Recent Advance in the Transition-Metal Free Coupling Reactions for the Construction of C-X Bonds Induced by Light
- Corresponding author: Yao Qiuli, yao.qiuli@zmc.edu.cn
Citation:
Ren Linjing, Ran Maogang, He Jiaxin, Qian Yan, Yao Qiuli. Recent Advance in the Transition-Metal Free Coupling Reactions for the Construction of C-X Bonds Induced by Light[J]. Chinese Journal of Organic Chemistry,
;2019, 39(6): 1583-1595.
doi:
10.6023/cjoc201812042
Chatt, J.; Shaw, B. L. J. Chem. Soc. 1960, 1718.
Suzuki, K. Pure Appl. Chem. 1994, 66, 2175.
doi: 10.1351/pac199466102175
Davies, J.; Svejstrup, T. D.; Reina, D. F.; Sheikh, N. S.; Leonori, D. J. Am. Chem. Soc. 2016, 138, 8092.
doi: 10.1021/jacs.6b04920
Margrey, K. A.; Levens, A.; Nicewicz, D. A. Angew. Chem., Int. Ed. 2017, 56, 15644.
doi: 10.1002/anie.201709523
Sakakibara, Y.; Ito, E.; Kawakami, T.; Yamada, S.; Murakami, K.; Itami, K. Chem. Lett. 2017, 46, 1014.
doi: 10.1246/cl.170321
Romero, N. A.; Margrey, K. A.; Tay, N. E.; Nicewicz, D. A. Science 2015, 349, 1326.
doi: 10.1126/science.aac9895
Tay, N. E. S.; Nicewicz, D. A. J. Am. Chem. Soc. 2017, 139, 16100.
doi: 10.1021/jacs.7b10076
Meyer, A. U.; Berger, A. L.; König, B. Chem. Commun. 2016, 52, 10918.
doi: 10.1039/C6CC06111G
Das, S.; Natarajan, P.; König, B. Chem.-Eur. J. 2017, 23, 18161
doi: 10.1002/chem.201705442
Zhang, L.; Yi, H.; Wang, J.; Lei, A. J. Org. Chem. 2017, 82, 10704.
doi: 10.1021/acs.joc.7b01841
Samanta, S.; Ravi, C.; Rao, S. N.; Joshi, A.; Adimurthy, S. Org. Biomol. Chem. 2017, 15, 9590.
doi: 10.1039/C7OB02504A
(a) Swenson, R. E.; Sowin, T. J.; Zhang, H. Q. J. Org. Chem. 2002, 67, 9182.
(b) Yang, H.; Carter, R. G.; Zakharov, L. N. J. Am. Chem. Soc. 2008, 130, 9238.
Curti, C.; Laget, M.; Carle, A. O.; Gellis, A.; Vanelle, P. Eur. J. Med. Chem. 2007, 42, 880.
doi: 10.1016/j.ejmech.2006.12.015
Xia, D.; Miao, T.; Li, P.; Wang, L. Chem.-Asian J. 2015, 10, 1919.
doi: 10.1002/asia.v10.9
Yang, W.; Yang, S.; Li, P.; Wang, L. Chem. Commun. 2015, 51, 7520.
doi: 10.1039/C5CC00878F
Yang, D.; Huang, B.; Wei, W.; Li, J.; Lin, G.; Liu, Y.; Ding, J.; Suna, P.; Wang, H. Green Chem. 2016, 18, 5630.
doi: 10.1039/C6GC01403H
Wang, H.; Lu, Q.; Chiang, C. W.; Luo, Y.; Zhou, J.; Wang, G.; Lei, A. Angew. Chem., Int. Ed. 2017, 56, 595.
doi: 10.1002/anie.201610000
Meyer, A. U.; Jäger, S.; Hari, D. P.; König, B. Adv. Synth. Catal. 2015, 357, 2050.
doi: 10.1002/adsc.v357.9
Meyer, A. U.; Straková, K.; Slanina, T.; König, B. Chem.-Eur. J. 2016, 22, 8694.
doi: 10.1002/chem.v22.25
Sun, D.; Zhang, R. Org. Chem. Front. 2017, 5, 92.
doi: 10.3389/fchem.2017.00092
Cai, S.; Xu, Y.; Chen, D.; Li, L.; Chen, Q.; Huang, M.; Weng, W. Org. Lett. 2016, 18, 2990.
doi: 10.1021/acs.orglett.6b01353
Sun, P.; Yang, D.; Wei, W.; Jiang, M.; Wang, Z.; Zhang, L.; Zhang, H.; Zhang, Z.; Wang, Y.; Wang, H. Green Chem. 2017, 19, 4785.
doi: 10.1039/C7GC01891F
Mitra, S.; Ghosh, M.; Mishra, S.; Hajra, A. J. Org. Chem. 2015, 80, 8275.
doi: 10.1021/acs.joc.5b01369
Yadav, A. K.; Yadav, L. D. S. Tetrahedron Lett. 2015, 56, 6696.
doi: 10.1016/j.tetlet.2015.10.048
Luo, K.; Chen, Y. Z.; Yang, W. C.; Zhu, J.; Wu, L. Org. Lett. 2016, 18, 452.
doi: 10.1021/acs.orglett.5b03497
Li, Q.; Zhao, X.; Li, Y.; Huang, M.; Kim, J. K.; Wu, Y. Org. Biomol. Chem. 2017, 15, 9775.
doi: 10.1039/C7OB02478A
Shi, Y.; Chen, R.; Guo, K.; Meng, F.; Cao, S.; Gu, C.; Zhu, Y. Tetrahedron Lett. 2018, 59, 2062.
doi: 10.1016/j.tetlet.2018.04.040
Qian, H. F.; Li, C. K.; Zhou, Z. H.; Tao, Z. K.; Shoberu, A.; Zou, J. P. Org. Lett. 2018, 20, 5947.
doi: 10.1021/acs.orglett.8b02639
Grandjean, J. M.; Nicewicz, D. A. Angew. Chem., Int. Ed. 2013, 52, 3967.
doi: 10.1002/anie.v52.14
Morse, P. D.; Nicewicz, D. A. Chem. Sci. 2015, 6, 270.
doi: 10.1039/C4SC02331E
Gesmundo, N. J.; Grandjean, J. M.; Nicewicz, D. A. Org. Lett. 2015, 17, 1316.
doi: 10.1021/acs.orglett.5b00316
Roslan, I. I.; Ng, K. H.; Gondal, M. A.; Basheer, C.; Dastageer, M. A.; Jaenicke, S.; Chuah, G. K. Adv. Synth. Catal. 2018, 360, 1584.
doi: 10.1002/adsc.v360.8
Zhou, H.; Yang, X.; Li, S.; Zhu, Y.; Li, Y.; Zhang, Y. Org. Biomol. Chem. 2018, 16, 6728.
doi: 10.1039/C8OB01844H
Xiao, T.; Li, L.; Lin, G.; Wang, Q.; Zhang, P.; Mao, Z.-W.; Zhou, L. Green Chem. 2014, 16, 2418.
doi: 10.1039/C3GC42517G
Gu, L.; Jin, C.; Liu, J.; Ding, H.; Fan, B. Chem. Commun. 2014, 50, 4643.
doi: 10.1039/C4CC01487A
Fang, J.; Shen, W.-G.; Ao, G.-Z.; Liu, F. Org. Chem. Front. 2017, 4, 2049.
doi: 10.1039/C7QO00473G
Li, J.; Caiuby, C. A. D.; Paixão, M. W.; Li, C. Eur. J. Org. Chem. 2018, 2018, 2498.
doi: 10.1002/ejoc.201701487
Borpatra, P. J.; Deb, M. L.; Baruah, P. K. Tetrahedron Lett. 2017, 58, 4006.
doi: 10.1016/j.tetlet.2017.09.018
Yang, J. C.; Zhang, J. Y.; Zhang, J. J.; Duan, X. H.; Guo, L. N. J. Org. Chem. 2018, 83, 1598.
doi: 10.1021/acs.joc.7b02861
Huang, M. H.; Zhu, Y. L.; Hao, W. J.; Wang, A. F.; Wang, D. C.; Liu, F. Adv. Synth. Catal. 2017, 359, 2229.
doi: 10.1002/adsc.v359.13
Xie, X.; Li, P.; Shi, Q.; Wang, L. Org. Biomol. Chem. 2017, 15, 7678.
doi: 10.1039/C7OB01747B
Shi, Q.; Li., P.; Zhang, Y.; Wang, L. Org. Chem. Front. 2017, 4, 1322.
doi: 10.1039/C7QO00152E
Gu, L.; Jin, C.; Wang, W.; He, Y.; Yang, G.; Li, G. Chem. Commun. 2017, 53, 4203.
doi: 10.1039/C6CC10305G
Jin, C.; Su, L.; Ma, D.; Cheng, M. New J. Chem. 2017, 41, 14053.
doi: 10.1039/C7NJ03144K
Yu, Y.; Yuan, W.; Huang, H.; Cai, Z.; Liu, P.; Sun, P. J. Org. Chem. 2018, 83, 1654.
doi: 10.1021/acs.joc.7b03080
He, Y.; Yan, B.; Tao, H.; Zhang, Y.; Li, Y. Org. Biomol. Chem. 2018, 16, 3816.
doi: 10.1039/C8OB00240A
Zijian Zhao , Yanxin Shi , Shicheng Li , Wenhong Ruan , Fang Zhu , Jijun Jiang . A New Exploration of the Preparation of Polyacrylic Acid by Free Radical Polymerization Based on the Concept of Green Chemistry. University Chemistry, 2024, 39(5): 315-324. doi: 10.3866/PKU.DXHX202311094
Fei Liu , Dong-Yang Zhao , Kai Sun , Ting-Ting Yu , Xin Wang . Comprehensive Experimental Design for Photochemical Synthesis, Analysis, and Characterization of Seleno-Containing Medium-Sized N-Heterocycles. University Chemistry, 2024, 39(3): 369-375. doi: 10.3866/PKU.DXHX202309047
Zhen Yao , Bing Lin , Youping Tian , Tao Li , Wenhui Zhang , Xiongwei Liu , Wude Yang . Visible-Light-Mediated One-Pot Synthesis of Secondary Amines and Mechanistic Exploration. University Chemistry, 2024, 39(5): 201-208. doi: 10.3866/PKU.DXHX202311033
Yinuo Wang , Siran Wang , Yilong Zhao , Dazhen Xu . Selective Synthesis of Diarylmethyl Anilines and Triarylmethanes via Multicomponent Reactions: Introduce a Comprehensive Experiment of Organic Chemistry. University Chemistry, 2024, 39(8): 324-330. doi: 10.3866/PKU.DXHX202401063
Jihua Deng , Xinshi Wu , Dichang Zhong . Exploration of Green Teaching and Ideological and Political Education in Chemical Experiment of “Preparation of Ammonium Ferrous Sulfate”. University Chemistry, 2024, 39(10): 325-329. doi: 10.12461/PKU.DXHX202405046
Tingting Yu , Si Chen , Lianglong Sun , Tongtong Shi , Kai Sun , Xin Wang . Comprehensive Experimental Design for the Photochemical Synthesis, Analysis, and Characterization of Difluoropyrroles. University Chemistry, 2024, 39(11): 196-203. doi: 10.3866/PKU.DXHX202401022
Tongyan Yu , Pan Xu . Visible-Light Photocatalyzed Radical Rearrangement Reaction. University Chemistry, 2025, 40(7): 169-176. doi: 10.12461/PKU.DXHX202409070
Dan Liu . 可见光-有机小分子协同催化的不对称自由基反应研究进展. University Chemistry, 2025, 40(6): 118-128. doi: 10.12461/PKU.DXHX202408101
Zihan Lin , Wanzhen Lin , Fa-Jie Chen . Electrochemical Modifications of Native Peptides. University Chemistry, 2025, 40(3): 318-327. doi: 10.12461/PKU.DXHX202406089
Yifan Liu , Haonan Peng . AI-Assisted New Era in Chemistry: A Review of the Application and Development of Artificial Intelligence in Chemistry. University Chemistry, 2025, 40(7): 189-199. doi: 10.12461/PKU.DXHX202405182
Yongjian Zhang , Fangling Gao , Hong Yan , Keyin Ye . Electrochemical Transformation of Organosulfur Compounds. University Chemistry, 2025, 40(5): 311-317. doi: 10.12461/PKU.DXHX202407035
Xue Dong , Xiaofu Sun , Shuaiqiang Jia , Shitao Han , Dawei Zhou , Ting Yao , Min Wang , Minghui Fang , Haihong Wu , Buxing Han . 碳修饰的铜催化剂实现安培级电流电化学还原CO2制C2+产物. Acta Physico-Chimica Sinica, 2025, 41(3): 2404012-. doi: 10.3866/PKU.WHXB202404012
Feng Han , Fuxian Wan , Ying Li , Congcong Zhang , Yuanhong Zhang , Chengxia Miao . Comprehensive Organic Chemistry Experiment: Phosphotungstic Acid-Catalyzed Direct Conversion of Triphenylmethanol for the Synthesis of Oxime Ethers. University Chemistry, 2025, 40(3): 342-348. doi: 10.12461/PKU.DXHX202405181
Yihao Zhao , Jitian Rao , Jie Han . Synthesis and Photochromic Properties of 3,3-Diphenyl-3H-Naphthopyran: Design and Teaching Practice of a Comprehensive Organic Experiment. University Chemistry, 2024, 39(10): 149-155. doi: 10.3866/PKU.DXHX202402050
Yinwu Su , Xuanwen Zheng , Jianghui Du , Boda Li , Tao Wang , Zhiyan Huang . Green Synthesis of 1,3-Dibromoacetone Using Halogen Exchange Method: Recommending a Basic Organic Synthesis Teaching Experiment. University Chemistry, 2024, 39(5): 307-314. doi: 10.3866/PKU.DXHX202311092
Wanmin Cheng , Juan Du , Peiwen Liu , Yiyun Jiang , Hong Jiang . Photoinitiated Grignard Reagent Synthesis and Experimental Improvement in Triphenylmethanol Preparation. University Chemistry, 2024, 39(5): 238-242. doi: 10.3866/PKU.DXHX202311066
Yunchao Li , Shanying Chen , Ke Qi , Kangning Huo , Shuxin Li , Jingyi Li , Ying Wei , Louzhen Fan . A New Colloid Electrophoresis Experiment Incorporating Characteristics of Inquiry Learning and Ideological and Political Education. University Chemistry, 2024, 39(2): 47-51. doi: 10.3866/PKU.DXHX202308063
Wenjiang LI , Pingli GUAN , Rui YU , Yuansheng CHENG , Xianwen WEI . C60-MoP-C nanoflowers van der Waals heterojunctions and its electrocatalytic hydrogen evolution performance. Chinese Journal of Inorganic Chemistry, 2024, 40(4): 771-781. doi: 10.11862/CJIC.20230289
Zhilian Liu , Wengui Wang , Hongxiao Yang , Yu Cui , Shoufeng Wang . Ideological and Political Education Design for the Synthesis of Irinotecan Drug Intermediate 7-Ethyl Camptothecin. University Chemistry, 2024, 39(2): 89-93. doi: 10.3866/PKU.DXHX202306012
Ling Liu , Haibin Wang , Genrong Qiang . Curriculum Ideological and Political Design for the Comprehensive Preparation Experiment of Ethyl Benzoate Synthesized from Benzyl Alcohol. University Chemistry, 2024, 39(2): 94-98. doi: 10.3866/PKU.DXHX202304080