Citation: Tang Xiaoqi, Xie Libo, Chen Yali, Tian Ping, Lin Guoqiang. Recent Progress on Cu-Catalyzed Conjugate Silylation to Unsaturated Compounds[J]. Chinese Journal of Organic Chemistry, ;2016, 36(9): 2011-2023. doi: 10.6023/cjoc201605004 shu

Recent Progress on Cu-Catalyzed Conjugate Silylation to Unsaturated Compounds

Tang Xiaoqi ^a,b ,
Xie Libo ^b ,
Chen Yali ^a,*,, ,
Tian Ping ^b,*,, ,
Lin Guoqiang ^b

a.
Department of Chemistry, Shanghai University, Shanghai 200444
b.
CAS Key Laboratory of Synthetic Chemistry of Natural Substances, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032

Corresponding author: Chen Yali, ylchen@staff.shu.edu.cn Tian Ping, tianping@sioc.ac.cn
Received Date: 4 May 2016
Revised Date: 23 May 2016

Fund Project: the National Natural Science Foundation of China 21372243the National Natural Science Foundation of China 21572253the National Natural Science Foundation of China 21572251

Figures(24)

Organosilicon compounds have a wide range of applications in organic synthesis. It can be readily converted to a series of functional compounds through a simple operation. In the recent years, copper-catalyzed conjugate silylation of unsaturated compounds has emerged as a novel synthetic tool to introduce a variety of organosilicon compounds. Herein, this research progress, especially the development in the asymmetric conjugate silylation is summarized.
- copper,
- unsaturated compounds,
- asymmetric,
- conjugate silylation
1. [1]
  Denmark, S. E.; Liu, J. H.-C. Angew. Chem., Int. Ed. 2010, 49, 2978.
  (b) Hatanaka, Y.; Hiyama, T. J. Org. Chem. 1988, 53, 918.
  (c) Mori, A.; Danda, Y.; Fujii, T.; Hirabayashi, K.; Osakada, K. J. Am. Chem. Soc. 2001, 123, 10774.
  (d) Denmark, S. E.; Kallemeyn, J. M. J. Am. Chem. Soc. 2006, 128, 15958.
  (e) Koike, T.; Du, X.; Sanada, T.; Danda, Y.; Mori, A. Angew. Chem., Int. Ed. 2003, 42, 89.
  (f) Lu, M.-Z.; Lu, P.; Xu, Y.-H.; Loh, T.-P. Org. Lett. 2014, 16, 2614.
2. [2]
  Tamao, K.; Ishida, N.; Tanaka T.; Kumada, M. Organo-metallics 1983, 2, 1694.
  (b) Fleming, I.; Barbero, A.; Walter, D. Chem. Rev. 1997, 97, 2063.
  (c) Fleming, I.; Henning, R.; Plaut, H. J. Chem. Soc., Chem. Commun. 1984, 29.
3. [3]
  Ilardi, E. A.; Stivala, C. E.; Zakarian, A. Org. Lett. 2008, 10, 1727. doi: 10.1021/ol800341z
4. [4]
  Weickgenannt, A.; Oestreich, M. Chem. Eur. J. 2010, 16, 402.
  (b) Oestreich, M.; Hartmann, E.; Mewald, M. Chem. Rev. 2013, 113, 402.
  (c) Wang, H.; Yang, D.-Q.; MO, H.-H. Chin. J. Org. Chem. 2007, 27, 806(in Chinese)
  (王欢, 杨定乔, 莫海洪, 有机化学, 2007, 27, 806.)
5. [5]
  Qiu, H.-Y.; Lai, G.-Q. Chin. J. Org. Chem. 2007, 27, 806(in Chinese).
6. [6]
  Hengge E.; Holtschmidt, N. J. Organomet. Chem. 1968, 12, 5. doi: 10.1016/S0022-328X(00)90890-8
7. [7]
  Still, W. C. J. Org. Chem. 1976, 41, 3063. doi: 10.1021/jo00880a044
8. [8]
  Ager, D. J.; Fleming, I. J. Chem. Soc., Chem. Commun. 1978, 177.
  (b) Ager, D. J.; Fleming, I.; Patel, S. K. J. Chem. Soc., Perkin Trans. 11981, 2520.
  (c) Fleming, I.; Roessler, F. J. Chem. Soc., Chem. Commun. 1980, 276.
9. [9]
  Fleming, I.; Newton, T. W. J. Chem. Soc., Perkin Trans. 11984, 1805.
10. [10]
  Sharma, S.; Oehlschlager, A. C. Tetrahedron 1989, 45, 557;
  (b) Koreeda, M.; Koo, S. Tetrahedron Lett. 1990, 31, 831.
11. [11]
  Tückmantel, W.; Oshima, K.; Nozaki, H. Chem. Ber. 1986, 119, 1581.
  (b) Crump, R. A. N. C.; Fleming, I.; Urch, C. J. J. Chem. Soc., Perkin Trans. 11994, 701.
  (c) Vaughan, A.; Singer, R. D. Tetrahedron Lett. 1995, 36, 5683.
12. [12]
  Lipshutz, B. H.; Sclafani, J. A.; Takanami, T. J. Am. Chem. Soc. 1998, 120, 4021. doi: 10.1021/ja980152i
13. [13]
  Ito, H.; Ishizuka, T.; Tateiwa, J.; Sonoda, M.; Hosomi, A. J. Am. Chem. Soc. 1998, 120, 11196. doi: 10.1021/ja9822557
14. [14]
  Tamao, K.; Okazaki, S.; Kumada, M. J. Organomet. Chem. 1978, 146, 87.
  (b) Hayashi, T.; Matsumoto, Y.; Ito, Y. J. Am. Chem. Soc. 1988, 110, 5579.
15. [15]
  Dervan, P. B.; Shippey, M. A. J. Am. Chem. Soc. 1976, 98, 1265.
  (b) Ito, Y.; Suginome, M.; Murakami, M. J. Org. Chem. 1991, 56, 1948.
  (c) Yamashita, H.; Reddy, N. P.; Tanaka, M. Macromolecules 1993, 26, 2143.
  (d) Obora, Y.; Tsuji, Y.; Kawamura, T. J. Am. Chem. Soc. 1995, 117, 9814.
16. [16]
  Clark, C. T.; Lake, J. F.; Scheidt, K. A. J. Am. Chem. Soc. 2004, 126, 84. doi: 10.1021/ja038530t
17. [17]
  Lee, K.; Hoveyda, A. H. J. Am. Chem. Soc. 2010, 132, 2898 doi: 10.1021/ja910989n
18. [18]
  Matsumoto, Y.; Hayashi, T.; Ito, Y. Tetrahedron 1994, 50, 335.
  (b) Walter, C.; Auer, G.; Oestreich, M. Angew. Chem., Int. Ed. 2006, 45, 5675.
  (c) Walter, C.; Oestreich, M. Angew. Chem., Int. Ed. 2008, 47, 3818.
  (d) Walter, C.; Fröhlich, R.; Oestreich, M. Tetrahedron 2009, 65, 5513.
19. [19]
  Welle, A.; Petrignet, J.; Tinant, B.; Wouters, J.; Riant, O. Chem. Eur. J. 2010, 16, 10980. doi: 10.1002/chem.v16:36
20. [20]
  Ibrahem, I.; Santoro, S.; Himo, F.; Córdova, A. Adv. Synth. Catal. 2011, 353, 245. doi: 10.1002/adsc.201000908
21. [21]
  Calderone, J. A.; Santos, W. L. Org. Lett. 2012, 14, 2090. doi: 10.1021/ol300618j
22. [22]
  Iannazzo, L.; Molander, G. A. Eur. J. Org. Chem. 2012, 16, 4923.
23. [23]
  Pace, V.; Rae, J. P.; Harb, H. Y.; Procter, D. J. Chem. Commun. 2013, 49, 5150. doi: 10.1039/c3cc42160k
24. [24]
  Pace, V.; Rae, J. P.; Procter, D. J. Org. Lett. 2014, 16, 476. doi: 10.1021/ol4033623
25. [25]
  Plotzitzka, J.; Kleeberg, C. Organometallics 2014, 33, 6915. doi: 10.1021/om500989w
26. [26]
  Calderone, J. A.; Santos, W. L. Angew. Chem., Int. Ed. 2014, 53, 4154. doi: 10.1002/anie.201310695
27. [27]
  Kitanosono, T.; Zhu, L.; Liu, C.; Xu, P.; Kobayashi, S. J. Am. Chem. Soc. 2015, 137, 15422. doi: 10.1021/jacs.5b11418
28. [28]
  Lee, K.; Wu, H.; Haeffner, F.; Hoveyda, A. H. Organometallics 2012, 31, 7823. doi: 10.1021/om300790t
29. [29]
  López, A.; Parra, A.; Carlos, J.-B. Tortosa, M. Chem. Commun. 2015, 51, 17684. doi: 10.1039/C5CC06653K
30. [30]
  Wang, M.; Liu, Z.-L.; Zhang, X.; Tian, P.-P.; Xu, Y.-H.; Loh, T.-P. J. Am. Chem. Soc. 2015, 137, 14830. (Lu, Y.) doi: 10.1021/jacs.5b08279
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. [2]
  Qianwen Han , Tenglong Zhu , Qiuqiu Lü , Mahong Yu , Qin Zhong . 氢电极支撑可逆固体氧化物电池性能及电化学不对称性优化. Acta Physico-Chimica Sinica, 2025, 41(1): 2309037-. doi: 10.3866/PKU.WHXB202309037
3. [3]
  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
4. [4]
  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
5. [5]
  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. University Chemistry, 2025, 40(7): 267-276. doi: 10.12461/PKU.DXHX202408004
6. [6]
  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
7. [7]
  Dan Liu . 可见光-有机小分子协同催化的不对称自由基反应研究进展. University Chemistry, 2025, 40(6): 118-128. doi: 10.12461/PKU.DXHX202408101
8. [8]
  Ji Qi , Jianan Zhu , Yanxu Zhang , Jiahao Yang , Chunting Zhang . Visible Color Change of Copper (II) Complexes in Reversible SCSC Transformation: The Effect of Structure on Color. University Chemistry, 2024, 39(3): 43-57. doi: 10.3866/PKU.DXHX202307050
9. [9]
  Cheng Zheng , Shiying Zheng , Yanping Zhang , Shoutian Zheng , Qiaohua Wei . Synthesis, Copper Content Analysis, and Luminescent Performance Study of Binuclear Copper (I) Complexes with Isomeric Luminescence Shift: A Comprehensive Chemical Experiment Recommendation. University Chemistry, 2024, 39(7): 322-329. doi: 10.3866/PKU.DXHX202310131
10. [10]
  Hao Wu , Zhen Liu , Dachang Bai . ¹H NMR Spectrum of Amide Compounds. University Chemistry, 2024, 39(3): 231-238. doi: 10.3866/PKU.DXHX202309020
11. [11]
  Qianlang Wang , Jijun Sun , Qian Chen , Quanqin Zhao , Baojuan Xi . The Appeal of Organophosphorus Compounds: Clearing Their Name. University Chemistry, 2025, 40(4): 299-306. doi: 10.12461/PKU.DXHX202405205
12. [12]
  Qin Hou , Jiayi Hou , Aiju Shi , Xingliang Xu , Yuanhong Zhang , Yijing Li , Juying Hou , Yanfang Wang . Preparation of Cuprous Iodide Coordination Polymer and Fluorescent Detection of Nitrite: A Comprehensive Chemical Design Experiment. University Chemistry, 2024, 39(8): 221-229. doi: 10.3866/PKU.DXHX202312056
13. [13]
  Chi Li , Jichao Wan , Qiyu Long , Hui Lv , Ying Xiong . N-Heterocyclic Carbene (NHC)-Catalyzed Amidation of Aldehydes with Nitroso Compounds. University Chemistry, 2024, 39(5): 388-395. doi: 10.3866/PKU.DXHX202312016
14. [14]
  Ying Xiong , Guangao Yu , Lin Wu , Qingwen Liu , Houjin Li , Shuanglian Cai , Zhanxiang Liu , Xingwen Sun , Yuan Zheng , Jie Han , Xin Du , Chengshan Yuan , Qihan Zhang , Jianrong Zhang , Shuyong Zhang . Basic Operations and Specification Suggestions for Determination of Physical Constants of Organic Compounds. University Chemistry, 2025, 40(5): 106-121. doi: 10.12461/PKU.DXHX202503079
15. [15]
  Yongjian Zhang , Fangling Gao , Hong Yan , Keyin Ye . Electrochemical Transformation of Organosulfur Compounds. University Chemistry, 2025, 40(5): 311-317. doi: 10.12461/PKU.DXHX202407035
16. [16]
  Nan Xiao , Fang Sun . 二芳基硫醚化合物的构建及应用. University Chemistry, 2025, 40(6): 360-363. doi: 10.12461/PKU.DXHX202407099
17. [17]
  Hongxia Yan , Rui Wu , Weixu Feng , Yan Zhao , Yi Yan . Innovation Inspired by Classical Chemistry: Luminescent Hyperbranched Polysiloxanes. University Chemistry, 2025, 40(4): 154-159. doi: 10.12461/PKU.DXHX202409010
18. [18]
  Geyang Song , Dong Xue , Gang Li . Recent Advances in Transition Metal-Catalyzed Synthesis of Anilines from Aryl Halides. University Chemistry, 2024, 39(2): 321-329. doi: 10.3866/PKU.DXHX202308030
19. [19]
  Jiaming Xu , Yu Xiang , Weisheng Lin , Zhiwei Miao . Research Progress in the Synthesis of Cyclic Organic Compounds Using Bimetallic Relay Catalytic Strategies. University Chemistry, 2024, 39(3): 239-257. doi: 10.3866/PKU.DXHX202309093
20. [20]
  Aidang Lu , Yunting Liu , Yanjun Jiang . Comprehensive Organic Chemistry Experiment: Synthesis and Characterization of Triazolopyrimidine Compounds. University Chemistry, 2024, 39(8): 241-246. doi: 10.3866/PKU.DXHX202401029

Get Citation

PDF

XML

Metrics

PDF Downloads(0)
Abstract views(2195)
HTML views(390)

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