Citation: Qiu Huihua, Cheng Borui, Huang Yingsi, Chen Cui, Zhou Peng. Research on the Tandem Reaction via Chloropalladation/Heck Cross Coupling of o-(Alkynyl)styrenes with Pd/O₂[J]. Chinese Journal of Organic Chemistry, ;2018, 38(7): 1817-1822. doi: 10.6023/cjoc201801030 shu

Research on the Tandem Reaction via Chloropalladation/Heck Cross Coupling of o-(Alkynyl)styrenes with Pd/O₂

School of Chemical Engineering, Guangdong University of Petrochemical Technology, Maoming 525000

Corresponding author: Qiu Huihua, qh198511@163.com
Received Date: 23 January 2018
Revised Date: 26 March 2018
Available Online: 12 July 2018
Fund Project: the National Natural Science Foundation of China 21602035Project supported by the National Natural Science Foundation of China (No. 21602035) and the Natural Science Foundation of Guangdong Province (No. 2016A030307030)the Natural Science Foundation of Guangdong Province 2016A030307030

Figures(2)

An economic and environmental synthestic method for 3-chloroindenes from o-(alkynyl)styrenes through tandem reactions including choropalladation/Heck cross coupling in Pd/O₂ system was reported. Taking green dioxygen as sole oxidant and LiCl as chlorine source, 13 functionalized 3-chloroindenes could be synthesized in moderate to high yield without the addition of CuCl₂
- Pd-catalyzed,
- dioxygen,
- chloropalladation,
- indene
1. [1]
  Selected review and examples on chloropalladation, please see: (a) Lu, X. In Handbook of Organopalladium Chemistry for Organic Synthesis, Ed. : Negishi, E., Wiley-Interscience, New York, 2002, Vol. 2, pp. 2267~2288.
  (b) Huang, L. ; Wang Q. ; Liu, X. ; Jiang, H. Angew. Chem., Int. Ed. 2012, 51, 5696.
  (c) Huang, L. ; Wang, Q. ; Wu, W. ; Jiang, H. J. Org. Chem. 2014, 79, 7734.
  (d) Zhang, Z. ; Ouyang, L. ; Wu, W. ; Li, J. ; Zhang, Z. ; Jiang, H. J. Org. Chem. 2014, 79, 10734.
  (e) Sun, N. ; Li, Y. ; Yin, G. ; Jiang, S. Eur. J. Org. Chem. 2013, 2541.
  (f) Zhang, Z. ; Wu, W. ; Liao, J. ; Li, J. ; Jiang, H. Chem. -Eur. J. 2015, 21, 6708.
  (g) Derosa, J. ; Cantu, A. L. ; Boulous, M. N. ; O'Duill, M. L. ; Turnbull, J. L. ; Liu, Z. ; Torre, D. L. T. ; Engle, K. M. J. Am. Chem. Soc. 2017, 139, 5183.
  (h) Li, J. ; Hu, W. ; Li, C. Yang, S. ; Wu, W. ; Jiang, H. Org. Chem. Front. 2017, 4, 373.
2. [2]
3. [3]
4. [4]
  For some selected examples, please see: (a) Citta, A. ; Folda, A. ; Bindoli, A. ; Pigeon, P. ; Top, S. ; Vessières, A. ; Salmain, M. ; Jaouen, G. ; Rigobello, M. P. J. Med. Chem. 2014, 57, 8849.
  (b) Tehfe, M. ; Dumur, F. ; Graff, B. ; Gigmes, D. ; Fouassier, J. ; Lalevée, J. Macromolecules 2013, 46, 3332.
  (c) Mróz, W. ; Villafiorita-Monteleone, F. ; Pasini, M. ; Grisci, G. ; Paolino, M. ; Razzano, V. ; Cappelli, A. ; Botta, C. Mater. Lett. 2015, 142, 197.
  (d) Guerlin, A. ; Dumur, F. ; Dumas, E. ; Miomandre, F. ; Wantz, G. C. ; Mayer, R. Org. Lett. 2010, 12, 2382.
5. [5]
  Selected examples, please see: (a) Mosslemin, M. H. ; Shams, N. ; Esteghamat, H. ; Anaraki-Ardakani, H. Chin. Chem. Lett. 2013, 24, 1095.
  (b) Zhou, F. ; Yang, M. ; Lu, X. Org. Lett. 2009, 11, 1405.
  (c) Bu, X. ; Hong, J. ; Zhou, X. Adv. Synth. Catal. 2011, 353, 2111.
  (d) Jia, X. ; Petrone, D. A. ; Lautens, M. Angew. Chem., Int. Ed. 2012, 51, 9870.
  (e) Zeng, Z. ; Ilies, L. ; Nakamura, E. J. Am. Chem. Soc. 2011, 133, 17638.
  (f) Huang, X. ; Yang, X. ; Song, R. ; Li, J. J. Org. Chem. 2014, 79, 1025.
6. [6]
  Ye, S.; Gao, K.; Zhou, H.; Yang X.; Wu, J. Chem. Commun. 2009, 5406.
7. [7]
  Zhou, P.; Liu, W.; Qiu, H. Chem. Lett. 2015, 44, 1637. doi: 10.1246/cl.150756
8. [8]
  (a) Shi, Z. ; Zhang, C. ; Li, S. ; Pan, D. Ding, S. ; Cui, Y. ; Jiao, N. Angew. Chem., Int. Ed. 2009, 48, 4572.
  (b) Lafrance, M. ; Fagnou, K. J. Am. Chem. Soc. 2006, 128, 16496.
9. [9]
  Zhou, F.; Han, X.; Lu, X. J. Org. Chem. 2011, 76, 1491. doi: 10.1021/jo1023574
1. [1]
  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
2. [2]
  Zhuoyan Lv , Yangming Ding , Leilei Kang , Lin Li , Xiao Yan Liu , Aiqin Wang , Tao Zhang . Light-Enhanced Direct Epoxidation of Propylene by Molecular Oxygen over CuO_x/TiO₂ Catalyst. Acta Physico-Chimica Sinica, 2025, 41(4): 2408015-0. doi: 10.3866/PKU.WHXB202408015
3. [3]
  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
4. [4]
  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
5. [5]
  Xue-Peng Zhang , Yuchi Long , Yushu Pan , Jiding Wang , Baoyu Bai , Rui Ding . 定量构效关系方法学习探索：以钴卟啉活化氧气为例. University Chemistry, 2025, 40(8): 345-359. doi: 10.12461/PKU.DXHX202410107
6. [6]
  Hongting Yan , Aili Feng , Rongxiu Zhu , Lei Liu , Dongju Zhang . Reexamination of the Iodine-Catalyzed Chlorination Reaction of Chlorobenzene Using Computational Chemistry Methods. University Chemistry, 2025, 40(3): 16-22. doi: 10.12461/PKU.DXHX202403010
7. [7]
  Guangming YIN , Huaiyao WANG , Jianhua ZHENG , Xinyue DONG , Jian LI , Yi'nan SUN , Yiming GAO , Bingbing WANG . Preparation and photocatalytic degradation performance of Ag/protonated g-C₃N₄ nanorod materials. Chinese Journal of Inorganic Chemistry, 2024, 40(8): 1491-1500. doi: 10.11862/CJIC.20240086
8. [8]
  Mengyang LI , Hao XU , Zhonghao NIU , Chunhua GONG , Weihui ZHONG , Jingli XIE . Highly effective catalytic synthesis of β-amino alcohols by using viologen-polyoxometalate hybrid materials. Chinese Journal of Inorganic Chemistry, 2025, 41(7): 1294-1300. doi: 10.11862/CJIC.20250080
9. [9]
  Yufang GAO , Nan HOU , Yaning LIANG , Ning LI , Yanting ZHANG , Zelong LI , Xiaofeng LI . Nano-thin layer MCM-22 zeolite: Synthesis and catalytic properties of trimethylbenzene isomerization reaction. Chinese Journal of Inorganic Chemistry, 2024, 40(6): 1079-1087. doi: 10.11862/CJIC.20240036
10. [10]
  Wenlong Wang , Wentao Hao , Lang He , Jia Qiao , Ning Li , Chaoqiu Chen , Yong Qin . Bandgap and adsorption engineering of carbon dots/TiO₂ S-scheme heterojunctions for enhanced photocatalytic CO₂ methanation. Acta Physico-Chimica Sinica, 2025, 41(9): 100116-0. doi: 10.1016/j.actphy.2025.100116
11. [11]
  Lina Guo , Ruizhe Li , Chuang Sun , Xiaoli Luo , Yiqiu Shi , Hong Yuan , Shuxin Ouyang , Tierui Zhang . Effect of Interlayer Anions in Layered Double Hydroxides on the Photothermocatalytic CO₂ Methanation of Derived Ni-Al₂O₃ Catalysts. Acta Physico-Chimica Sinica, 2025, 41(1): 100002-0. doi: 10.3866/PKU.WHXB202309002
12. [12]
  Dong Xiang , Kunzhen Li , Kanghua Miao , Ran Long , Yujie Xiong , Xiongwu Kang . Amine-Functionalized Copper Catalysts: Hydrogen Bonding Mediated Electrochemical CO₂ Reduction to C₂ Products and Superior Rechargeable Zn-CO₂ Battery Performance. Acta Physico-Chimica Sinica, 2024, 40(8): 2308027-0. doi: 10.3866/PKU.WHXB202308027
13. [13]
  Jiaqi AN , Yunle LIU , Jianxuan SHANG , Yan GUO , Ce LIU , Fanlong ZENG , Anyang LI , Wenyuan WANG . Reactivity of extremely bulky silylaminogermylene chloride and bonding analysis of a cubic tetragermylene. Chinese Journal of Inorganic Chemistry, 2024, 40(8): 1511-1518. doi: 10.11862/CJIC.20240072
14. [14]
  Yongpo Zhang , Xinfeng Li , Yafei Song , Mengyao Sun , Congcong Yin , Chunyan Gao , Jinzhong Zhao . Synthesis of Chlorine-Bridged Binuclear Cu(I) Complexes Based on Conjugation-Driven Cu(II) Oxidized Secondary Amines. University Chemistry, 2024, 39(5): 44-51. doi: 10.3866/PKU.DXHX202309092
15. [15]
  Jianan Zhang , Mengzhen Xu , Jiamin Liu , Yufei He . 面向“双碳”目标的脱氯吸附剂开发研究型综合实验设计. University Chemistry, 2025, 40(6): 248-255. doi: 10.12461/PKU.DXHX202408068
16. [16]
  Baitong Wei , Jinxin Guo , Xigong Liu , Rongxiu Zhu , Lei Liu . Theoretical Study on the Structure, Stability of Hydrocarbon Free Radicals and Selectivity of Alkane Chlorination Reaction. University Chemistry, 2025, 40(3): 402-407. doi: 10.12461/PKU.DXHX202406003
17. [17]
  Ruonan Li , Shijie Liang , Yunhua Xu , Cuifen Zhang , Zheng Tang , Baiqiao Liu , Weiwei Li . Chlorine-Substituted Double-Cable Conjugated Polymers with Near-Infrared Absorption for Low Energy Loss Single-Component Organic Solar Cells. Acta Physico-Chimica Sinica, 2024, 40(8): 2307037-0. doi: 10.3866/PKU.WHXB202307037
18. [18]
  Jizhou Liu , Chenbin Ai , Chenrui Hu , Bei Cheng , Jianjun Zhang . Accelerated Interfacial Electron Transfer in Perovskite Solar Cell by Ammonium Hexachlorostannate Modification and fs-TAS Investigation. Acta Physico-Chimica Sinica, 2024, 40(11): 2402006-0. doi: 10.3866/PKU.WHXB202402006
19. [19]
  Hongsheng Tang , Yonghe Zhang , Dexiang Wang , Xiaohui Ning , Tianlong Zhang , Yan Li , Hua Li . A Wonderful Journey through the Kingdom of Hazardous Chemicals. University Chemistry, 2024, 39(9): 196-202. doi: 10.12461/PKU.DXHX202403098
20. [20]
  Shiyan Cheng , Yonghong Ruan , Lei Gong , Yumei Lin . Research Advances in Friedel-Crafts Alkylation Reaction. University Chemistry, 2024, 39(10): 408-415. doi: 10.12461/PKU.DXHX202403024

Get Citation

PDF

XML

Metrics

PDF Downloads(3)
Abstract views(764)
HTML views(82)

通讯作者: 陈斌, bchen63@163.com

1.
沈阳化工大学材料科学与工程学院沈阳 110142

Research on the Tandem Reaction via Chloropalladation/Heck Cross Coupling of o-(Alkynyl)styrenes with Pd/O2

Metrics

通讯作者: 陈斌, bchen63@163.com

Research on the Tandem Reaction via Chloropalladation/Heck Cross Coupling of o-(Alkynyl)styrenes with Pd/O₂