Bromopalladation Triggering the Cascade Oxidative Heterocyclization Reaction of Alkynes with Alkenes in Ionic Liquids
- Corresponding author: Yang Shaorong, lisryang@scut.edu.cn
Citation:
An Yanni, Li Jianxiao, Zhang Zhenming, Li Chunsheng, Yang Shaorong. Bromopalladation Triggering the Cascade Oxidative Heterocyclization Reaction of Alkynes with Alkenes in Ionic Liquids[J]. Chinese Journal of Organic Chemistry,
;2016, 36(9): 2136-2141.
doi:
10.6023/cjoc201603043
Eftekhari-Sis, B.; Zirak, M.; Akbari, A.Chem.Rev.2013, 113, 2958.
(b) Luo, P.; Tang, R.; Zhong, P.; Li, J.Chin.J.Org.Chem.2009, 29, 1924(in Chinese).
(罗培松, 汤日元, 钟平, 李金恒, 有机化学, 2009, 29, 1924.)
Chen, J.-R.; Hu, X.-Q.; Lu, L.-Q.; Xiao, W.-J.Chem.Rev.2015, 115, 5301.
(b) Huang, H.; Ji, X.; Wu, W.; Jiang, H.Chem.Soc.Rev.2015, 44, 1155.
Yang, L.; Huang, H.Chem.Rev.2015, 115, 3468.
(b) Yamamoto, Y.Chem.Soc.Rev.2014, 43, 1575.
Wu, W.; Jiang, H.Acc.Chem.Res.2012, 45, 1736.
(b) Wu, W.; Jiang, H.Acc.Chem.Res.2014, 47, 2483.
Su, D.; Tang, W.; Hu, Y.; Liu, Y.; Yu, S.; Ma, S.; Qu, J.; Yu, D.J.Nat.Prod.2008, 71, 784.
(b) Chen, L.; Zhu, H.; Wang, R.; Zhou, K.; Jing, Y.; Qiu, F.J.Nat.Prod.2008, 71, 852.
Liu, G.; Lu, X.Tetrahedron Lett.2003, 44, 127.
(b) Son, S.; Fu, G.C.J.Am.Chem.Soc.2007, 129, 1046.
(c) Huang, L.; Jiang, H.; Qi, C.; Liu, X.J.Am.Chem.Soc.2010, 132, 17652.
(d) Huang, H.; Ji, X.; Wu, W.; Jiang, H.Chem.Commun.2013, 49, 3351.
(e) Oliveira, C.C.; Angnes, R.A.; Correia, C.R.D.J.Org.Chem.2013, 78, 4373.
Zhang, Q.; Xu, W.; Lu, X.J.Org.Chem.2005, 70, 1505.
doi: 10.1021/jo048414o
Wang, Z.; Lu, X.J.Org.Chem.1996, 61, 2254.
doi: 10.1021/jo9522466
Aurrecoechea, J.; Durana, A.; Pérez, E.J.Org.Chem.2008, 73, 3650.
doi: 10.1021/jo800211q
Martınez, C.; Álvarez, R.; Aurrecoechea, J.M.Org.Lett.2009, 11, 1083.
doi: 10.1021/ol8028687
Wolfe, J.P.; Rossi, M.J.Am.Chem.Soc.2004, 126, 1620.
(b) Nakhla, J.; Kampf, J.; Wolfe, J.P.J.Am.Chem.Soc.2006, 128, 2893.
(c) Lemen, G.S.; Giampietro, N.C.; Hay, M.B.; Wolfe, J.P.J.Org.Chem.2009, 74, 2533.
Huang, L.; Wang, Q.; Liu, X.; Jiang, H.Angew.Chem., Int.Ed.2012, 51, 5696.
doi: 10.1002/anie.201109141
Huang, L.; Wang, Q.; Wu, W.; Jiang, H.J.Org.Chem.2014, 79, 7734.
doi: 10.1021/jo501317v
Zhang, Z.; Ouyang, L.; Wu, W.; Li, J.; Zhang, Z.; Jiang, H.J.Org.Chem.2014, 79, 10734.
doi: 10.1021/jo501606c
Zhang, Z.; Wu, W.; Liao, J.; Li, J.; Jiang, H.Chem.Eur.J.2015, 21, 6708.
doi: 10.1002/chem.201500397
Li, J.; Yang, W.; Yang, S.; Huang, L.; Wu, W.; Sun, Y.; Jiang, H.Angew.Chem., Int.Ed.2014, 53, 7219.
doi: 10.1002/anie.201403341
Li, J.; Yang, S.; Jiang, H.; Wu, W.; Zhao, J.J.Org.Chem.2013, 78, 12477.
(b) Li, J.; Yang, S.Chin.J.Org.Chem.2013, 33, 2407(in Chinese).
(李建晓, 杨少容, 有机化学, 2013, 33, 2407.)
(c) Li, J.; Yang, S.; Wu, W.; Jiang, H.Chem.Commun.2014, 50, 1381.
(d) Li, J.; Li, C.; Yang, S.; Luo, W.Chin.J.Org.Chem.2015, 35, 898(in Chinese).
(李建晓, 李春生, 杨少容, 罗维, 有机化学, 2015, 35, 898.)
(e) Li, J.; Zhu, Z.; Yang, S.; Zhang, Z.; Wu, W.; Jiang, H.J.Org.Chem.2015, 80, 3870.
(f) Li, J.; Zhang, Z.; Li, C.; Luo, W.; Yang, S.Chin.J.Org.Chem.2015, 35, 2199(in Chinese).
(李建晓, 张振明, 李春生, 罗维, 杨少容, 有机化学, 2015, 35, 2199.)
Huddleston, J.G.; Willauer, H.D.; Swatloski, R.P.; Visser, A.E.; Rogers, R.D.Chem.Commun.1998, 1765.
Park, S.; Kazlauskas, R.J.J.Org.Chem.2001, 66, 8395.
doi: 10.1021/jo015761e
Branco, L.C.; Rosa, J.N.; Ramos, J.J.M.; Afonso, C.A.M.Chem.Eur.J.2002, 8, 3671.
doi: 10.1002/1521-3765(20020816)8:16<3671::AID-CHEM3671>3.0.CO;2-9
Miao, C.X.; He, L.N.; Wang, J.Q.; Wang, J.L.Adv.Synth.Catal.2009, 351, 2209.
doi: 10.1002/adsc.v351:13
Zhenxing Liu , Jiaen Hu , Zishi Cheng , Xinqi Hao . 基础有机化学教学中烯烃的氧化反应. University Chemistry, 2025, 40(6): 139-144. doi: 10.12461/PKU.DXHX202408107
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
Qiang Zhang , Yuanbiao Huang , Rong Cao . Imidazolium-Based Materials for CO2 Electroreduction. Acta Physico-Chimica Sinica, 2024, 40(4): 2306040-0. doi: 10.3866/PKU.WHXB202306040
Weihan Zhang , Menglu Wang , Ankang Jia , Wei Deng , Shuxing Bai . Surface Sulfur Species Influence Hydrogenation Performance of Palladium-Sulfur Nanosheets. Acta Physico-Chimica Sinica, 2024, 40(11): 2309043-0. doi: 10.3866/PKU.WHXB202309043
Yameen Ahmed , Xiangxiang Feng , Yuanji Gao , Yang Ding , Caoyu Long , Mustafa Haider , Hengyue Li , Zhuan Li , Shicheng Huang , Makhsud I. Saidaminov , Junliang Yang . Interface Modification by Ionic Liquid for Efficient and Stable FAPbI3 Perovskite Solar Cells. Acta Physico-Chimica Sinica, 2024, 40(6): 2303057-0. doi: 10.3866/PKU.WHXB202303057
Zihao Guo , Shichen Ma , Kin Shing Chan . 烯烃环化反应中6电子试剂的等瓣相似性和等电子关系. University Chemistry, 2025, 40(6): 160-166. doi: 10.12461/PKU.DXHX202408038
Yue Zhao , Yanfei Li , Tao Xiong . Copper Hydride-Catalyzed Nucleophilic Additions of Unsaturated Hydrocarbons to Aldehydes and Ketones. University Chemistry, 2024, 39(4): 280-285. doi: 10.3866/PKU.DXHX202309001
Renxiao Liang , Zhe Zhong , Zhangling Jin , Lijuan Shi , Yixia Jia . A Palladium/Chiral Phosphoric Acid Relay Catalysis for the One-Pot Three-Step Synthesis of Chiral Tetrahydroquinoline. University Chemistry, 2024, 39(5): 209-217. doi: 10.3866/PKU.DXHX202311024
Jiaxun Wu , Mingde Li , Li Dang . The R eaction of Metal Selenium Complexes with Olefins as a Tutorial Case Study for Analyzing Molecular Orbital Interaction Modes. University Chemistry, 2025, 40(3): 108-115. doi: 10.12461/PKU.DXHX202405098
Bolin Sun , Jie Chen , Ling Zhou . 乙烯型卤代烃的亲核取代反应. University Chemistry, 2025, 40(8): 152-157. doi: 10.12461/PKU.DXHX202410032
Wenjun Zheng . Application in Inorganic Synthesis of Ionic Liquids. University Chemistry, 2024, 39(8): 163-168. doi: 10.3866/PKU.DXHX202401020
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
Xudong Liu , Huili Fan , Junping Xiao , Min Yang , Yan Li . Teaching Approaches to the AE + AN Mechanism of Electrophilic Addition Reactions between Olefins and Inorganic Acids in Organic Chemistry. University Chemistry, 2025, 40(7): 367-372. doi: 10.12461/PKU.DXHX202409041
Xinghai Liu , Hongke Wu . Exploration and Practice of Ideological and Political Education in Heterocyclic Chemistry Based on "Fentanyl" Event. University Chemistry, 2024, 39(8): 359-364. doi: 10.3866/PKU.DXHX202312100
Yan Li , Xinze Wang , Xue Yao , Shouyun Yu . 基于激发态手性铜催化的烯烃E→Z异构的动力学拆分——推荐一个本科生综合化学实验. University Chemistry, 2024, 39(5): 1-10. doi: 10.3866/PKU.DXHX202309053
Xuejie Wang , Guoqing Cui , Congkai Wang , Yang Yang , Guiyuan Jiang , Chunming Xu . Research Progress on Carbon-based Catalysts for Catalytic Dehydrogenation of Liquid Organic Hydrogen Carriers. Acta Physico-Chimica Sinica, 2025, 41(5): 100044-0. doi: 10.1016/j.actphy.2024.100044
Zhengyu Zhou , Huiqin Yao , Youlin Wu , Teng Li , Noritatsu Tsubaki , Zhiliang Jin . Synergistic Effect of Cu-Graphdiyne/Transition Bimetallic Tungstate Formed S-Scheme Heterojunction for Enhanced Photocatalytic Hydrogen Evolution. Acta Physico-Chimica Sinica, 2024, 40(10): 2312010-0. doi: 10.3866/PKU.WHXB202312010
Haoyu Sun , Dun Li , Yuanyuan Min , Yingying Wang , Yanyun Ma , Yiqun Zheng , Hongwen Huang . Hierarchical Palladium-Copper-Silver Porous Nanoflowers as Efficient Electrocatalysts for CO2 Reduction to C2+ Products. Acta Physico-Chimica Sinica, 2024, 40(6): 2307007-0. doi: 10.3866/PKU.WHXB202307007
Wenjuan Tan , Yong Ye , Xiujuan Sun , Bei Liu , Jiajia Zhou , Hailong Liao , Xiulin Wu , Rui Ding , Enhui Liu , Ping Gao . Building P-Poor Ni2P and P-Rich CoP3 Heterojunction Structure with Cation Vacancy for Enhanced Electrocatalytic Hydrazine and Urea Oxidation. Acta Physico-Chimica Sinica, 2024, 40(6): 2306054-0. doi: 10.3866/PKU.WHXB202306054
Daojuan Cheng , Fang Fang . Exploration and Implementation of Science-Education Integration in Organic Chemistry Teaching for Pharmacy Majors: A Case Study on Nucleophilic Substitution Reactions of Alkyl Halides. University Chemistry, 2024, 39(11): 72-78. doi: 10.12461/PKU.DXHX202403105