Recent Progress on Cu-Catalyzed Conjugate Silylation to Unsaturated Compounds
- Corresponding author: Chen Yali, ylchen@staff.shu.edu.cn Tian Ping, tianping@sioc.ac.cn
	            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
						
					
				
					 
				
	        
 
	                
				 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.
				 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.
				Ilardi, E. A.; Stivala, C. E.; Zakarian, A. Org. Lett. 2008, 10, 1727.
												 doi: 10.1021/ol800341z
											
										
				 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.)
Qiu, H.-Y.; Lai, G.-Q. Chin. J. Org. Chem. 2007, 27, 806(in Chinese).
				Hengge E.; Holtschmidt, N. J. Organomet. Chem. 1968, 12, 5.
												 doi: 10.1016/S0022-328X(00)90890-8
											
										
				Still, W. C. J. Org. Chem. 1976, 41, 3063.
												 doi: 10.1021/jo00880a044
											
										
				 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.
Fleming, I.; Newton, T. W. J. Chem. Soc., Perkin Trans. 11984, 1805.
				 Sharma, S.; Oehlschlager, A. C. Tetrahedron 1989, 45, 557; 
(b) Koreeda, M.; Koo, S. Tetrahedron Lett. 1990, 31, 831.
				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.
				Lipshutz, B. H.; Sclafani, J. A.; Takanami, T. J. Am. Chem. Soc. 1998, 120, 4021.
												 doi: 10.1021/ja980152i
											
										
				Ito, H.; Ishizuka, T.; Tateiwa, J.; Sonoda, M.; Hosomi, A. J. Am. Chem. Soc. 1998, 120, 11196.
												 doi: 10.1021/ja9822557
											
										
				 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.
				 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.
				Clark, C. T.; Lake, J. F.; Scheidt, K. A. J. Am. Chem. Soc. 2004, 126, 84.
												 doi: 10.1021/ja038530t
											
										
				Lee, K.; Hoveyda, A. H. J. Am. Chem. Soc. 2010, 132, 2898
												 doi: 10.1021/ja910989n
											
										
				 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.
				Welle, A.; Petrignet, J.; Tinant, B.; Wouters, J.; Riant, O. Chem. Eur. J. 2010, 16, 10980.
												 doi: 10.1002/chem.v16:36
											
										
				Ibrahem, I.; Santoro, S.; Himo, F.; Córdova, A. Adv. Synth. Catal. 2011, 353, 245.
												 doi: 10.1002/adsc.201000908
											
										
				Calderone, J. A.; Santos, W. L. Org. Lett. 2012, 14, 2090.
												 doi: 10.1021/ol300618j
											
										
				Iannazzo, L.; Molander, G. A. Eur. J. Org. Chem. 2012, 16, 4923.
										
				Pace, V.; Rae, J. P.; Harb, H. Y.; Procter, D. J. Chem. Commun. 2013, 49, 5150.
												 doi: 10.1039/c3cc42160k
											
										
				Pace, V.; Rae, J. P.; Procter, D. J. Org. Lett. 2014, 16, 476.
												 doi: 10.1021/ol4033623
											
										
				Plotzitzka, J.; Kleeberg, C. Organometallics 2014, 33, 6915.
												 doi: 10.1021/om500989w
											
										
				Calderone, J. A.; Santos, W. L. Angew. Chem., Int. Ed. 2014, 53, 4154.
												 doi: 10.1002/anie.201310695
											
										
				Kitanosono, T.; Zhu, L.; Liu, C.; Xu, P.; Kobayashi, S. J. Am. Chem. Soc. 2015, 137, 15422.
												 doi: 10.1021/jacs.5b11418
											
										
				Lee, K.; Wu, H.; Haeffner, F.; Hoveyda, A. H. Organometallics 2012, 31, 7823.
												 doi: 10.1021/om300790t
											
										
				López, A.; Parra, A.; Carlos, J.-B. Tortosa, M. Chem. Commun. 2015, 51, 17684.
												 doi: 10.1039/C5CC06653K
											
										
				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
											
										
 
						
						
						
	                Xudong Lv , Tao Shao , Junyan Liu , Meng Ye , Shengwei Liu . Paired Electrochemical CO2 Reduction and HCHO Oxidation for the Cost-Effective Production of Value-Added Chemicals. Acta Physico-Chimica Sinica, 2024, 40(5): 2305028-0. doi: 10.3866/PKU.WHXB202305028
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
Qianwen Han , Tenglong Zhu , Qiuqiu Lü , Mahong Yu , Qin Zhong . Performance and Electrochemical Asymmetry Optimization of Hydrogen Electrode Supported Reversible Solid Oxide Cell. Acta Physico-Chimica Sinica, 2025, 41(1): 100005-0. doi: 10.3866/PKU.WHXB202309037
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
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
Yerong Chen , Bingbin Yang , Xinglei He , Yuqi Lin , Keyin Ye . Enzyme-Directed Evolution Enables Bioconversion of Organosilicon Compounds. University Chemistry, 2025, 40(10): 121-129. doi: 10.12461/PKU.DXHX202411054
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
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
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
Hanxue LIU , Shijie LI , Meng REN , Xuling XUE , Hongke LIU . Design and antitumor properties of dehydroabietic acid functionalized cyclometalated iridium(Ⅲ) complex. Chinese Journal of Inorganic Chemistry, 2025, 41(8): 1483-1494. doi: 10.11862/CJIC.20250031
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
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
Hao Wu , Zhen Liu , Dachang Bai . 1H NMR Spectrum of Amide Compounds. University Chemistry, 2024, 39(3): 231-238. doi: 10.3866/PKU.DXHX202309020
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
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
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
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
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
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
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