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

doi:10.12461/PKU.DXHX202408101

Abstract

Abstract: In recent years, asymmetric free radical reactions catalyzed by organocatalysts have garnered significant attention in the field of organic synthesis. This strategy exhibits mild reaction conditions, and demonstrates excellent regioselectivity and stereoselectivity. Notably, the rapid development of visible light catalysihas provided a new avenue for enhancing these reactions. This review highlights recent progress in asymmetric free radical reactions that combine photocatalysis with organocatalysis: (1) visible light–chiral amine cooperative catalysis, (2) visible light–carbene cooperative catalysis, and (3) visible light–hydrogen bonding catalysis.

Key words: Organic small molecule catalysis, Photocatalysis, Free radical reaction, Asymmetric catalysis

Dan Liu. Recent Advances in Asymmetric Free Radical Reactions via Visible Light-Organocatalytic Synergy[J].University Chemistry, 2025, 40(6): 118-128.

References

[1] 史雷. 大学化学, 2024, 39 (11), 131.
[2] Studer, A.; Curran, D. P. Angew. Chem. Int. Ed. 2016, 55, 58.
[3] Prier, C. K.; Rankic, D. A.; MacMillan, D. W. C. Chem. Rev. 2013, 113, 5322.
[4] MacMillan, D. W. Nature 2008, 455, 304.
[5] Bertelsen, S.; Jørgensen, K. A. Chem. Soc. Rev. 2009, 38, 2178.
[6] Beeson, T. D.; Mastracchio, A.; Hong, J.-B.; Ashton, K.; MacMillan, D. W. C. Science 2007, 316, 582.
[7] Zhu, L.; Wang, D.; Jia, Z.; Lin, Q.; Huang, M.; Luo, S. ACS Catal. 2018, 8, 5466.
[8] Nicewicz, D. A.; MacMillan, D. W. Science 2008, 322, 77.
[9] Nagib, D. A.; Scott, M. E.; MacMillan, D. W. J. Am. Chem. Soc. 2009, 131, 10875.
[10] Shih, H.-W.; Vander Wal, M. N.; Grange, R. L.; MacMillan, D. W. J. Am. Chem. Soc. 2010, 132, 13600.
[11] Li, M.; Sang, Y.; Xue, X.-S.; Cheng, J.-P. J. Org. Chem. 2018, 83, 3333.
[12] Neumann, M.; Füldner, S.; König, B.; Zeitler, K. Angew. Chem. Int. Ed. 2011, 50, 951.
[13] Rigotti, T.; Casado-Sánchez, A.; Cabrera, S.; Pérez-Ruiz, R.; Liras, M.; de la Peña O’Shea, V. A.; Alemán, J. ACS Catal. 2018, 8, 5928.
[14] Arceo, E.; Jurberg, I. D.; Alvarez-Fernandez, A.; Melchiorre, P. Nat. Chem. 2013, 5, 750.
[15] Saux, E. L.; Ma, D.; Bonilla, P.; Holden, C. M.; Lustosa, D.; Melchiorre, P. Angew. Chem. Int. Ed. 2021, 60, 5357.
[16] Silvi, M.; Verrier, C.; Rey, Y. P.; Buzzetti, L.; Melchiorre, P. Nat. Chem. 2017, 9, 868.
[17] Spinnato, D.; Schweitzer-Chaput, B.; Giulio Goti, M. O.; Melchiorre, P. Angew. Chem. Int. Ed. 2020, 59, 9485.
[18] Li, L.-J.; Zhang, J.-C.; Li, W.-P.; Zhang, D.; Duanmu, K.; Yu, H.; Ping, Q.; Yang, Z.-P. J. Am. Chem. Soc. 2024, 146, 9404.
[19] Guin, J.; De Sarkar, S.; Grimme, S.; Studer, A. Angew. Chem. Int. Ed. 2008, 47, 8727.
[20] Bay, A. V.; Scheidt, K. A. Trends in Chem. 2022, 4, 277.
[21] DiRocco, D. A.; Rovis, T. J. Am. Chem. Soc. 2012, 134, 8094.
[22] Choi, H.; Mathi, G. R.; Hong, S.; Hong, S. Nat. Commun. 2022, 13, 1776.
[23] Dondoni, A.; Massi, A. Angew. Chem. Int. Ed. 2008, 47, 4638.
[24] Rono, L. J.; Yayla, H. G.; Wang, D. Y.; Armstrong, M. F.; Knowles, R. R. J. Am. Chem. Soc. 2013, 135, 17735.
[25] Yin, Y.; Dai, Y.; Jia, H.; Li, J.; Bu, L.; Qiao, B.; Zhao, X.; Jiang, Z. J. Am. Chem. Soc. 2018, 140, 6083.
[26] Lahdenperä, A. S. K.; Bacoş, P. D.; Phipps, R. J. J. Am. Chem. Soc. 2022, 144, 22451.
[27] Li, J.; Kong, M.; Qiao, B.; Lee, R.; Zhao, X.; Jiang, Z. Nat. Commun. 2018, 9, 2445.
[28] Proctor, R. S. J.; Davis, H. J.; Phipps, R. J. Science 2018, 360, 419.
[29] Liang, D.; Chen, J.-R.; Tan, L.-P.; He, Z.-W.; Xiao, W.-J. J. Am. Chem. Soc. 2022, 144, 6040.
[30] Che, C.; Lu, Y.-N.; Wang, C.-J. J. Am. Chem. Soc. 2023, 145, 2779.
[31] Fu, Q.; Cao, S.; Wang, J.; Lv, X.; Wang, H.; Zhao, X.; Jiang, Z. J. Am. Chem. Soc. 2024, 146, 8372.
[32] He, F.-S.; Zhang, C.; Jiang, M.; Lou, L.; Wu, J.; Ye, S. Chem. Sci. 2022, 13, 8834.
[33] Zhang, C.; Tang, Z.; Qiu, Y.; Tang, J.; Ye, S.; Li, Z.; Wu, J. Chem. Catal. 2022, 2, 164.
[34] Zhang, J.-L.; He, W.-B.; Hu, X.-Q.; Xu, P.-F. Sci. China Chem. 2024, 67, 945.

Recent Advances in Asymmetric Free Radical Reactions via Visible Light-Organocatalytic Synergy

PDF

Like

Knowledge

Abstract

Cite this article

share this article

References

Related Articles 15

Metrics

Recommended 0

[1]	Jiajia Wang, Sibo Huang, Xijing Gao, Chaoxun Liu, Haibo Zhang. Comprehensive Experimental Design for Ammonia Production via Photocatalytic Nitrate Reduction [J]. University Chemistry, 2025, 40(8): 241-248.
[2]	Yichang Liu, Li An, Dan Qu, Zaicheng Sun. A Comprehensive Design Experiment in the Context of Carbon Peaking and Carbon Neutrality: Determination of Photodegradation Rate Constant of Methylene Blue Catalyzed by PbCrO₄ [J]. University Chemistry, 2025, 40(6): 222-229.
[3]	Meihong Luo, Hongyu Wang. Teaching Reform of Benzoin Oxidation Experiment in the Context of Green Pharmaceutical Chemistry [J]. University Chemistry, 2025, 40(5): 376-382.
[4]	Yulian Hu, Xin Zhou, Xiaojun Han. A Virtual Simulation Experiment on the Design and Property Analysis of CO₂ Reduction Photocatalyst [J]. University Chemistry, 2025, 40(3): 30-35.
[5]	Dongdong Guo, Yongpo Zhang, Congcong Yin, Jinzhong Zhao, Yongqiang Wang. Photocatalytic Oxidation for the Green Synthesis of β-Naphthaldehyde [J]. University Chemistry, 2025, 40(2): 378-384.
[6]	Qin Li, Ziyao Jia, Ye Chen, Mingze Ma, Lin Li, Tao Huang. A Journey into the Enigmatic World of Pickering Emulsion: A Chemical Science Popularization Experiment [J]. University Chemistry, 2024, 39(9): 311-318.
[7]	Hong Lu, Yidie Zhai, Xingxing Cheng, Yujia Gao, Qing Wei, Hao Wei. Advancements and Expansions in the Proline-Catalyzed Asymmetric Aldol Reaction [J]. University Chemistry, 2024, 39(5): 154-162.
[8]	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 [J]. University Chemistry, 2024, 39(5): 201-208.
[9]	Zijian Jiang, Yuang Liu, Yijian Zong, Yong Fan, Wanchun Zhu, Yupeng Guo. Preparation of Nano Zinc Oxide by Microemulsion Method and Study on Its Photocatalytic Activity [J]. University Chemistry, 2024, 39(5): 266-273.
[10]	Yurong Tang, Yunren Shi, Yi Xu, Bo Qin, Yanqin Xu, Yunfei Cai. Innovative Experiment and Course Transformation Practice of Visible-Light-Mediated Photocatalytic Synthesis of Isoquinolinone [J]. University Chemistry, 2024, 39(5): 296-306.
[11]	Xin Zhou, Zhi Zhang, Yun Yang, Shuijin Yang. A Study on the Enhancement of Photocatalytic Performance in C/Bi/Bi₂MoO₆ Composites by Ferroelectric Polarization: A Recommended Comprehensive Chemical Experiment [J]. University Chemistry, 2024, 39(4): 296-304.
[12]	Tingyu Zhu, Hui Zhang, Wenwei Zhang. Exploration and Practice of Ideological and Political Education in the Course of Experiments on Chemical Functional Molecules: Synthesis and Catalytic Performance Study of Chiral Mn(III)Cl-Salen Complex [J]. University Chemistry, 2024, 39(4): 75-80.
[13]	Jingyu Cai, Xiaoyu Miao, Yulai Zhao, Longqiang Xiao. Exploratory Teaching Experiment Design of FeOOH-RGO Aerogel for Photocatalytic Benzene to Phenol [J]. University Chemistry, 2024, 39(4): 169-177.
[14]	Bin Zhang, Tiantian Li, Yitian Song, Ying Cheng, Jiarong Chen. Photoredox and Copper Co-Catalyzed Synthesis of α-Methyl-4-Biphenylacetonitrile [J]. University Chemistry, 2024, 39(12): 235-243.
[15]	Zhenyu Guo, Yuhang Li, Shuai Chen, Chengjian Zhu, Jin Xie. Photoredox/Nickel-Catalyzed Synthesis of 4′-Methoxypropiophenone [J]. University Chemistry, 2024, 39(1): 210-217.