Oxidative C—H Alkynylation of Unactivated Acyclic Ethers
- Corresponding author: Liu Lei, leiliu@sdu.edu.cn
Citation:
Guan Honghao, Chen Lei, Liu Lei. Oxidative C—H Alkynylation of Unactivated Acyclic Ethers[J]. Acta Chimica Sinica,
;2018, 76(6): 440-444.
doi:
10.6023/A18030083
(a) Godula, K. ; Sames, D. Science 2006, 312, 67; (b) Davies, H. M. L. Angew. Chem., Int. Ed. 2006, 45, 6422; (c) Gutekunst, W. R. ; Baran, P. S. Chem. Soc. Rev. 2011, 40, 1976; (d) Giri, R. ; Shi, B. F. ; Engle, K. M. ; Maugel, N. ; Yu, J. Q. Chem. Soc. Rev. 2009, 38, 3242.
(a) Wender, P. A. ; Verma, V. A. ; Paxton, T. J. ; Pillow, T. H. Acc. Chem. Res. 2008, 41, 40; (b) Trost, B. M. Acc. Chem. Res. 2002, 35, 695.
For cross-dehydrogenative coupling of amines, see: (a) Li, Z. ; Li, C. J. J. Am. Chem. Soc. 2004, 126, 11810; (b) Li, Z. ; Li, C. J. J. Am. Chem. Soc. 2005, 127, 3672; (c) Li, Z. ; Li, C. J. J. Am. Chem. Soc. 2005, 127, 6968; (d) Li, Z. ; Yu, R. ; Li, H. Angew. Chem., Int. Ed. 2008, 47, 7497; (e) Murahashi, S. I. ; Nakae, T. ; Terai, H. ; Komiya, N. J. Am. Chem. Soc. 2008, 130, 11005; (f) Yang, F. ; Li, J. ; Xie, J. ; Huang, Z. -Z. Org. Lett. 2010, 12, 5214; (g) Hari, D. P. ; König, B. Org. Lett. 2011, 13, 3852; (h) Boess, E. ; Sureshkumar, D. ; Sud, A. ; Wirtz, C. ; Farès, C. ; Klussmann, M. J. Am. Chem. Soc. 2011, 133, 8106; (i) Richter, H. ; García Mancheño, O. Eur. J. Org. Chem. 2010, 4460; (j) Meng, Q. -Y. ; Zhong, J. -J. ; Liu, Q. ; Gao, X. -W. ; Zhang, H. -H. ; Lei, T. ; Li, Z. -J. ; Feng, K. ; Chen, B. ; Tung, C. -H. ; Wu, L. -Z. J. Am. Chem. Soc. 2013, 135, 19052; (k) Liu, X. ; Sun, B. ; Xie, Z. ; Qin, X. ; Liu, L. ; Lou, H. J. Org. Chem. 2013, 78, 3104; (l) Xie, Z. ; Liu, L. ; Chen, W. ; Zheng, H. ; Xu, Q. ; Yuan, H. ; Lou, H. Angew. Chem., Int. Ed. 2014, 53, 3904; (m) Wu, C. -J. ; Zhong, J. -J. ; Meng, Q. -Y. ; Lei, T. ; Gao, X. -W. ; Tung, C. -H. ; Wu, L. -Z. Org. Lett. 2015, 17, 884; (n) Long, H. ; Wang, G. ; Lu, R. ; Xu, M. ; Zhang, K. ; Qi, S. ; He, Y. ; Bu, Y. ; Liu, L. Org. Lett. 2017, 19, 2146.
For asymmetric cross-dehydrogenative coupling of amines, see: (a) Zhang, J. ; Tiwari, B. ; Xing, C. ; Chen, X. ; Chi, Y. R. Angew. Chem., Int. Ed. 2012, 51, 3649; (b) Zhang, G. ; Zhang, Y. ; Wang, R. ; Angew. Chem., Int. Ed. 2011, 50, 10429; (c) Zhang, G. ; Ma, Y. ; Wang, S. ; Kong, W. ; Wang, R. Chem. Sci. 2013, 4, 2645; (d) Neel, A. J. ; Hehn, J. P. ; Tripet, P. F. ; Toste, F. D. J. Am. Chem. Soc. 2013, 135, 14044; (e) Liu, X. ; Sun, S. ; Meng, Z. ; Lou, H. ; Liu, L. Org. Lett. 2015, 17, 2396; (f) Xie, Z. ; Liu, X. ; Liu, L. Org. Lett. 2016, 18, 2982; (g) Xie, Z. ; Zan, X. ; Sun, S. ; Pan, X. ; Liu, L. Org. Lett. 2016, 18, 3944; (h) Yang, Q. ; Zhang, L. ; Ye, C. ; Luo, S. ; Wu, L. -Z. ; Tung, C. -H. Angew. Chem., Int. Ed. 2017, 56, 3694; (i) Fu, N. ; Li, L. ; Yang, Q. ; Luo, S. Org. Lett. 2017, 19, 2122.
For cross-dehydrogenative coupling of cyclic benzylic ethers, see: (a) Zhang, Y. H. ; Li, C. J. J. Am. Chem. Soc. 2006, 128, 4242; (b) Zhang, Y. H. ; Li, C. J. Angew. Chem., Int. Ed. 2006, 45, 1949; (c) Ghobrial, M. ; Harhammer, K. ; Mihovilovic, M. D. ; Schnürch, M. Chem. Commun. 2010, 46, 8836; (d) Correia, C. A. ; Li, C. J. Heterocycles 2010, 82, 555; (e) Richter, H. ; Rohlmann, R. ; García Mancheño, O. Chem. Eur. J. 2011, 17, 11622; (f) Xiang, S. -K. ; Zhang, B. ; Zhang, L. -H. ; Cui, Y. ; Jiao, N. Sci. China Chem. 2012, 55, 50; (g) Park, S. J. ; Price, J. R. ; Todd, M. H. J. Org. Chem. 2012, 77, 949; (h) Liu, X. ; Sun, B. ; Xie, Z. ; Qin, X. ; Liu, L. ; Lou, H. J. Org. Chem. 2013, 78, 3104; (i) Chen, W. ; Xie, Z. ; Zheng, H. ; Lou, H. ; Liu, L. Org. Lett. 2014, 16, 5988.
Asymmetric cross-dehydrogenative coupling of cyclic benzylic ethers, see: Meng, Z. ; Sun, S. ; Yuan, H. ; Lou, H. ; Liu, L. Angew. Chem., Int. Ed. 2014, 53, 543.
For cross-dehydrogenative coupling of unactivated cyclic ethers, see: (a) Wu, Z. ; Pi, C. ; Cui, X. ; Bai, J. ; Wu, Y. Adv. Synth. Catal. 2013, 355, 1971; (b) Huang, X. -F. ; Zhu, Z. -Q. ; Huang, Z. -Z. Tetrahedron 2013, 69, 8579; (c) Liu, D. ; Liu, C. ; Li, H. ; Lei, A. Chem. Commun. 2014, 50, 3623; (d) Wei, W. -T. ; Song, R. -J. ; Li, J. -H. Adv. Synth. Catal. 2014, 356, 1703; (e) Jin, J. ; MacMillan, D. W. C. Angew. Chem., Int. Ed. 2015, 54, 1565; (f) Jin, L. ; Feng, J. ; Lu, G. ; Cai, C. Adv. Synth. Catal. 2015, 357, 2105; (g) Niu, B. ; Zhao, W. ; Ding, Y. ; Bian, Z. ; Pittman Jr. C. U. ; Zhou, A. ; Ge, H. J. Org. Chem. 2015, 80, 7251; (h) Li, Q. ; Hu, W. ; Hu, R. ; Lu, H. ; Li, G. Org. Lett. 2017, 19, 4676; (i) Liu, S. ; Liu, A. ; Zhang, Y. ; Wang, W. Chem. Sci. 2017, 8, 4044; (j) Liu, D. ; Liu, C. ; Lei A. Angew. Chem., Int. Ed. 2013, 52, 4453; (k) Yang, Q. ; Choy, P. Y. ; Wu, Y. ; Fan, B. ; Kwong, F. Y. Org. Biomol. Chem. 2016, 14, 2608; (l) Zhang, L. ; Yi, H. ; Wang, J. ; Lei, A. J. Org. Chem. 2017, 82, 10704; (m) Wu, J. ; Zhou, Y. ; Zhou, Y. ; Chiang, C. -W. ; Lei, A. ACS Catal. 2017, 7, 8320; (n) Xie, Z. ; Cai, Y. ; Hu, H. ; Lin, C. ; Jiang, J. ; Chen, Z. ; Wang, L. ; Pan, Y. Org. Lett. 2013, 15, 4600; (o) Zhou, L. ; Tang, S. ; Qi, X. ; Lin, C. ; Liu, K. ; Liu, C. ; Lan, Y. ; Lei, A. Org. Lett. 2014, 16, 3404; (p) Tang, S. ; Wang, P. ; Li, H. ; Lei, A. Nat. Commun. 2016, 7, 11676.
For cross-dehydrogenative coupling of acyclic benzylic ethers, see: (a) Liu, L. ; Floreancig, P. E. Org. Lett. 2009, 11, 3152; (b) Xie, Y. ; Yu, M. ; Zhang, Y. Synthesis 2011, 17, 2803.
Diederich, F. ; Stang, P. J. ; Tykwinski, R. R. Acetylene Chemistry: Chemistry, Biology and Material Science, Wiley-VCH, Weinheim, 2005.
Wan, M.; Meng, Z.; Lou, H.; Liu, L. Angew. Chem., Int. Ed. 2014, 53, 13845.
doi: 10.1002/anie.201407083
Zhang, Q.; Lv, J.; Luo, S. Acta Chim. Sinica 2016, 74, 61(in Chinese).
doi: 10.3866/PKU.WHXB201511101
Usugi, S.-i.; Yorimitsu, H.; Shinokubo, H.; Oshima, K. Bull. Chem. Soc. Jpn. 2002, 75, 2687.
doi: 10.1246/bcsj.75.2687
In-situ generated carbocation oxidation system shows better reactivity than pre-prepared one. At present, the origin of this difference in activity is still unknown.
Ping Ye , Lingshuang Qin , Mengyao He , Fangfang Wu , Zengye Chen , Mingxing Liang , Libo Deng . 荷叶衍生多孔碳的零电荷电位调节实现废水中电化学捕集镉离子. Acta Physico-Chimica Sinica, 2025, 41(3): 2311032-. doi: 10.3866/PKU.WHXB202311032
Zhuo Wang , Xue Bai , Kexin Zhang , Hongzhi Wang , Jiabao Dong , Yuan Gao , Bin Zhao . MOF模板法合成氮掺杂碳材料用于增强电化学钠离子储存和去除. Acta Physico-Chimica Sinica, 2025, 41(3): 2405002-. doi: 10.3866/PKU.WHXB202405002
Li'na ZHONG , Jingling CHEN , Qinghua ZHAO . Synthesis of multi-responsive carbon quantum dots from green carbon sources for detection of iron ions and L-ascorbic acid. Chinese Journal of Inorganic Chemistry, 2025, 41(4): 709-718. doi: 10.11862/CJIC.20240280
Yueguang Chen , Wenqiang Sun . “Carbon” Adventures. University Chemistry, 2024, 39(9): 248-253. doi: 10.3866/PKU.DXHX202308074
Wendian XIE , Yuehua LONG , Jianyang XIE , Liqun XING , Shixiong SHE , Yan YANG , Zhihao HUANG . Preparation and ion separation performance of oligoether chains enriched covalent organic framework membrane. Chinese Journal of Inorganic Chemistry, 2024, 40(8): 1528-1536. doi: 10.11862/CJIC.20240050
Lei Shu , Zimin Duan , Yushen Kang , Zijian Zhao , Hong Wang , Lihua Zhu , Hui Xiong , Nan Wang . An Exploration of the CO2-Involved Carbon Cycle World. University Chemistry, 2024, 39(5): 144-153. doi: 10.3866/PKU.DXHX202309084
Lei Shu , Zhengqing Hao , Kai Yan , Hong Wang , Lihua Zhu , Fang Chen , Nan Wang . Development of a Double-Carbon Related Experiment: Preparation, Characterization and Carbon-Capture Ability of Eggshell-Derived CaO. University Chemistry, 2024, 39(4): 149-156. doi: 10.3866/PKU.DXHX202310134
Yuyao Wang , Zhitao Cao , Zeyu Du , Xinxin Cao , Shuquan Liang . Research Progress of Iron-based Polyanionic Cathode Materials for Sodium-Ion Batteries. Acta Physico-Chimica Sinica, 2025, 41(4): 100035-. doi: 10.3866/PKU.WHXB202406014
Wenjun Zheng . Application in Inorganic Synthesis of Ionic Liquids. University Chemistry, 2024, 39(8): 163-168. doi: 10.3866/PKU.DXHX202401020
Guoze Yan , Bin Zuo , Shaoqing Liu , Tao Wang , Ruoyu Wang , Jinyang Bao , Zhongzhou Zhao , Feifei Chu , Zhengtong Li , Yusuke Yamauchi , Saad Melhi , Xingtao Xu . Opportunities and Challenges of Capacitive Deionization for Uranium Extraction from Seawater. Acta Physico-Chimica Sinica, 2025, 41(4): 100032-. doi: 10.3866/PKU.WHXB202404006
Kai CHEN , Fengshun WU , Shun XIAO , Jinbao ZHANG , Lihua ZHU . PtRu/nitrogen-doped carbon for electrocatalytic methanol oxidation and hydrogen evolution by water electrolysis. Chinese Journal of Inorganic Chemistry, 2024, 40(7): 1357-1367. doi: 10.11862/CJIC.20230350
Siyi ZHONG , Xiaowen LIN , Jiaxin LIU , Ruyi WANG , Tao LIANG , Zhengfeng DENG , Ao ZHONG , Cuiping HAN . Targeting imaging and detection of ovarian cancer cells based on fluorescent magnetic carbon dots. Chinese Journal of Inorganic Chemistry, 2024, 40(8): 1483-1490. doi: 10.11862/CJIC.20240093
Guojie Xu , Fang Yu , Yunxia Wang , Meng Sun . Introduction to Metal-Catalyzed β-Carbon Elimination Reaction of Cyclopropenones. University Chemistry, 2024, 39(8): 169-173. doi: 10.3866/PKU.DXHX202401060
Zhuo WANG , Xiaotong LI , Zhipeng HU , Junqiao PAN . Three-dimensional porous carbon decorated with nano bismuth particles: Preparation and sodium storage properties. Chinese Journal of Inorganic Chemistry, 2025, 41(2): 267-274. doi: 10.11862/CJIC.20240223
Xiangyu CAO , Jiaying ZHANG , Yun FENG , Linkun SHEN , Xiuling ZHANG , Juanzhi YAN . Synthesis and electrochemical properties of bimetallic-doped porous carbon cathode material. Chinese Journal of Inorganic Chemistry, 2025, 41(3): 509-520. doi: 10.11862/CJIC.20240270
Yongwei ZHANG , Chuang ZHU , Wenbin WU , Yongyong MA , Heng YANG . Efficient hydrogen evolution reaction activity induced by ZnSe@nitrogen doped porous carbon heterojunction. Chinese Journal of Inorganic Chemistry, 2025, 41(4): 650-660. doi: 10.11862/CJIC.20240386
Zhaomei LIU , Wenshi ZHONG , Jiaxin LI , Gengshen HU . Preparation of nitrogen-doped porous carbons with ultra-high surface areas for high-performance supercapacitors. Chinese Journal of Inorganic Chemistry, 2024, 40(4): 677-685. doi: 10.11862/CJIC.20230404
Yixuan Gao , Lingxing Zan , Wenlin Zhang , Qingbo Wei . Comprehensive Innovation Experiment: Preparation and Characterization of Carbon-based Perovskite Solar Cells. University Chemistry, 2024, 39(4): 178-183. doi: 10.3866/PKU.DXHX202311091
Yajun Jian , Quanguo Zhai , Quan Gu , Shengli Gao . Reconstruction and Practice of the Teaching Content of “Carbon Group Elements” in Inorganic Chemistry to Reflect Comprehensive Education Function. University Chemistry, 2024, 39(11): 96-107. doi: 10.12461/PKU.DXHX202403006
Hong LI , Xiaoying DING , Cihang LIU , Jinghan ZHANG , Yanying RAO . Detection of iron and copper ions based on gold nanorod etching colorimetry. Chinese Journal of Inorganic Chemistry, 2024, 40(5): 953-962. doi: 10.11862/CJIC.20230370