Citation:
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.
doi:
10.3866/PKU.DXHX202305034
-
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.
-
-
-
[1]
Li, C. J. Acc. Chem. Res. 2009, 42, 335.
-
[2]
Huang, Y. T.; Chen, Q. Chin. J. Org. Chem. 2021, 41, 4138.
-
[3]
Prakash, T. P.; Roman, M.; Bimal, K. B. Chem. Asian J. 2019, 14, 6.
-
[4]
Begur, V. V.; Jayaraman, D.; Kiran, R. B.; Yogesh, S.; Kaliyamoorthy, A.; Kandikere, R. P. Tetrahedron Lett. 2017, 58, 803.
-
[5]
Simon, A. G.; Thomas, K.; Li, C. J. Angew. Chem. Int. Ed. 2014, 53, 74.
-
[6]
Li, C. J. Chin. J. Chem. 2022, 40, 838.
-
[7]
Martin, K.; Devarajulu, S. Synthesis 2011, 3, 353.
-
[8]
Li, C. J.; Li, Z. P. Pure Appl. Chem. 2006, 78, 935.
-
[9]
Tian, T.; Li, Z. P.; Li, C. J. Green Chem. 2021, 23, 6789.
-
[10]
Caroline, J. S. Chem. Asian J. 2010, 5, 436.
-
[11]
Sun, C. L.; Li, B. J.; Shi, Z. J. Chem. Rev. 2011, 111, 1293.
-
[12]
Charles, S. Y.; Vy, M. D. Chem. Rev. 2011, 111, 1215.
-
[13]
Naeem, G.; Bertrand, S.; Martin, K. Catal. Sci. Technol. 2014, 4, 2778.
-
[14]
Ana, M. F. P.; Armando, J. L. P. ChemCatChem 2018, 10, 3354.
-
[15]
Zhang, Y.; Feng, B. N. Chin. J. Org. Chem. 2014, 34, 2406.
-
[16]
Cheng, M. X.; Yang, S. D. Synlett 2017, 28, 159.
-
[17]
Shikha, G. Org. Biomol. Chem. 2019, 17, 9683.
-
[18]
James, A. A. Chem. Soc. Rev. 2010, 39, 540.
-
[19]
Chrzanowska, M.; Grajewska, A.; Rozwadowska, M. D. Chem. Rev. 2016, 116, 12369.
-
[20]
Liu, W.; Liu, S.; Jin, R.; Guo, H.; Zhao, J. Org. Chem. Front. 2015, 2, 288.
-
[21]
Li, Z. P.; Li, C. J. Org. Lett. 2004, 6, 4997.
-
[22]
Li, Z. P.; Patricia, D. M.; Li, C. J. Tetrahedron-Asymmetry 2006, 17, 590.
-
[23]
Yu, J. B.; Li, Z. H.; Jia, K. Y.; Jiang, Z. J.; Liu, M. L.; Su, W. K. Tetrahedron Lett. 2013, 54, 2006.
-
[24]
Perepichka, I.; Kundu, S.; Hearne, Z.; Li, C. J. Org. Biomol. Chem. 2015, 13, 447.
-
[25]
Sun, S. T.; Li, C. K.; Paul, E. F.; Lou, H. X.; Liu, L. Org. Lett. 2015, 17, 1684.
-
[26]
Xie, Z. Y.; Liu, X. G.; Liu, L. Org. Lett. 2016, 18, 2982.
-
[27]
Huang, T. Y.; Liu, X. H.; Lang, J. W.; Xu, J.; Lin, L. L.; Feng, X. M. ACS Catal. 2017, 7, 5654.
-
[28]
Gaurav, K.; Shailesh, V.; Amamudin, A.; Rukhsana, I. K. Catal. Commun. 2017, 99, 94.
-
[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.
-
[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.
-
[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.
-
[34]
Zhang, G.; Ma, Y. X.; Wang, S. L.; Kong, W. D.; Wang, R. Chem. Sci. 2013, 4, 2645.
-
[35]
Tan, Y. Q.; Yuan, W.; Gong, L.; Eric, M. Angew. Chem. Int. Ed. 2015, 54, 13045.
-
[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.
-
[38]
Yang, X. R.; Xie, Z. X.; Li, Y.; Zhang, Y. Chem. Sci. 2020, 11, 4741.
-
[39]
Yu, J. B.; Ying, P.; Wang, H.; Xiang, K. Y.; Su, W. K. Adv. Synth. Catal. 2020, 362, 893.
-
[40]
Liu, X. G.; Zhao, C. Y.; Zhu, R. X.; Liu, L. Angew. Chem. Int. Ed. 2021, 60, 18499.
-
[41]
Hiromichi, E.; Kenji, M.; Takuya, O.; Takashi K.; Tsutomu, K. J. Am. Chem. Soc. 2010, 132, 13633.
-
[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.
-
[43]
Pan, X. G.; Wang, Z. H.; Kan, L. L.; Mao, Y.; Zhu, Y. S.; Liu, L. Chem. Sci. 2020, 11, 2414.
-
[44]
Wang, Z. H.; Zhu, Y. S.; Pan, X. G.; Wang, G.; Liu, L. Angew. Chem. Int. Ed. 2020, 59, 3053.
-
[1]
-
-
-
[1]
Ke QIAO , Yanlin LI , Shengli HUANG , Guoyu YANG . Advancements in asymmetric catalysis employing chiral iridium (ruthenium) complexes. Chinese Journal of Inorganic Chemistry, 2024, 40(11): 2091-2104. doi: 10.11862/CJIC.20240265
-
[2]
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. University Chemistry, 2024, 39(4): 75-80. doi: 10.3866/PKU.DXHX202311011
-
[3]
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
-
[4]
Danqing Wu , Jiajun Liu , Tianyu Li , Dazhen Xu , Zhiwei Miao . Research Progress on the Simultaneous Construction of C—O and C—X Bonds via 1,2-Difunctionalization of Olefins through Radical Pathways. University Chemistry, 2024, 39(11): 146-157. doi: 10.12461/PKU.DXHX202403087
-
[5]
Hong Lu , Yidie Zhai , Xingxing Cheng , Yujia Gao , Qing Wei , Hao Wei . Advancements and Expansions in the Proline-Catalyzed Asymmetric Aldol Reaction. University Chemistry, 2024, 39(5): 154-162. doi: 10.3866/PKU.DXHX202310074
-
[6]
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
-
[7]
Yuyang Xu , Ruying Yang , Yanzhe Zhang , Yandong Liu , Keyi Li , Zehui Wei . Research Progress of Aflatoxins Removal by Modern Optical Methods. University Chemistry, 2024, 39(11): 174-181. doi: 10.12461/PKU.DXHX202402064
-
[8]
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
-
[9]
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
-
[10]
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
-
[11]
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
-
[12]
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
-
[13]
Zihan Lin , Wanzhen Lin , Fa-Jie Chen . Electrochemical Modifications of Native Peptides. University Chemistry, 2025, 40(3): 318-327. doi: 10.12461/PKU.DXHX202406089
-
[14]
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
-
[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. University Chemistry, 2024, 39(8): 324-330. doi: 10.3866/PKU.DXHX202401063
-
[16]
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
-
[17]
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
-
[18]
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
-
[19]
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
-
[20]
Yiming Lu , Xiang Xie , Xiaoqing Qiu , Yang Liu , Xinyuan Cheng . The New Year’s Eve of the Aviation Brake Material Family. University Chemistry, 2024, 39(9): 203-207. doi: 10.12461/PKU.DXHX202403061
-
[1]
Metrics
- PDF Downloads(1)
- Abstract views(670)
- HTML views(92)