Research Progress of Organophosphine-Catalyzed Annulation Reaction of Electron-Deficient Alkynoates or Ynones
- Corresponding author: Abudukeremu Munira, Miao Zhiwei, miaozhiwei@nankai.edu.cn
Citation:
Zhang Jiayong, Abudukeremu Munira, Miao Zhiwei. Research Progress of Organophosphine-Catalyzed Annulation Reaction of Electron-Deficient Alkynoates or Ynones[J]. Chinese Journal of Organic Chemistry,
;2017, 37(11): 2859-2872.
doi:
10.6023/cjoc201705011
For selected reviews on tertiary organophosphine-catalyzed annulation reactions of electron-deficient alkynoates or ynones, see:
(a) Cowen, B. J.; Miller, S. J. Chem. Soc. Rev. 2009, 38, 3102.
(b) Ye, L. W.; Zhou, J.; Tang, Y. Chem. Soc. Rev. 2008, 37, 1140.
(c) Nair, V.; Menon, R. S.; Sreekanth, A. R.; Abhilash, N.; Biju, A. T. Acc. Chem. Res. 2006, 39, 520.
(d) Methot, J. L.; Roush, W. R. Adv. Synth. Catal. 2004, 346, 1035.
(e) Marinetti, A; Voituriez, A. Synlett 2010, 174.
(f) Fan, Y. C.; Kwon, O. Chem. Commun. 2013, 49, 11588.
(g) Wang, Z. M.; Xu, X. Z.; Kwon, O. Chem. Soc. Rev. 2014, 43, 2927.
(h) Xiao, Y.; Guo, H.; Kwon, O. Aldrichim. Acta 2016, 49, 3.
(a) Du, Y. S.; Yu, Y. H.; Lu, X. Y. J. Org. Chem. 2002, 67, 8901.
(b) Zhao, G. L.; Shi, M. J. Org. Chem. 2005, 70, 9975.
(c) Sampath, M.; Loh, T. P. Chem. Sci. 2010, 1, 739.
(d) Mbofana, C. T.; Miller, S. J. ACS Catal. 2014, 4, 3671.
(e) Lian, Z.; Shi, M. Eur. J. Org. Chem. 2012, 581.
(f) Kuroda, H.; Tomita, L.; Endo, T. Org. Lett. 2003, 5, 129.
(g) Ramachary, D. B.; Venkaiah, C.; Madhavachary, R. Org. Lett. 2013, 15, 3042.
(h) Wei, Y.; Shi, M. Chem.-Asian J. 2014, 9, 2720.
(i) Wang, S. X.; Han, X. Y.; Zhong, F. R.; Wang, Y. Q.; Lu, Y. X. Synlett 2011, 19, 2766.
(j) Zhao, Q. Y.; Lian, Z.; Wei, Y.; Shi, M. Chem. Commun. 2012, 48, 1724.
(k) Wang, Z. M.; Xu, X. Z.; Kwon, O. Chem. Soc. Rev. 2014, 43, 2927.
(l) Xie, P. Z.; Huang, Y. Org. Biomol. Chem. 2015, 13, 8578.
(m) Li, W. B.; Zhang, J. L. Chem. Soc. Rev. 2016, 45, 1657.
(n) Wang, T. L.; Han, X. Y.; Zhong, F. R.; Yao, W. J.; Lu, Y. X. Acc. Chem. Res. 2016, 49, 1369.
(o) Xiao, Y. M.; Sun, Z. H.; Guo, H. C.; Kwon, O. Beilstein J. Org. Chem. 2014, 10, 2089.
Zhang, C. M.; Lu, X. Y. J. Org. Chem. 1995, 60, 2906.
doi: 10.1021/jo00114a048
Xu, Z. R.; Lu, X. Y. Tetrahedron lett. 1999, 40, 549.
doi: 10.1016/S0040-4039(98)02405-8
Du, Y. S.; Lu, X. Y. J. Org. Chem. 2003, 68, 6463.
doi: 10.1021/jo034281f
Pham, T. Q.; Pyne, S. G.; Skelton, B. W.; White, A. H. J. Org. Chem. 2005, 70, 6369.
doi: 10.1021/jo050827h
Zhang, X. C.; Cao, S. H.; Wei, Y.; Shi, M. Org. Lett. 2011, 13, 1142.
doi: 10.1021/ol1031798
Sampath, M. S.; Loh, T. P. Chem. Sci. 2010, 1, 739.
doi: 10.1039/c0sc00123f
Pinto, N.; Neel, M.; Panossian, A.; Retailleau, P.; Frison, G.; Voituriez, A.; Marinetti, A. Chem.-Eur. J. 2010, 16, 1033.
doi: 10.1002/chem.200901893
Wang, J. C.; Krische, M. J. Angew. Chem., Int. Ed. 2003, 42, 5855.
doi: 10.1002/(ISSN)1521-3773
Mbofana, C. T.; Miller, S. J. ACS Catal. 2014, 4, 3671.
doi: 10.1021/cs501117h
Zhang, X. Y.; Shen, Z.; Hu, L. L.; Wang, L. J.; Lin, Y. S.; Xie, J. W.; Cui, H. L. Tetrahedron Lett. 2016, 57, 3790.
doi: 10.1016/j.tetlet.2016.07.035
Zhang, J. Y.; Zhang, M. X.; Li, Y. M.; Liu, S., Miao, Z. W. RSC Adv. 2016, 6, 107984.
doi: 10.1039/C6RA23399F
Nozaki, K.; Sato, N.; Ikeda, K.; Takaya, H. J. Org. Chem. 1996, 61, 4516.
doi: 10.1021/jo951828k
Sampath, M.; Lee, P. Y. B.; Loh. T. P. Chem. Sci. 2011, 2, 1988.
doi: 10.1039/c1sc00311a
Du, D.; Jiang, Y.; Xu, Q.; Shi, M. Adv. Synth. Catal. 2013, 355, 2249.
doi: 10.1002/adsc.201300460
Huang, Z. S.; Chen, Q. Q.; Yang, X. Q.; Liu, Y.; Zhang, L.; Liu, T.; Zhou, Q. F. Org. Chem. Front. 2017, 4, 967.
doi: 10.1039/C6QO00775A
Li, J. H.; Du, D. M. Adv. Synth. Catal. 2015, 357, 3986.
doi: 10.1002/adsc.201500675
Khong, S.; Kwon, O. J. Org. Chem. 2012, 77, 8257.
doi: 10.1021/jo3015825
Liou, K. F.; Cheng. C. H. J. Chem. Soc., Chem. Commun., 1995, 2473.
Wilson, J. E.; Sun, J.; Fu, G. C. Angew. Chem., Int. Ed. 2010, 49, 161.
doi: 10.1002/anie.200905125
Pinto, N.; Neel, M.; Panossian, A.; Retailleau, P.; Frison, G.; Voituriez, A.; Marinetti. A. Chem.-Eur. J. 2010, 16, 1033.
doi: 10.1002/chem.200901893
Ramachary, D. B.; Venkaiah, C.; Krishna, P. M. Org. Lett. 2013, 15, 4714.
doi: 10.1021/ol4020305
Liang, L.; Li, E. Q.; Xie, P. Z.; Huang, Y. Chem.-Asian J. 2014, 9, 1270.
doi: 10.1002/asia.v9.5
Kuroda, H.; Tomita, I.; Endo, T. Org. Lett. 2003, 5, 129.
doi: 10.1021/ol020198n
Yang, L. H.; Xie, P. Z.; Li, E. Q.; Li, X.; Huang, Y.; Chen, R. Y. Org. Biomol. Chem. 2012, 10, 7628.
doi: 10.1039/c2ob26338f
Chen, Q. Q.; Li, K. X.; Lu, T.; Zhou, Q. F. RSC Adv. 2016, 6, 24792.
doi: 10.1039/C6RA00580B
Ramachray, D. B.; Krishna, P. M.; Reddy, T. P. Org. Biomol. Chem. 2016, 14, 6413.
doi: 10.1039/C6OB01096B
Lian, Z.; Wei, Y.; Shi, M. Tetrahedron 2012, 68, 2401.
doi: 10.1016/j.tet.2012.01.036
Lian, Z.; Shi. M. Eur. J. Org. Chem. 2012, 581.
Lian, Z.; Shi, M. Org. Biomol. Chem., 2012, 10, 8048.
doi: 10.1039/c2ob25801c
Lian, Z.; Xu, Q.; Shi, M. Adv. Synth. Catal. 2013, 355, 3344.
doi: 10.1002/adsc.201300583
Li, Z.; Yu, H.; Liu, Y.; Zhou, L. J.; Sun, Z. H.; Guo, H. C. Adv. Synth. Catal. 2016, 358, 1880.
doi: 10.1002/adsc.v358.12
Zhu, C. Z.; Sun, Y. L.; Wei, Y.; Shi, Min. Adv. Synth. Catal. 2017, 359, 1263.
doi: 10.1002/adsc.v359.8
Zhanhui Yang , Jiaxi Xu . (m+n+…) or [m+n+…]cycloaddition?. University Chemistry, 2025, 40(3): 387-389. doi: 10.12461/PKU.DXHX202406032
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
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
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
Jiajie Li , Xiaocong Ma , Jufang Zheng , Qiang Wan , Xiaoshun Zhou , Yahao Wang . Recent Advances in In-Situ Raman Spectroscopy for Investigating Electrocatalytic Organic Reaction Mechanisms. University Chemistry, 2025, 40(4): 261-276. doi: 10.12461/PKU.DXHX202406117
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
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-. doi: 10.3866/PKU.WHXB202312010
Yan Qi , Yueqin Yu , Weisi Guo , Yongjun Liu . 过渡金属参与的有机反应案例教学与实践探索. University Chemistry, 2025, 40(6): 111-117. doi: 10.12461/PKU.DXHX202411021
Ruolin CHENG , Haoran WANG , Jing REN , Yingying MA , Huagen LIANG . Efficient photocatalytic CO2 cycloaddition over W18O49/NH2-UiO-66 composite catalyst. Chinese Journal of Inorganic Chemistry, 2024, 40(3): 523-532. doi: 10.11862/CJIC.20230349
Aiyi Xin , Jiawei Li , Xinyang Ran , Chuanjiang Fu , Zhiguo Wang . Collaborative Science and Education Based Experimental Design in Organic Chemistry: A Case Study of the Nucleophilic Substitution Reaction of 2-Hydroxymethyl-4,6-Di-Tert-Butylphenol. University Chemistry, 2025, 40(5): 366-375. doi: 10.12461/PKU.DXHX202407031
Fugui XI , Du LI , Zhourui YAN , Hui WANG , Junyu XIANG , Zhiyun DONG . Functionalized zirconium metal-organic frameworks for the removal of tetracycline from water. Chinese Journal of Inorganic Chemistry, 2025, 41(4): 683-694. doi: 10.11862/CJIC.20240291
Jiaojiao Yu , Bo Sun , Na Li , Cong Wen , Wei Li . Improvement of Classical Organic Experiment Based on the “Reverse-Step Optimization Method”: Taking Synthesis of Ethyl Acetate as an Example. University Chemistry, 2025, 40(3): 333-341. doi: 10.12461/PKU.DXHX202405177
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 CuOx/TiO2 Catalyst. Acta Physico-Chimica Sinica, 2025, 41(4): 100038-. doi: 10.3866/PKU.WHXB202408015
Xuejie Wang , Guoqing Cui , Congkai Wang , Yang Yang , Guiyuan Jiang , Chunming Xu . 碳基催化剂催化有机液体氢载体脱氢研究进展. Acta Physico-Chimica Sinica, 2025, 41(5): 100044-. doi: 10.1016/j.actphy.2024.100044
Shengbiao Zheng , Liang Li , Nini Zhang , Ruimin Bao , Ruizhang Hu , Jing Tang . Metal-Organic Framework-Derived Materials Modified Electrode for Electrochemical Sensing of Tert-Butylhydroquinone: A Recommended Comprehensive Chemistry Experiment for Translating Research Results. University Chemistry, 2024, 39(7): 345-353. doi: 10.3866/PKU.DXHX202310096
Wenxiu Yang , Jinfeng Zhang , Quanlong Xu , Yun Yang , Lijie Zhang . Bimetallic AuCu Alloy Decorated Covalent Organic Frameworks for Efficient Photocatalytic Hydrogen Production. Acta Physico-Chimica Sinica, 2024, 40(10): 2312014-. doi: 10.3866/PKU.WHXB202312014
Lewang Yuan , Yaoyao Peng , Zong-Jie Guan , Yu Fang . 二维共价有机框架作为光催化剂在有机合成中的研究进展. Acta Physico-Chimica Sinica, 2025, 41(8): 100086-. doi: 10.1016/j.actphy.2025.100086
Xinyu Yin , Haiyang Shi , Yu Wang , Xuefei Wang , Ping Wang , Huogen Yu . Spontaneously Improved Adsorption of H2O and Its Intermediates on Electron-Deficient Mn(3+δ)+ for Efficient Photocatalytic H2O2 Production. Acta Physico-Chimica Sinica, 2024, 40(10): 2312007-. doi: 10.3866/PKU.WHXB202312007
.
CCS Chemistry 综述推荐│绿色氧化新思路:光/电催化助力有机物高效升级
. CCS Chemistry, 2025, 7(10.31635/ccschem.024.202405369): -.