical Society 2024, 146 (12) , 7936-7941. https://doi.org/10.1021/jacs.4c00258
21. Matthew C. Carson, Cindy R. Liu, Marisa C. Kozlowski. Synthesis of Phenol–Pyridinium Salts Enabled by Tandem Electron Donor–Acceptor Complexation and Iridium Photocatalysis. The Journal of Organic Chemistry 2024, 89 (5) , 3419-3429. https://doi.org/10.1021/acs.joc.3c02872
22. Liang-Feng Yang, Zhi-Qiang Xiong, Xuan-Hui Ouyang, Qiu-An Wang, Jin-Heng Li. Cobalt-Promoted Photoredox 1,2-Amidoamination of Alkenes with N-Sulfonamidopyridin-1-ium Salts and Free Amines. Organic Letters 2024, 26 (8) , 1667-1671. https://doi.org/10.1021/acs.orglett.4c00155
23. Chong-Hui Xu, Gui-Fen Lv, Jing-Hao Qin, Xin-Hua Xu, Jin-Heng Li. Visible-Light-Induced Photoredox 1,2-Dialkylation of Styrenes with α-Carbonyl Alkyl Bromides and Pyridin-1-ium Salts. The Journal of Organic Chemistry 2024, 89 (1) , 281-290. https://doi.org/10.1021/acs.joc.3c02018
24. Alexey A. Akulov, Mikhail V. Varaksin, Anna A. Nelyubina, Anton N. Tsmokaluk, Dmitrii G. Mazhukin, Alexsei Y. Tikhonov, Valery N. Charushin, Oleg N. Chupakhin. Iodine-Catalyzed Radical C–H Amination of Nonaromatic Imidazole Oxides: Access to Cyclic α-Aminonitrones. The Journal of Organic Chemistry 2024, 89 (1) , 463-473. https://doi.org/10.1021/acs.joc.3c02230
25. Zhiqi Liu, Yinghua Li, Weibin Fan, Deguang Huang. Iodine-Mediated Heterocyclization for the Synthesis of 6-Alkylthio-1,3,5-triazine-2,4-diamines from N-Alkylpyridinium Salts and NH4SCN. The Journal of Organic Chemistry 2024, 89 (1) , 676-680. https://doi.org/10.1021/acs.joc.3c02517
26. Son Hoai Doan, Binh Khanh Mai, Thanh Vinh Nguyen. Moisture-Assisted Hydroboration of Nitriles and Conversion Thereof to N-Heterocyles and N-Containing Derivatives. Organic Letters 2023, 25 (50) , 8981-8986. https://doi.org/10.1021/acs.orglett.3c03533
27. Chenyang Wang, Phong Dam, Mohamed Elghobashy, Angelika Brückner, Jabor Rabeah, Luis Miguel Azofra, Osama El-Sepelgy. Biomimetic Dehydroamination of Primary Amines. ACS Catalysis 2023, 13 (21) , 14205-14212. https://doi.org/10.1021/acscatal.3c04305
28. Yong-Chun Luo, Yang Wang, Run Shi, Xu-Gang Zhang, Huan-Huan Zhang, Peng-Fei Xu. Photoredox Catalyzed [3 + 2]-Annulation Reaction of Pyridinium 1,4-Zwitterionic Thiolates with Alkenes: Synthesis of Dihydrothiophenes. Organic Letters 2023, 25 (33) , 6105-6109. https://doi.org/10.1021/acs.orglett.3c02068
29. Girish Suresh Yedase, Munaifa Arif, Rositha Kuniyil, Veera Reddy Yatham. Photocatalytic Hydro Tri/Difluoromethylation of Alkenes with Bench Stable Tri/Difluoromethylating Reagents. Organic Letters 2023, 25 (33) , 6200-6205. https://doi.org/10.1021/acs.orglett.3c02413
30. Geun Seok Lee, Soon Hyeok Hong. Direct C(sp3)–H Acylation by Mechanistically Controlled Ni/Ir Photoredox Catalysis. Accounts of Chemical Research 2023, 56 (16) , 2170-2184. https://doi.org/10.1021/acs.accounts.3c00252
31. Jiantao Fu, Windsor Lundy, Rajdip Chowdhury, J. Cameron Twitty, Long P. Dinh, Jessica Sampson, Yu-hong Lam, Christo S. Sevov, Mary P. Watson, Dipannita Kalyani. Nickel-Catalyzed Electroreductive Coupling of Alkylpyridinium Salts and Aryl Halides. ACS Catalysis 2023, 13 (14) , 9336-9345. https://doi.org/10.1021/acscatal.3c01939
32. Xu-Ge Liu, Qian Yang, Deng-Yin Liu, Jing Liu, Dong-Hang Tan, Yu-Jun Ruan, Peng-Fei Wang, Xiao-Li Wang, Honggen Wang. Nickel-Catalyzed Reductive Decarboxylative/Deaminative Glycosylation of Activated Aliphatic Acids and Primary Amines. Organic Letters 2023, 25 (27) , 5022-5026. https://doi.org/10.1021/acs.orglett.3c01691
33. Nuwan Pannilawithana, Mina Son, Donghun Hwang, Mu-Hyun Baik, Chae S. Yi. Scope and Mechanistic Studies on the Ruthenium-Catalyzed Multicomponent Deaminative C–H Coupling Reaction of Phenols with Aldehydes and Enamines for the Formation of Xanthene and Dioxacyclic Derivatives. ACS Catalysis 2023, 13 (13) , 9051-9063. https://doi.org/10.1021/acscatal.3c01651
34. Dan Forster, Weisi Guo, Qian Wang, Jieping Zhu. Dual Photoredox and Copper Catalysis: Enantioselective 1,2-Amidocyanation of 1,3-Dienes. ACS Catalysis 2023, 13 (11) , 7523-7528. https://doi.org/10.1021/acscatal.3c01782
35. I. N. Chaithanya Kiran, Ramagonolla Kranthikumar. Nickel-Catalyzed Deaminative Ketone Synthesis: Coupling of Alkylpyridinium Salts with Thiopyridine Esters via C–N Bond Activation. Organic Letters 2023, 25 (20) , 3623-3627. https://doi.org/10.1021/acs.orglett.3c00943
36. James L. Douthwaite, Ruheng Zhao, Eunjae Shim, Babak Mahjour, Paul M. Zimmerman, Tim Cernak. Formal Cross-Coupling of Amines and Carboxylic Acids to Form sp3–sp2 Carbon–Carbon Bonds. Journal of the American Chemical Society 2023, 145 (20) , 10930-10937. https://doi.org/10.1021/jacs.2c11563
37. Peter Bellotti, Huan-Ming Huang, Teresa Faber, Frank Glorius. Photocatalytic Late-Stage C–H Functionalization. Chemical Reviews 2023, 123 (8) , 4237-4352. https://doi.org/10.1021/acs.chemrev.2c00478
38. Ganesh Chandra Upreti, Tavinder Singh, Kirti Khanna, Anand Singh. Pd-Catalyzed Photochemical Alkylative Functionalization of C═C and C═N Bonds. The Journal of Organic Chemistry 2023, 88 (7) , 4422-4433. https://doi.org/10.1021/acs.joc.2c03028
39. Juan Tang, Chaoqun Zhao, Shun Li, Jing Zhang, Xueli Zheng, Maolin Yuan, Haiyan Fu, Ruixiang Li, Hua Chen. Tandem Ring-Contraction/Regioselective C–H Iodination Reaction of Pyridinium Salts. The Journal of Organic Chemistry 2023, 88 (5) , 2809-2821. https://doi.org/10.1021/acs.joc.2c02472
40. Mrinmoy Das, Leila Zamani, Christopher Bratcher, Patricia Z. Musacchio. Azolation of Benzylic C–H Bonds via Photoredox-Catalyzed Carbocation Generation. Journal of the American Chemical Society 2023, 145 (7) , 3861-3868. https://doi.org/10.1021/jacs.2c12850
41. Changduo Pan, Zixian Yang, Xian Wu, Jin-Tao Yu, Chengjian Zhu. Substituent-Controlled Regioselective Photoinduced Cyclization of N-Allylbenzamides with N-Sulfonylaminopyridinium Salts. Organic Letters 2023, 25 (3) , 494-499. https://doi.org/10.1021/acs.orglett.2c04190
42. Li Xiong, Fengjuan Chen, Yihang Wu, Xinwei Hu, Zhixiong Ruan, Huanfeng Jiang, Wei Zeng. Cyclocarboamination of Alkynes with N-Aminopyridiniums by Photoredox Catalysis. Organic Letters 2022, 24 (42) , 7856-7860. https://doi.org/10.1021/acs.orglett.2c03336
43. Myojeong Kim, Yejin Koo, Sungwoo Hong. N-Functionalized Pyridinium Salts: A New Chapter for Site-Selective Pyridine C–H Functionalization via Radical-Based Processes under Visible Light Irradiation. Accounts of Chemical Research 2022, 55 (20) , 3043-3056. https://doi.org/10.1021/acs.accounts.2c00530
44. Long Huang, Rajesh Kancherla, Magnus Rueping. Nickel Catalyzed Regiodivergent Cross-Coupling Alkylation of Aryl Halides with Redox-Active Imines. ACS Catalysis 2022, 12 (19) , 11563-11572. https://doi.org/10.1021/acscatal.2c03396
45. Bin Wang, Cui-Tian Wang, Xue-Song Li, Xue-Yuan Liu, Yong-Min Liang. Visible-Light-Induced C–F and C–N Bond Cleavage for the Synthesis of gem-Difluoroalkenes. Organic Letters 2022, 24 (36) , 6566-6570. https://doi.org/10.1021/acs.orglett.2c02528
46. Wen-Xin Li, Bo-Wen Yang, Xuan Ying, Zhuo-Wen Zhang, Xue-Qiang Chu, Xiaocong Zhou, Mengtao Ma, Zhi-Liang Shen. Nickel-Catalyzed Direct Cross-Coupling of Diaryl Sulfoxide with Aryl Bromide. The Journal of Organic Chemistry 2022, 87 (17) , 11899-11908. https://doi.org/10.1021/acs.joc.2c01513
47. Yu-Zhao Wang, Peng-Yu Liang, Hong-Chao Liu, Wu-Jie Lin, Pan-Pan Zhou, Wei Yu. Visible-Light-Driven [3 + 2]/[4 + 2] Annulation Reactions of Alkenes with N-Aminopyridinium Salts. Organic Letters 2022, 24 (32) , 6037-6042. https://doi.org/10.1021/acs.orglett.2c02323
48. Xingjie Zhang, Chenchen Jiao, Di Qi, Xiaopan Liu, Zhiguo Zhang, Guisheng Zhang. Nickel-Catalyzed Deaminative Allenylation of Amino Acid Derivatives: Catalytic Activity Enhanced by an Amide-Type NN2 Pincer Ligand. Organic Letters 2022, 24 (29) , 5361-5365. https://doi.org/10.1021/acs.orglett.2c02042
49. Xin Li, Weili Si, Zhanhui Liu, Haitao Qian, Tingxue Wang, Shengnan Leng, Jinwei Sun, Yan Jiao, Xuan Zhang. Visible-Light-Promoted Desulfurative Alkylation of Alkyl Thianthrenium Salts with Activated Olefins. Organic Letters 2022, 24 (22) , 4070-4074. https://doi.org/10.1021/acs.orglett.2c01525
50. Kui Wang, Xiaoyu Liu, Siyu Yang, Yan Tian, Mingyang Zhou, Jianhua Zhou, Xiaofei Jia, Baoying Li, Siyuan Liu, Jianbin Chen. In Situ Alkyl Radical Recycling-Driven Decoupled Electrophotochemical Deamination. Organic Letters 2022, 24 (19) , 3471-3476. https://doi.org/10.1021/acs.orglett.2c01022
51. Fu-Sheng He, Ping Bao, Zhimei Tang, Feiyan Yu, Wei-Ping Deng, Jie Wu. Photoredox-Catalyzed α-Sulfonylation of Ketones from Sulfur Dioxide and Thianthrenium Salts. Organic Letters 2022, 24 (15) , 2955-2960. https://doi.org/10.1021/acs.orglett.2c01132
52. Caleb R. Hoopes, Francisco J. Garcia, Akash M. Sarkar, Nicholas J. Kuehl, David T. Barkan, Nicole L. Collins, Glenna E. Meister, Taylor R. Bramhall, Chien-Hsiang Hsu, Michael D. Jones, Markus Schirle, Michael T. Taylor. Donor–Acceptor Pyridinium Salts for Photo-Induced Electron-Transfer-Driven Modification of Tryptophan in Peptides, Proteins, and Proteomes Using Visible Light. Journal of the American Chemical Society 2022, 144 (14) , 6227-6236. https://doi.org/10.1021/jacs.1c10536
53. Jun Yang, Lina Yang, Jing Gu, Li Shuai, Hui Wang, Qin Ouyang, Yu-Long Li, Haibin Liu, Liang Gong. Nickel-Catalyzed Reductive Cascade Arylalkylation of Alkenes with Alkylpyridinium Salts. Organic Letters 2022, 24 (12) , 2376-2380. https://doi.org/10.1021/acs.orglett.2c00599
54. Tomoyuki Sekino, Shunta Sato, Tatsuhiko Yoshino, Masahiro Kojima, Shigeki Matsunaga. Regioselective Deaminative Allylation of Aliphatic Amines via Dual Cobalt and Organophotoredox Catalysis. Organic Letters 2022, 24 (11) , 2120-2124. https://doi.org/10.1021/acs.orglett.2c00319
55. Tomáš Neveselý, Max Wienhold, John J. Molloy, Ryan Gilmour. Advances in the E → Z Isomerization of Alkenes Using Small Molecule Photocatalysts. Chemical Reviews 2022, 122 (2) , 2650-2694. https://doi.org/10.1021/acs.chemrev.1c00324
56. Shang-Zheng Sun, Yue-Ming Cai, De-Liang Zhang, Jia-Bao Wang, Hong-Qing Yao, Xi-Yan Rui, Ruben Martin, Ming Shang. Enantioselective Deaminative Alkylation of Amino Acid Derivatives with Unactivated Olefins. Journal of the American Chemical Society 2022, 144 (3) , 1130-1137. https://doi.org/10.1021/jacs.1c12350
57. Yiting Gu, Hongfei Yin, Matthew Wakeling, Juzeng An, Ruben Martin. Defunctionalization of sp3 C–Heteroatom and sp3 C–C Bonds Enabled by Photoexcited Triplet Ketone Catalysts. ACS Catalysis 2022, 12 (2) , 1031-1036. https://doi.org/10.1021/acscatal.1c05329
58. Shuohan Ji, Shengxiang Qin, Chunyu Yin, Lu Luo, Hua Zhang. Unreactive C–N Bond Activation of Anilines via Photoinduced Aerobic Borylation. Organic Letters 2022, 24 (1) , 64-68. https://doi.org/10.1021/acs.orglett.1c03590
59. Shao-Chi Lee, Li-Yun Li, Zong-Nan Tsai, Yi-Hsin Lee, Yong-Ting Tsao, Pin-Gong Huang, Cheng-Ku Cheng, Heng-Bo Lin, Ting-Wei Chen, Chung-Hsin Yang, Cheng-Chau Chiu, Hsuan-Hung Liao. Aromatization as an Impetus to Harness Ketones for Metallaphotoredox-Catalyzed Benzoylation/Benzylation of (Hetero)arenes. Organic Letters 2022, 24 (1) , 85-89. https://doi.org/10.1021/acs.orglett.1c03672
60. Krishna Gnyawali, Pandula T. Kirinde Arachchige, Chae S. Yi. Synthesis of Flavanone and Quinazolinone Derivatives from the Ruthenium-Catalyzed Deaminative Coupling Reaction of 2′-Hydroxyaryl Ketones and 2-Aminobenzamides with Simple Amines. Organic Letters 2022, 24 (1) , 218-222. https://doi.org/10.1021/acs.orglett.1c03870
61. Jia-Xin Wang, Wei Ge, Wei-Long Xing, Ming-Chen Fu. Photoinduced Deaminative Alkylation for the Synthesis of γ-Ketoesters via Electron Donor–Acceptor Complex Formation. The Journal of Organic Chemistry 2021, 86 (24) , 18224-18231. https://doi.org/10.1021/acs.joc.1c02499
62. Branislav Ferko, Michaela Marčeková, Katarína Ráchel Detková, Jana Doháňošová, Dušan Berkeš, Pavol Jakubec. Visible-Light-Promoted Cross-Coupling of N-Alkylpyridinium Salts and Nitrostyrenes. Organic Letters 2021, 23 (22) , 8705-8710. https://doi.org/10.1021/acs.orglett.1c03122
63. Camille Banoun, Flavien Bourdreux, Emmanuel Magnier, Guillaume Dagousset. Intermolecular C–O Bond Formation with Alkoxyl Radicals: Photoredox-Catalyzed α-Alkoxylation of Carbonyl Compounds. Organic Letters 2021, 23 (22) , 8926-8930. https://doi.org/10.1021/acs.orglett.1c03444
64. Jonathan A. Andrews, Loïc R. E. Pantaine, Christopher F. Palmer, Darren L. Poole, Michael C. Willis. Sulfinates from Amines: A Radical Approach to Alkyl Sulfonyl Derivatives via Donor–Acceptor Activation of Pyridinium Salts. Organic Letters 2021, 23 (21) , 8488-8493. https://doi.org/10.1021/acs.orglett.1c03194
65. Olivia P. Bercher, Shane Plunkett, Thomas E. Mortimer, Mary P. Watson. Deaminative Reductive Methylation of Alkylpyridinium Salts. Organic Letters 2021, 23 (18) , 7059-7063. https://doi.org/10.1021/acs.orglett.1c02458
66. Dan Forster, Weisi Guo, Qian Wang, Jieping Zhu. Photoredox Catalytic Three-Component Amidoazidation of 1,3-Dienes. ACS Catalysis 2021, 11 (17) , 10871-10877. https://doi.org/10.1021/acscatal.1c03545
67. Jianyu Xu, J. Cameron Twitty, Mary P. Watson. Nickel-Catalyzed Deaminative Cyanation: Nitriles and One-Carbon Homologation from Alkyl Amines. Organic Letters 2021, 23 (16) , 6242-6245. https://doi.org/10.1021/acs.orglett.1c01959
68. Yu Lu, Chang-Zhen Fang, Qiang Liu, Bao-Lin Li, Zhi-Xiang Wang, Xiang-Yu Chen. Donor–Acceptor Complex Enables Cascade Radical Cyclization of N-Arylacrylamides with Katritzky Salts. Organic Letters 2021, 23 (14) , 5425-5429. https://doi.org/10.1021/acs.orglett.1c01758
69. José A. C. Delgado, José T. M. Correia, Emanuele F. Pissinati, Márcio W. Paixão. Biocompatible Photoinduced Alkylation of Dehydroalanine for the Synthesis of Unnatural α-Amino Acids. Organic Letters 2021, 23 (13) , 5251-5255. https://doi.org/10.1021/acs.orglett.1c01781
70. Chong-Hui Xu, Jin-Heng Li, Jian-Nan Xiang, Wei Deng. Merging Photoredox/Nickel Catalysis for Cross-Electrophile Coupling of Aziridines with Pyridin-1-ium Salts via Dearomatization. Organic Letters 2021, 23 (9) , 3696-3700. https://doi.org/10.1021/acs.orglett.1c01077
71. Chao-Shen Zhang, Lei Bao, Kun-Quan Chen, Zhi-Xiang Wang, Xiang-Yu Chen. Photoinduced α-Alkenylation of Katritzky Salts: Synthesis of β,γ-Unsaturated Esters. Organic Letters 2021, 23 (5) , 1577-1581. https://doi.org/10.1021/acs.orglett.0c04287
72. Benjamin Laroche, Xinjun Tang, Gaétan Archer, Riccardo Di Sanza, Paolo Melchiorre. Photochemical Chemoselective Alkylation of Tryptophan-Containing Peptides. Organic Letters 2021, 23 (2) , 285-289. https://doi.org/10.1021/acs.orglett.0c03735
73. Yao Ouyang, Chao-Lai Tong, Xiu-Hua Xu, Feng-Ling Qing. Copper and Zinc Copromoted Bromo(chloro)trifluoromethylation of Alkenes and Alkynes with Trifluoromethanesulfonic Anhydride. Organic Letters 2021, 23 (2) , 346-350. https://doi.org/10.1021/acs.orglett.0c03855
74. Xinwei He, Ruxue Li, Pui Ying Choy, Tianyi Liu, Junya Wang, On Ying Yuen, Man Pan Leung, Yongjia Shang, Fuk Yee Kwong. DMAP-Catalyzed Annulation Approach for Modular Assembly of Furan-Fused Chromenes. Organic Letters 2020, 22 (24) , 9444-9449. https://doi.org/10.1021/acs.orglett.0c03374
75. Shu-Zhen Lai, Yu-Ming Yang, Hai Xu, Zhen-Yu Tang, Zhuangzhu Luo. Photoinduced Deaminative Coupling of Alkylpyridium Salts with Terminal Arylalkynes. The Journal of Organic Chemistry 2020, 85 (23) , 15638-15644. https://doi.org/10.1021/acs.joc.0c01928
76. Limeng Zheng, Qinfang Jiang, Hanyang Bao, Bingwei Zhou, Shu-Ping Luo, Hongwei Jin, Huayue Wu, Yunkui Liu. Tertiary Amines Acting as Alkyl Radical Equivalents Enabled by a P/N Heteroleptic Cu(I) Photosensitizer. Organic Letters 2020, 22 (22) , 8888-8893. https://doi.org/10.1021/acs.orglett.0c03236
77. Fatima Rammal, Di Gao, Sondes Boujnah, Aqeel A. Hussein, Jacques Lalevée, Annie-Claude Gaumont, Fabrice Morlet-Savary, Sami Lakhdar. Photochemical C–H Silylation and Hydroxymethylation of Pyridines and Related Structures: Synthetic Scope and Mechanisms. ACS Catalysis 2020, 10 (22) , 13710-13717. https://doi.org/10.1021/acscatal.0c03726
78. Inwon Kim, Seongjin Park, Sungwoo Hong. Functionalization of Pyridinium Derivatives with 1,4-Dihydropyridines Enabled by Photoinduced Charge Transfer. Organic Letters 2020, 22 (21) , 8730-8734. https://doi.org/10.1021/acs.orglett.0c03347
79. Jacob M. Ganley, Philip R. D. Murray, Robert R. Knowles. Photocatalytic Generation of Aminium Radical Cations for C–N Bond Formation. ACS Catalysis 2020, 10 (20) , 11712-11738. https://doi.org/10.1021/acscatal.0c03567
80. Fatima Rammal, Di Gao, Sondes Boujnah, Annie−Claude Gaumont, Aqeel A. Hussein, Sami Lakhdar. Visible-Light-Mediated C–H Alkylation of Pyridine Derivatives. Organic Letters 2020, 22 (19) , 7671-7675. https://doi.org/10.1021/acs.orglett.0c02863
81. Heng Song, Ran Cheng, Qiao-Qiao Min, Xingang Zhang. Decarboxylative and Deaminative Alkylation of Difluoroenoxysilanes via Photoredox Catalysis: A General Method for Site-Selective Synthesis of Difluoroalkylated Alkanes. Organic Letters 2020, 22 (19) , 7747-7751. https://doi.org/10.1021/acs.orglett.0c02997
82. Xinwei He, Ruxue Li, Pui Ying Choy, Tianyi Liu, On Ying Yuen, Man Pan Leung, Yongjia Shang, Fuk Yee Kwong. Rapid Access of Alkynyl and Alkenyl Coumarins via a Dipyridinium Methylide and Propargylamine Cascade Reaction. Organic Letters 2020, 22 (18) , 7348-7352. https://doi.org/10.1021/acs.orglett.0c02674
83. Hanyang Bao, Bingwei Zhou, Shu-Ping Luo, Zheng Xu, Hongwei Jin, Yunkui Liu. P/N Heteroleptic Cu(I)-Photosensitizer-Catalyzed Deoxygenative Radical Alkylation of Aromatic Alkynes with Alkyl Aldehydes Using Dipropylamine as a Traceless Linker Agent. ACS Catalysis 2020, 10 (14) , 7563-7572. https://doi.org/10.1021/acscatal.0c02454
84. Sungwoo Jung, Sanghoon Shin, Seongjin Park, Sungwoo Hong. Visible-Light-Driven C4-Selective Alkylation of Pyridinium Derivatives with Alkyl Bromides. Journal of the American Chemical Society 2020, 142 (26) , 11370-11375. https://doi.org/10.1021/jacs.0c04499
85. Alya Inial, Fabrice Morlet-Savary, Jacques Lalevée, Annie−Claude Gaumont, Sami Lakhdar. Visible-Light-Mediated Access to Phosphate Esters. Organic Letters 2020, 22 (11) , 4404-4407. https://doi.org/10.1021/acs.orglett.0c01409
86. Maximilian Lübbesmeyer, Emily G. Mackay, Mark A. R. Raycroft, Jonas Elfert, Derek A. Pratt, Armido Studer. Base-Promoted C–C Bond Activation Enables Radical Allylation with Homoallylic Alcohols. Journal of the American Chemical Society 2020, 142 (5) , 2609-2616. https://doi.org/10.1021/jacs.9b12343
87. Namhoon Kim, Changseok Lee, Taehwan Kim, Sungwoo Hong. Visible-Light-Induced Remote C(sp3)–H Pyridylation of Sulfonamides and Carboxamides. Organic Letters 2019, 21 (23) , 9719-9723. https://doi.org/10.1021/acs.orglett.9b03879
88. Eugene S. Vasilyev, Ivan A. Trenikhin, Grigoriy A. Matrosov, Ekaterina A. Artyukha, Pavel A. Zaikin, Alexandr V. Mikheilis, Alexander M. Agafontsev, Tatyana V. Rybalova, Alexey V. Tkachev. Chiral quaternized nopinane-annelated 4,5-diazafluorenes: electrochemical and photochemical properties. Journal of Molecular Structure 2025, 1342 , 142718. https://doi.org/10.1016/j.molstruc.2025.142718
89. Efraín Polo-Cuadrado, Cristian Rojas-Peña, Karen Acosta-Quiroga, Lorena Camargo-Ayala, Yeray A. Rodríguez-Núñez, Edison Osorio, Jhon J. López, Rhonny Brid-Cuadrado, Margarita Gutierrez. Exploring pyridinium-based inhibitors of cholinesterases: A review of synthesis, efficacy, and structural insights. European Journal of Medicinal Chemistry Reports 2025, 14 , 100270. https://doi.org/10.1016/j.ejmcr.2025.100270
90. Qing‐Dong Wang, Xue Chen, Yuan‐Shuai Wu, Chengping Miao, Jin‐Ming Yang, Zhi‐Liang Shen. Palladium–Catalyzed α‐Arylation of Sulfoxonium Ylides with Aryl Thianthrenium Salts via C−S and C−H Bond Activation. Chemistry – An Asian Journal 2025, 20 (10) https://doi.org/10.1002/asia.202401873
91. Gaurav Jaiswal, Subhas Chandra Pan. Ferric Chloride Mediated Dearomative Spirocyclization of Biaryl Ynones: Synthesis of 3,3‐Spiroindanones. Chemistry – An Asian Journal 2025, 20 (10) https://doi.org/10.1002/asia.202401694
92. Takeo Sakai, Takumi Kitamura, Shunya Yokoe, Mayu Uemura, Yuji Mori. Nucleophilic Addition to N-Vinylpyridiniums by Using Ion-Pair Extraction with Tetracyanocyclopentadienides. Synthesis 2025, 57 (09) , 1613-1626. https://doi.org/10.1055/s-0043-1775450
93. Daniel Chong, Paula A. Brooksby, Antony J. Fairbanks. One‐Step Aqueous Synthesis of Glycosyl Pyridinium Salts, Electrochemical Study, and Assessment of Utility as Precursors of Glycosyl Radicals Using Photoredox Catalysis. ChemistryOpen 2025, 13 https://doi.org/10.1002/open.202500183
94. Lirong Han, Hui Zhou, Jinsong Hou, Xiaohao Shi, Qinghan Li. The formation reaction of a carbon–carbon bond promoted by Eosin-Y under visible light. Organic & Biomolecular Chemistry 2025, 23 (16) , 3741-3799. https://doi.org/10.1039/D5OB00141B
95. Shan Wang, Ya-Jian Hu, Xuan Deng, Guang-Yi Zhang, Zichen Xu, Yu-Tao He. Visible light-mediated syntheses of β-pyridyl azides via three-component radical relay. Chinese Chemical Letters 2025, 64 , 111276. https://doi.org/10.1016/j.cclet.2025.111276
96. Xiaotang Chen, Bao-Chen Qian. Benzothiazolines Acting as Carbanion and Radical Transfer Reagents in Carbon–Carbon Bond Construction. Molecules 2025, 30 (8) , 1711. https://doi.org/10.3390/molecules30081711
97. Anjali Aghi, Sankar Sau, Amit Kumar. Exploiting π and hydrogen bonding interactions of a strain-free pyridinium tetrafluoroborate salt for stereoselective synthesis of O -aryl glycosides. Organic Chemistry Frontiers 2025, 12 (7) , 2362-2374. https://doi.org/10.1039/D4QO02401J
98. Bei-Lei Wang, Lin-Yuan Zeng, Pei-Zhen Qu, De-Zhi Yang. Visible light induced deaminative alkylation of pentafluorostyrene promoted by EDA complex. Synthetic Communications 2025, 55 (6) , 476-484. https://doi.org/10.1080/00397911.2025.2462668
99. Xiaotao Qin, Chenglei Yang, Yinjiang Xue, Jinkai Hu, Jinhui Yang, Dianjun Li. Catalyst‐Free Visible Light‐Induced N−N Bond Cleavage for the Synthesis of Iminophosphorane Using Triarylphosphine and N‐Sulfonyl and N‐Acylaminopyridinium Salt. European Journal of Organic Chemistry 2025, 28 (11) https://doi.org/10.1002/ejoc.202401361
100. Samjhana Maharjan, Ravi Kishore Dakoju, Bella Albano, Pamela A. Ondiek, Joseph M. O'Shea, Angel G. Cosme‐Hernandez, Donald Wink, Barry C. Pemberton, Steven A. Lopez, A. Jean‐Luc Ayitou. Recyclable All‐in‐One Organo‐Photo‐Auxiliaries Enabling ( sp 3 )C−( sp 3 )C Coupling Reactions with Diverse Functionalities. Advanced Synthesis & Catalysis 2025, 367 (5) https://doi.org/10.1002/adsc.202400899