基于烯烃碳-氢键活化的碳-碳交叉偶联反应

doi:10.3866/PKU.DXHX202306052

Abstract

Abstract:

Olefins are a very important class of compounds, which can be transformed to various complex organic molecules through a series of transformations. In this paper, C—C cross coupling reaction based on olefinic C—H bond activation is described in detail. Based on the activation of C—H bonds, C—C bonds are constructed through C—C cross coupling reaction by transition metal catalysts such as Rh, Pd and Co. This introduction of olefinic C—H bond activation can enrich and expand the knowledge of olefins in organic chemistry courses, and it is also helpful for students to understand the forefront of organic chemistry development, stimulate their learning enthusiasm and initiative, and cultivate their scientific research literacy.

Key words: Transition metal catalysis, C—H bond activation, Olefins, Coupling reaction

Rui Yan, Hu Chen, Ming Zhao. C—C Cross Coupling Reaction Based on Olefinic C—H Bond Activation[J].University Chemistry, 2024, 39(1): 87-94.

Figures/Tables 13

References 26

27	Kim M. ; Han S. H. ; Kim I. S. Chem. Commun. 2014, 50, 11303. doi: 10.1039/C4CC03354J
28	Wu X. ; Ji H. Org. Chem. 2018, 83, 12094. doi: 10.1021/acs.joc.7b02481
1	邢其毅; 裴伟伟; 徐瑞秋; 裴坚. 基础有机化学(上册), 第4版北京: 北京大学出版社, 2016, 341- 350.
2	Sigman M. S. ; Werner E. W. Acc. Chem. Res. 2012, 45, 874. doi: 10.1021/ar200236v
3	Colby D. A. ; Bergman R. G. ; Ellman J. A. Chem. Rev. 2010, 110, 624. doi: 10.1021/cr900005n
4	Colby D. A. ; Tsai A. S. ; Bergman R. G. ; Ellman J. A. Acc. Chem. Res. 2012, 45, 814. doi: 10.1021/ar200190g
5	Gung B. W. ; Kumi G.J. Org. Chem. 2004, 69, 3488. doi: 10.1021/jo049920g
6	Fontana A. ; d'lppolito G. ; D'Souza L. ; Mollo E. ; Parameswaram P. S. ; Cimino G.J. Nat. Prod. 2001, 64, 131. doi: 10.1021/np0002435
7	Kong J. R. ; Ngai M. Y. ; Krische M. J.J. Am. Chem. Soc. 2006, 128, 718. doi: 10.1021/ja056474l
8	Miller K. M. ; Luanphaisarnnont T. ; Molinaro C. ; Jamison T. F J. Am. Chem. Soc. 2004, 126, 4130. doi: 10.1021/ja0491735
9	Finkbeiner P. ; Kloeckner U. ; Nachtsheim B. J. Angew. Chem. Int. Ed. 2015, 54, 4949. doi: 10.1002/anie.201412148
10	Caspers L. D. ; Finkbeiner P. ; Nachtsheim B. J. Chem. Eur. J. 2017, 23, 2748. doi: 10.1002/chem.201606026
11	Feng C. ; Feng D. ; Luo Y. ; Loh T. P. Org. Lett. 2014, 16, 5956. doi: 10.1021/ol502984g
12	Xu Y. ; Zhang Q. ; He T. ; Meng F. ; Loh T. P. Adv. Synth. Catal. 2014, 356, 1539. doi: 10.1002/adsc.201400171
13	Negishi E. Angew. Chem. Int. Ed. 2011, 50, 6738. doi: 10.1002/anie.201101380
14	Kuttruff C. A. ; Geiger S. ; Cakmak M. ; Mayer P. ; Trauner D. Org. Lett. 2012, 14, 1070. doi: 10.1021/ol203437a
15	Hubert P. ; Seibel E. ; Beemelmanns C. ; Campagne J.-M. ; Figueiredo R. M. Adv. Synth. Catal. 2020, 362, 5532. doi: 10.1002/adsc.202000730
16	Soengas R. G. ; Rodríguez-Solla H. Molecules 2021, 26, 249. doi: 10.3390/molecules26020249
17	Wen Z.-K. ; Xu Y.-H. ; Loh T.-P. Chem. Sci. 2013, 4, 4520. doi: 10.1039/c3sc52275j
18	Zhong X.-M. ; Cheng G.-J. ; Chen P. ; Zhang X. ; Wu Y.-D. Org. Lett. 2016, 18, 5240. doi: 10.1021/acs.orglett.6b02542
19	Zhang X. ; Wang M. ; Zhang M.-X. ; Xu Y.-H. ; Loh T.-P. Org. Lett. 2013, 15, 5531. doi: 10.1021/ol402692t
20	Xu Y.-H. ; Lu J. ; Loh T.-P. J. Am. Chem. Soc. 2009, 131, 1372. doi: 10.1021/ja8084548
21	Xu Y.-H. ; Wang W.-J. ; Wen Z.-K. ; Hartley J. J. ; Loh T.-P. Tetrahedron Lett. 2010, 51, 3504. doi: 10.1016/j.tetlet.2010.04.097
22	Zhang Y. ; Cui Z. ; Li Z. ; Liu Z.-Q. Org. Lett. 2012, 14, 1838. doi: 10.1021/ol300442w
23	Boultadakis-Arapinis M. ; Hopkinson M. N. ; Glorius F. Org. Lett. 2014, 16, 1630. doi: 10.1021/ol500258q
24	Liang Q.-J. ; Yang C. ; Meng F.-F. ; Jiang B. ; Xu Y.-H. ; Loh T.-P. Angew. Chem. Int. Ed. 2017, 56, 5091. doi: 10.1002/anie.201700559
25	Misha N. K. ; Sharma S. ; Park J. ; Han S. ; Kim I. S.. ACS Catal. 2017, 7, 2821. doi: 10.1021/acscatal.7b00159
26	Gensch T. ; Vásquez-Céspedes S. ; Yu D.-G. ; Glorius F. Org. Lett. 2015, 17, 3714. doi: 10.1021/acs.orglett.5b01701

[1]	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 [J]. University Chemistry, 2025, 40(7): 267-276.
[2]	Yan Li, Xinze Wang, Xue Yao, Shouyun Yu. Kinetic Resolution Enabled by Photoexcited Chiral Copper Complex-Mediated Alkene E→Z Isomerization: A Comprehensive Chemistry Experiment for Undergraduate Students [J]. University Chemistry, 2024, 39(5): 1-10.
[3]	Xinwei Hu, Zhixiong Ruan. Benzylic C―H Azolation of p-Ethyl Anisole by Electro-Oxidation [J]. University Chemistry, 2023, 38(9): 263-271.
[4]	Jing Cheng, Xueping Yang, Jian Jin, Peng Ren. An Experimental Teaching Design for Learning Hammett Equation Using Suzuki Coupling Reaction [J]. University Chemistry, 2023, 38(9): 272-279.
[5]	Yize Xu, Renjia Zhang, Ruopu Li, Jian Zhou, Dazhen Xu. Sharing of Experience from the Perspective of Students: How to Realize the Development from Basic Chemistry Courses to Undergraduate Scientific Research Innovation [J]. University Chemistry, 2023, 38(2): 289-298.
[6]	Yiming Li, Benhua Wang, Baosheng Wei, Xiangzhi Song, Yiming Luo, Guipeng Yu. Design, Multi-Path Synthesis and Characterization of Stellate Polyschiff Base: A Chemistry Scientific Training Experiment [J]. University Chemistry, 2023, 38(12): 61-66.
[7]	Ruopu Li, Yize Xu, Renming Hu, Yihuan Lai, Dazhen Xu. Application of "Iron Salt + Air" Catalytic Oxidation System in Green Cross Coupling Reaction: Recommendation for an Undergraduate Research-Training Program [J]. University Chemistry, 2023, 38(1): 295-303.
[8]	Di Zhang, Tian Xia, Yongxiang Luo, Xi Wang. Visible-Light-Driven Biomimetic Catalytic Green Synthesis and Quantitative Analysis of Coumarin Derivatives Based on Spectrophotometry [J]. University Chemistry, 2022, 37(5): 2111090-.
[9]	Zhi Wang, Qifei Shen, Yu Zhou, Bo Zhao, Duo Xi, Donfeng Dang. Synthesis and Characterization of Donor-Acceptor Typed Aggregation-Induced Emission (AIE) Luminogen Containing Triarylamine and Pyrazine [J]. University Chemistry, 2022, 37(2): 2110016-.
[10]	Yanyan Wang, Lingxiang Gao, Weiqiang Zhang, Quan Gu, Yajun Jian, Ziwei Gao. Integrating Green Chemistry into Teaching Laboratories: A Teaching Research on Green Suzuki-Miyaura Cross-Coupling Reaction [J]. University Chemistry, 2022, 37(12): 2112020-0.
[11]	Jiukai Xiong, Meijuan Zhao, Yanan Wang, Gang Bian, Ruixue Rong, Kerang Wang. Innovative Experiment for Students Based on Nobel Prizes in Chemistry: Construction of Fluorescent DPP Derivative by Suzuki Reaction [J]. University Chemistry, 2020, 35(12): 227-232.
[12]	Wei-Wei FU,Qing YI,Xia JIN,Xiang KUANG,Zi-Qing TANG. Synthesis of 4'-[5-(4-Carboxylphenylfuran)-2-yl)]-2, 2':6', 2"-Terpyridine: A Proposed Organic Chemistry Experiment [J]. University Chemistry, 2017, 32(6): 82-85.
[13]	Tian LI,Kai-Guo MA,Zhen GAO,Wei-Hong LI. A Brief Introduction to Suzuki-Miyaura Coupling Reaction in Organic Lab Abroad [J]. University Chemistry, 2016, 31(10): 98-104.
[14]	Dai Yazhong, Pei Jian. Mechanisms of Two Reduction Reactions under the Condition of Alkali Metal in Liquid Ammonia [J]. University Chemistry, 2015, 30(4): 58-62.

C—C Cross Coupling Reaction Based on Olefinic C—H Bond Activation

RichHTML

PDF

Like

Knowledge

Abstract

Cite this article

share this article

Figures/Tables 13

References 26

Related Articles 14

Metrics

Recommended 0