不对称C―H/C―H交叉脱氢偶联反应研究进展

doi:10.3866/PKU.DXHX202305034

Abstract

Abstract:

In recent years, the cross-dehydrogenative coupling (CDC) reaction has received widespread attention in the field of organic synthetic chemistry. This strategy avoids the pre-functionalization of substrates in the reactions that form carbon–carbon bonds. It demonstrates high atomic economy and aligns with the development requirements of green chemistry. Furthermore, asymmetric CDC reactions can realize stereoselective construction of carbon–carbon bonds, which currently constitutes a key area of research in organic synthesis. This paper reviews the research progress in asymmetric CDC reactions and provides a perspective on the future development direction in this field.

Key words: Asymmetric catalysis, Green chemistry, C―H activation, C―C bond formation, Research progress

Tianyu Li, Danqing Wu, Jiajun Liu, Dazhen Xu, Zhiwei Miao. Research Progress of Asymmetric C―H/C―H Cross Dehydrogenation Coupling Reaction[J].University Chemistry, 2023, 38(12): 165-180.

Figures/Tables 29

References 44

1	Li C. J. Acc. Chem. Res. 2009, 42, 335. doi: 10.1021/ar800164n
2	Huang Y. T. ; Chen Q. Chin. J. Org. Chem. 2021, 41, 4138. doi: 10.6023/cjoc202107044
3	Prakash T. P. ; Roman M. ; Bimal K. B. Chem. Asian J. 2019, 14, 6. doi: 10.1002/asia.201801237
4	Begur V. V. ; Jayaraman D. ; Kiran R. B. ; Yogesh S. ; Kaliyamoorthy A. ; Kandikere R. P. Tetrahedron Lett. 2017, 58, 803. doi: 10.1016/j.tetlet.2017.01.035
5	Simon A. G. ; Thomas K. ; Li C. J. Angew. Chem. Int. Ed. 2014, 53, 74. doi: 10.1002/anie.201304268
6	Li C. J. Chin. J. Chem. 2022, 40, 838. doi: 10.1002/cjoc.202100796
7	Martin K. ; Devarajulu S. Synthesis 2011, 3, 353.
8	Li C. J. ; Li Z. P. Pure Appl. Chem. 2006, 78, 935. doi: 10.1351/pac200678050935
9	Tian T. ; Li Z. P. ; Li C. J. Green Chem. 2021, 23, 6789. doi: 10.1039/D1GC01871J
10	Caroline J. S. Chem. Asian J. 2010, 5, 436. doi: 10.1002/asia.200900487
11	Sun C. L. ; Li B. J. ; Shi Z. J. Chem. Rev. 2011, 111, 1293. doi: 10.1021/cr100198w
12	Charles S. Y. ; Vy M. D. Chem. Rev. 2011, 111, 1215. doi: 10.1021/cr100280d
13	Naeem G. ; Bertrand S. ; Martin K. Catal. Sci. Technol. 2014, 4, 2778. doi: 10.1039/C4CY00544A
14	Ana M. F. P. ; Armando J. L. P. ChemCatChem 2018, 10, 3354. doi: 10.1002/cctc.201800582
15	Zhang Y. ; Feng B. N. Chin. J. Org. Chem. 2014, 34, 2406. doi: 10.6023/cjoc201408030
16	Cheng M. X. ; Yang S. D. Synlett 2017, 28, 159.
17	Shikha G. Org. Biomol. Chem. 2019, 17, 9683. doi: 10.1039/C9OB02113B
18	James A. A. Chem. Soc. Rev. 2010, 39, 540. doi: 10.1039/B907809F
19	Chrzanowska M. ; Grajewska A. ; Rozwadowska M. D. Chem. Rev. 2016, 116, 12369. doi: 10.1021/acs.chemrev.6b00315
20	Liu W. ; Liu S. ; Jin R. ; Guo H. ; Zhao J. Org. Chem. Front. 2015, 2, 288. doi: 10.1039/C4QO00294F
21	Li Z. P. ; Li C. J. Org. Lett. 2004, 6, 4997. doi: 10.1021/ol047814v
22	Li Z. P. ; Patricia D. M. ; Li C. J. Tetrahedron-Asymmetry 2006, 17, 590. doi: 10.1016/j.tetasy.2006.02.007
23	Yu J. B. ; Li Z. H. ; Jia K. Y. ; Jiang Z. J. ; Liu M. L. ; Su W. K. Tetrahedron Lett. 2013, 54, 2006. doi: 10.1016/j.tetlet.2013.02.007
24	Perepichka I. ; Kundu S. ; Hearne Z. ; Li C. J. Org. Biomol. Chem. 2015, 13, 447. doi: 10.1039/C4OB02138J
25	Sun S. T. ; Li C. K. ; Paul E. F. ; Lou H. X. ; Liu L. Org. Lett. 2015, 17, 1684. doi: 10.1021/acs.orglett.5b00447
26	Xie Z. Y. ; Liu X. G. ; Liu L. Org. Lett. 2016, 18, 2982. doi: 10.1021/acs.orglett.6b01328
27	Huang T. Y. ; Liu X. H. ; Lang J. W. ; Xu J. ; Lin L. L. ; Feng X. M. ACS Catal. 2017, 7, 5654. doi: 10.1021/acscatal.7b01912
28	Gaurav K. ; Shailesh V. ; Amamudin A. ; Rukhsana I. K. Catal. Commun. 2017, 99, 94. doi: 10.1016/j.catcom.2017.05.026
29	Zhang Z. H. ; Dong X. Y. ; Du X. Y. ; Gu Q. S. ; Li Z. L. ; Liu X. Y. Nat. Commun. 2019, 10 (5689), 1.
30	Gao P. S. ; Weng X. J. ; Wang Z. H. ; Zheng C. ; Sun B. ; Chen Z. H. ; You S. L. ; Mei T. S. Angew. Chem. Int. Ed. 2020, 59, 15254. doi: 10.1002/anie.202005099
31	Liu L. ; Guo K. X. ; Tian Y. ; Yang C. J. ; Gu Q. S. ; Li Z. L. ; Ye L. ; Liu X. Y. Angew. Chem. Int. Ed. 2021, 60, 26710. doi: 10.1002/anie.202110233
32	Benfatti F. ; Capdevila M. G. ; Zoli L. ; Benedetto E. ; Cozzi P. G. Chem. Commun. 2009, 5919
33	Guo C. ; Song J. ; Luo S.-W. ; Gong L. Z. Angew. Chem. Int. Ed. 2010, 49, 5558. doi: 10.1002/anie.201002108
34	Zhang G. ; Ma Y. X. ; Wang S. L. ; Kong W. D. ; Wang R. Chem. Sci. 2013, 4, 2645. doi: 10.1039/c3sc50604e
35	Tan Y. Q. ; Yuan W. ; Gong L. ; Eric M. Angew. Chem. Int. Ed. 2015, 54, 13045. doi: 10.1002/anie.201506273
36	Wang G. ; Xin X. D. ; Wang Z. H. ; Lu G. ; Ma Y. D. ; Liu L. Nat. Commun. 2019, 10 (559), 1.
37	Xin X. D. ; Pan X. H. ; Meng Z. L. ; Liu X. G. ; Liu L. Org. Chem. Front. 2019, 6, 1448. doi: 10.1039/C9QO00123A
38	Yang X. R. ; Xie Z. X. ; Li Y. ; Zhang Y. Chem. Sci. 2020, 11, 4741. doi: 10.1039/D0SC00683A
39	Yu J. B. ; Ying P. ; Wang H. ; Xiang K. Y. ; Su W. K. Adv. Synth. Catal. 2020, 362, 893. doi: 10.1002/adsc.201901363
40	Liu X. G. ; Zhao C. Y. ; Zhu R. X. ; Liu L. Angew. Chem. Int. Ed. 2021, 60, 18499. doi: 10.1002/anie.202105594
41	Hiromichi E. ; Kenji M. ; Takuya O. ; Takashi K. ; Tsutomu K. J. Am. Chem. Soc. 2010, 132, 13633. doi: 10.1021/ja105442m
42	Tian J. M. ; Wang A. F. ; Yang J. S. ; Zhao X. J. ; Tu Y. Q. ; Zhang S. Y. ; Chen Z. M. Angew. Chem. Int. Ed. 2019, 58, 11023. doi: 10.1002/anie.201903435
43	Pan X. G. ; Wang Z. H. ; Kan L. L. ; Mao Y. ; Zhu Y. S. ; Liu L. Chem. Sci. 2020, 11, 2414. doi: 10.1039/C9SC05894J
44	Wang Z. H. ; Zhu Y. S. ; Pan X. G. ; Wang G. ; Liu L. Angew. Chem. Int. Ed. 2020, 59, 3053. doi: 10.1002/anie.201912739

[1]	Yifan Liu, Haonan Peng. AI-Assisted New Era in Chemistry: A Review of the Application and Development of Artificial Intelligence in Chemistry [J]. University Chemistry, 2025, 40(7): 189-199.
[2]	Dan Liu. Recent Advances in Asymmetric Free Radical Reactions via Visible Light-Organocatalytic Synergy [J]. University Chemistry, 2025, 40(6): 118-128.
[3]	Yongjian Zhang, Fangling Gao, Hong Yan, Keyin Ye. Electrochemical Transformation of Organosulfur Compounds [J]. University Chemistry, 2025, 40(5): 311-317.
[4]	Zihan Lin, Wanzhen Lin, Fa-Jie Chen. Electrochemical Modifications of Native Peptides [J]. University Chemistry, 2025, 40(3): 318-327.
[5]	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 [J]. University Chemistry, 2025, 40(3): 342-348.
[6]	Yuxiao Hu, Bingbing Huang, Wenju Chang, Jie Shen. Oxygen-Centered Radicals [J]. University Chemistry, 2025, 40(2): 216-227.
[7]	Mengxia Feng, Xiaohong Li, Jianqiang Hu, Liangbin Huang. Design of an Undergraduate Experiment on the Synthesis of Cyclopent-2-enone Derivatives Catalyzed by Rare Earth Metals [J]. University Chemistry, 2025, 40(2): 341-347.
[8]	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.
[9]	Ke Liu, Mingjing Deng, Jingbo Chang, Ailing Wang, Guoshuai Wu, Longyang Dian. Electrochemistry Mediated Direct Amination to Construct the Hemiaminal Ether Skeletons (HESs) [J]. University Chemistry, 2025, 40(2): 272-277.
[10]	Shuhui Li, Yujing Zhou, Haitao Tang. Overview of Organic Electrochemical Synthesis [J]. University Chemistry, 2025, 40(2): 210-215.
[11]	Wenxu Liu, Feng Han, Boxuan Wang, Huayi Liu, Xiaobin Gu, Xin Zhang, Yao Liu. Comprehensive Chemical Experiment: Design, Synthesis, and Photoelectronic Properties Study of Fully Non-Fused Ring Electron Acceptors [J]. University Chemistry, 2025, 40(10): 263-275.
[12]	Yuji Liu, Yuntian Zhang, Xu Jia, Zhiwei Zeng, Shupeng Zhang, Wei Dong, Yongxing Tang. Preparation of N―N Coupling Compounds via Nitrogen-Centered Radical Reaction [J]. University Chemistry, 2025, 40(1): 318-323.
[13]	Ruiyuan Xu, Yuxin Wang, Yuru Zhang, Wanmei Li. Who Destroyed Snowflake Castle [J]. University Chemistry, 2024, 39(9): 224-228.
[14]	Yiming Lu, Xiang Xie, Xiaoqing Qiu, Yang Liu, Xinyuan Cheng. The New Year’s Eve of the Aviation Brake Material Family [J]. University Chemistry, 2024, 39(9): 203-207.
[15]	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 [J]. University Chemistry, 2024, 39(8): 324-330.

Research Progress of Asymmetric C―H/C―H Cross Dehydrogenation Coupling Reaction

RichHTML

PDF

Like

Knowledge

Abstract

Cite this article

share this article

Figures/Tables 29

References 44

Related Articles 15

Metrics

Recommended 0