Citation:
Yansong Xiao, Yi Huang, Xingxing Ma, Qiuling Song. The Matteson Reaction in Organic Synthesis: From Fundamentals to Frontiers[J]. University Chemistry,
;2025, 40(10): 114-120.
doi:
10.12461/PKU.DXHX202411023
-
The Matteson reaction has garnered significant attention in recent years as one of the cornerstone methodologies for organoboron compound synthesis, demonstrating remarkable utility in complex molecule construction and pharmaceutical development. This comprehensive review systematically examines the Matteson reaction, beginning with an elucidation of its fundamental principles and mechanistic underpinnings to establish a conceptual framework. Subsequently, we provide a critical analysis of contemporary advancements in its practical applications, particularly highlighting its pivotal role as a key transformation in the total synthesis of complex natural products and the production of pharmaceutically relevant intermediates.
-
-
-
[1]
Essman, J. Z.; Sharma, H. A.; Jacobsen, E. N. Synlett 2023, 34 (18), 2061.
-
[2]
-
[3]
Sträter, N. Angew. Chem. Int. Ed. 2011, 50 (34), 7730.
-
[4]
Brown, H. C.; Snyder, C.; Rao, B. C. S.; Zweifel, G. Tetrahedron 1986, 42 (20), 5505.
-
[5]
Miyaura, N.; Tanabe, Y.; Suginome, H.; Suzuki, A. J. Organomet. Chem. 1982, 233 (2), C13.
-
[6]
-
[7]
-
[8]
Matteson, D. S.; Mah, R.W. H. J. Am. Chem. Soc. 1963, 85 (17), 2599.
-
[9]
Matteson, D. S.; Majumdar, D. J. Am. Chem. Soc. 1980, 102 (25), 7588.
-
[10]
Matteson, D. S.; Ray, R. J. Am. Chem. Soc. 1980, 102 (25), 7590.
-
[11]
Lazzeretti, P. J. Phys.: Condens. Matter 2017, 29 (44), 443001.
-
[12]
Sharma, H. A.; Essman, J. Z.; Jacobsen, E. N. Science 2021, 374, 752.
-
[13]
Kinsinger, T.; Kazmaier, U. Org. Lett. 2022, 24 (20), 3599.
-
[14]
Reisman, S. E.; Maimone, T. J. Acc. Chem. Res. 2021, 54 (8), 1815.
-
[15]
Dutheuil, G.; Webster, M. P.; Worthington, P. A.; Aggarwal, V. K. Angew. Chem. Int. Ed. 2009, 48 (34), 6317.
-
[16]
Balieu, S.; Hallett, G. E.; Burns, M.; Bootwicha, T.; Studley, J.; Aggarwal, V. K. J. Am. Chem. Soc. 2015, 137 (13), 4398.
-
[17]
Xie, Q.; Dong, G. J. Am. Chem. Soc. 2021, 143 (36), 14422.
-
[18]
Xie, Q.; Dong, G. J. Am. Chem. Soc. 2022, 144 (19), 8498.
-
[19]
Zou, H.-N.; Huang, M.-L.; Huang, M.-Y.; Su, Y.-X.; Zhang, J.-W.; Zhang, X.-Y.; Zhu, S.-F. Chem. Sci. 2023, 14 (34), 9186.
-
[20]
Fang, T.; Wang, L.; Wu, M.; Qi, X.; Liu, C. Angew. Chem. Int. Ed. 2024, 63 (3), e202315227.
-
[21]
-
[22]
Qi, W.; Zhen, J.; Xu, X.; Du, X.; Li, Y.; Yuan, H.; Guan, Y.; Wei, X.; Wang, Z.; Liang, G.; et al. Org. Lett. 2021, 23 (15), 5988.
-
[1]
-
-
-
[1]
Yan Kong , Wei Wei , Lekai Xu , Chen Chen . Electrochemical Synthesis of Organonitrogen Compounds from N-integrated CO2 Reduction Reaction. Acta Physico-Chimica Sinica, 2024, 40(8): 2307049-0. doi: 10.3866/PKU.WHXB202307049
-
[2]
Lili Jiang , Shaoyu Zheng , Xuejiao Liu , Xiaomin Xie . Copper-Catalyzed Oxidative Coupling Reactions for the Synthesis of Aryl Sulfones: A Fundamental and Exploratory Experiment for Undergraduate Teaching. University Chemistry, 2025, 40(7): 267-276. doi: 10.12461/PKU.DXHX202408004
-
[3]
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
-
[4]
Jiaming Xu , Yu Xiang , Weisheng Lin , Zhiwei Miao . Research Progress in the Synthesis of Cyclic Organic Compounds Using Bimetallic Relay Catalytic Strategies. University Chemistry, 2024, 39(3): 239-257. doi: 10.3866/PKU.DXHX202309093
-
[5]
Aidang Lu , Yunting Liu , Yanjun Jiang . Comprehensive Organic Chemistry Experiment: Synthesis and Characterization of Triazolopyrimidine Compounds. University Chemistry, 2024, 39(8): 241-246. doi: 10.3866/PKU.DXHX202401029
-
[6]
Qianlang Wang , Jijun Sun , Qian Chen , Quanqin Zhao , Baojuan Xi . The Appeal of Organophosphorus Compounds: Clearing Their Name. University Chemistry, 2025, 40(4): 299-306. doi: 10.12461/PKU.DXHX202405205
-
[7]
Guoqiang Chen , Zixuan Zheng , Wei Zhong , Guohong Wang , Xinhe Wu . Molten Intermediate Transportation-Oriented Synthesis of Amino-Rich g-C3N4 Nanosheets for Efficient Photocatalytic H2O2 Production. Acta Physico-Chimica Sinica, 2024, 40(11): 2406021-0. doi: 10.3866/PKU.WHXB202406021
-
[8]
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
-
[9]
Yerong Chen , Bingbin Yang , Xinglei He , Yuqi Lin , Keyin Ye . Enzyme-Directed Evolution Enables Bioconversion of Organosilicon Compounds. University Chemistry, 2025, 40(10): 121-129. doi: 10.12461/PKU.DXHX202411054
-
[10]
Jiajie Li , Xiaocong Ma , Jufang Zheng , Qiang Wan , Xiaoshun Zhou , Yahao Wang . Recent Advances in In-Situ Raman Spectroscopy for Investigating Electrocatalytic Organic Reaction Mechanisms. University Chemistry, 2025, 40(4): 261-276. doi: 10.12461/PKU.DXHX202406117
-
[11]
Yan Qi , Yueqin Yu , Weisi Guo , Yongjun Liu . 过渡金属参与的有机反应案例教学与实践探索. University Chemistry, 2025, 40(6): 111-117. doi: 10.12461/PKU.DXHX202411021
-
[12]
Zhongyan Cao , Youzhi Xu , Menghua Li , Xiao Xiao , Xianqiang Kong , Deyun Qian . Electrochemically Driven Denitrative Borylation and Fluorosulfonylation of Nitroarenes. University Chemistry, 2025, 40(4): 277-281. doi: 10.12461/PKU.DXHX202407017
-
[13]
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
-
[14]
Qianping Li , Hua Guan , Changfeng Wan , Yonghai Song , Jianwen Jiang . 大学有机化学复习课项目式教学——以“液晶化合物4-正戊基苯甲酸-4′-正戊基苯酯的合成路线设计与产品制备”为例. University Chemistry, 2025, 40(8): 100-116. doi: 10.12461/PKU.DXHX202410070
-
[15]
Xilin Zhao , Xingyu Tu , Zongxuan Li , Rui Dong , Bo Jiang , Zhiwei Miao . Research Progress in Enantioselective Synthesis of Axial Chiral Compounds. University Chemistry, 2024, 39(11): 158-173. doi: 10.12461/PKU.DXHX202403106
-
[16]
Weina Wang , Lixia Feng , Fengyi Liu , Wenliang Wang . Computational Chemistry Experiments in Facilitating the Study of Organic Reaction Mechanism: A Case Study of Electrophilic Addition of HCl to Asymmetric Alkenes. University Chemistry, 2025, 40(3): 206-214. doi: 10.12461/PKU.DXHX202407022
-
[17]
Tianyun Chen , Ruilin Xiao , Xinsheng Gu , Yunyi Shao , Qiujun Lu . Synthesis, Crystal Structure, and Mechanoluminescence Properties of Lanthanide-Based Organometallic Complexes. University Chemistry, 2024, 39(5): 363-370. doi: 10.3866/PKU.DXHX202312017
-
[18]
Xinyi Zhang , Kai Ren , Yanning Liu , Zhenyi Gu , Zhixiong Huang , Shuohang Zheng , Xiaotong Wang , Jinzhi Guo , Igor V. Zatovsky , Junming Cao , Xinglong Wu . Progress on Entropy Production Engineering for Electrochemical Catalysis. Acta Physico-Chimica Sinica, 2024, 40(7): 2307057-0. doi: 10.3866/PKU.WHXB202307057
-
[19]
Wenjie SHI , Fan LU , Mengwei CHEN , Jin WANG , Yingfeng HAN . Synthesis and host-guest properties of imidazolium-functionalized zirconium metal-organic cage. Chinese Journal of Inorganic Chemistry, 2025, 41(1): 105-113. doi: 10.11862/CJIC.20240360
-
[20]
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
-
[1]
Metrics
- PDF Downloads(1)
- Abstract views(67)
- HTML views(9)