Decarboxylative Oxyphosphorylation of Alkynyl Carboxylic Acids with H-Phosphonates Catalyzed by Cu-Cu2O/GO-NH2

doi:10.6023/cjoc201907010

Chinese Journal of Organic Chemistry ›› 2019, Vol. 39 ›› Issue (12): 3467-3474.DOI: 10.6023/cjoc201907010 Previous Articles Next Articles

Cu-Cu₂O/GO-NH₂催化的芳基丙炔酸脱羧氧膦酰化反应研究

钟文武^a,b,c, 唐倩^a,b,c, 杨宗发^a,b, 曾雪^a,b, 甘淋玲^a,b, 兰作平^a,b, 杨元娟^a,b,c

a 重庆医药高等专科学校重庆 401331;
b 重庆市药物制剂工程技术研究中心重庆 401331;
c 国家中医药质量检测二级科研实验室重庆 401331

收稿日期:2019-07-04 修回日期:2019-08-13 发布日期:2019-08-30
通讯作者: 兰作平, 杨元娟 E-mail:lanzuop@126.com;Yang_1889@sina.com
基金资助:
Project supported by the Scientific Research Project of Chongqing Medical and Pharmaceutical College (Nos. ygz2018303, ygz2018102), the Medical Scientific Research Project of Chongqing Municipal Health and Family Planning Commission (Nos. 2012-1-093, 20142116), the Chinese Medicine Science and Technology Project of Chongqing Municipal Health and Family Planning Commission (No. ZY201402158), and the Scientific and Technological Research Project of Chongqing Municipal Education Commission (No. KJ1726394).

Decarboxylative Oxyphosphorylation of Alkynyl Carboxylic Acids with H-Phosphonates Catalyzed by Cu-Cu₂O/GO-NH₂

Zhong Wenwu^a,b,c, Tang Qian^a,b,c, Yang Zongfa^a,b, Zeng Xue^a,b, Gan Linling^a,b, Lan Zuoping^a,b, Yang Yuanjuan^a,b,c

a Chongqing Medical and Pharmaceutical College, Chongqing 401331;
b Chongqing Engineering Technology Research Center of Pharmaceutical Sciences, Chongqing 401331;
c National Second-level Scientific Research Laboratory of the Quality Testing of Traditional Chinese Medicine, Chongqing 401331

Received:2019-07-04 Revised:2019-08-13 Published:2019-08-30
Supported by:
Project supported by the Scientific Research Project of Chongqing Medical and Pharmaceutical College (Nos. ygz2018303, ygz2018102), the Medical Scientific Research Project of Chongqing Municipal Health and Family Planning Commission (Nos. 2012-1-093, 20142116), the Chinese Medicine Science and Technology Project of Chongqing Municipal Health and Family Planning Commission (No. ZY201402158), and the Scientific and Technological Research Project of Chongqing Municipal Education Commission (No. KJ1726394).

1. .pdf(2444KB)

Abstract

A graphene based hybrid with copper nanoparticles (Cu-Cu₂O/GO-NH₂) as a heterogeneous catalyst for the preparation of β-ketophosphonates was investigated. Compared with traditional homogeneous catalysis, Cu-Cu₂O/GO-NH₂ catalyst can be recovered from the reaction system. The present methodology provides a facile and efficient approach to access a wide range of β-ketophosphonates in good yields. This reaction can be conducted under base-free conditions without any external co-catalysts, which provides an alternative strategy for the synthesis of β-ketophosphonates.

Key words: Cu nanoparticles, graphene, oxyphosphorylation, heterogeneous catalysis, β-ketophosphonates

Cite this article

Zhong Wenwu, Tang Qian, Yang Zongfa, Zeng Xue, Gan Linling, Lan Zuoping, Yang Yuanjuan. Decarboxylative Oxyphosphorylation of Alkynyl Carboxylic Acids with H-Phosphonates Catalyzed by Cu-Cu₂O/GO-NH₂[J]. Chinese Journal of Organic Chemistry, 2019, 39(12): 3467-3474.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

share this article

References

[1] (a) Balg, C.; Blais, S. P.; Bernier, S. J.; Huot, L.; Couture, M.; Lapointe, J.; Chenevert, R. Bioorg. Med. Chem. 2007, 15, 295.
(b) Auberger, N.; Gravier-Pelletier, C.; Le Merrer, Y. Eur. J. Org. Chem. 2009, 3323.
(c) Yang, G.-C.; Shen, C.-R.; Zhang, L.; Zhang, W.-B. Tetrahedron Lett. 2011, 52, 5032.
(d) Hu, G.-B.; Zhang, Y.; Su, J.; Li, Z.-Z.; Gao, Y.-X.; Zhao, Y.-F. Org. Biomol. Chem. 2015, 13, 8221.
(e) Yang, Y.; Cai, T.; Wen, T.-B. Chin. J. Org. Chem. 2017, 37, 176(in Chinese). (杨玉, 蔡涛, 温庭斌, 有机化学, 2017, 37, 176.)
[2] (a) Szewczyk, M. Z.; Rapp, M.; Virieux, D.; Pirat, J.-L.; Koroniak, H. New J. Chem., 2017, 41, 6322.
(b) Radwan-Olszewska, K.; Palacios, F.; Kafarski, P. J. Org. Chem. 2011, 76, 1170.
(c) Wang, H.-B.; Fu, Q.; Zhang, Z.-J.; Gao, M.; Ji, J.-X.; Yi, D. Chin. J. Org. Chem. 2018, 38, 134(in Chinese). (王华斌, 付强, 张智杰, 高明, 姬建新, 易东, 有机化学, 2018, 38, 134.)
(d) Chen, X.; Hou, C.; Li, Q.; Liu, Y.; Yang, R.; Hu, X. Chin. J. Catal. 2016, 37, 1389.
[3] (a) Xie, L.-Y.; Yuan, R.; Wang, R.-J.; Peng, Z.-H.; Xiang, J.-N.; He, W.-M. Eur. J. Org. Chem. 2014, 2668.
(b) Wei, W.; Ji, J. X. Angew. Chem. Int. Ed. Engl. 2011, 50, 9097.
(c) Ke, J.; Tang, Y.-L.; Yi, H.; Li, Y.-L.; Cheng, Y.-D.; Liu, C.; Lei, A.-W. Angew. Chem. Int. Ed. Engl. 2015, 54, 6604.
(d) Gu, J.; Cai, C. Org. Biomol. Chem. 2017, 15, 4226.
(e) Zhang, P.-B.; Zhang, L.-L.; Gao, Y.-Z.; Xu, J.; Fang, H.; Tang, G.; Zhao, Y.-F. Chem. Commun. 2015, 51, 7839.
(f) Liu, K.; Liu, H.; Wang, W.; Ou, L.; Wang, J.; Hu, B. Chin. J. Org. Chem. 2014, 34, 2007(in Chinese). (刘开建, 刘宏伟, 王文革, 欧丽娟, 王津津, 胡波年, 有机化学, 2014, 34, 2007.)
[4] (a) Li, L.-L.; Huang, W.-B.; Chen, L.-J.; Dong, J.-X.; Ma, X.-B.; Peng, Y.-G. Angew. Chem. Int. Ed. 2017, 56, 10539.
(b) Liang, W.; Zhang, Z.-J.; Yi, D.; Fu, Q.; Chen, S.-Y.; Yang, L.; Du, F.-T.; Ji, J.-X.; Wei, W. Chin. J. Chem. 2017, 35, 1378.
(c) Tang, P.; Zhang, C.; Chen, E.; Chen, B.-H.; Chen, W.-T.; Yu, Y.-P. Tetrahedron Lett. 2017, 58, 2157.
(d) Zhou, P.; Hu, B.; Li, L.; Rao, K.; Yang, J.; Yu, F.-C. J. Org. Chem. 2017, 82, 13268.
(e) Zeng, Y.-F.; Tan, D.-H.; Lv, W.-X.; Li, Q.-J.; Wang, H.-G. Eur. J. Org. Chem. 2015, 2015, 4335.
(f) Zhou, M.-X.; Chen, M.; Zhou, Y.; Yang, K.; Su, J.-H.; Du, J.-F.; Song, Q.-L. Org. Lett. 2015, 17, 1786.
[5] (a) Zhong, W.-W.; Tan, T.; Shi, L.; Zeng, X. Synlett 2018, 14, 1379.
(b) Qian, H.-F.; Li, C.-K.; Zhou, Z.-H.; Tao, Z.-K.; Shoberu, A.; Zou, J.-P. Org. Lett. 2018, 20, 5947.
(c) Yuan, T.; Chen, F.; Lu, G.-P. New J. Chem. 2018, 42, 13957.
[6] Hosseinian, A.; Hosseini Nasab, F. A.; Ahmadi, S.; Rahmani, Z.; Vessally, E. RSC Adv. 2018, 8, 26383.
[7] (a) Gutierrez, V.; Mascaró, E.; Alonso, F.; Moglie, Y.; Radivoy, G. RSC Adv. 2015, 5, 65739.
(b) Fortunato, L.; Moglie, Y.; Dorn, V.; Radivoy, G. RSC Adv. 2017, 7, 18707.
[8] (a) Candu, N.; Dhakshinamoorthy, A.; Apostol, N.; Teodorescu, C.; Corma, A.; Garcia, H.; Parvulescu, V. I. J. Catal. 2017, 352, 59.
(b) Wang, F.-Y.; Yao, K.-P.; Peng, A.-S.; Wang, C.-Y. Chemistry 2017, 80, 524(in Chinese). (王方元, 姚克平, 彭安顺, 王程宇, 化学通报, 2017, 80, 524.)
(c) Basak, P.; Ghosh, P. Synth. Commun. 2018, 48, 2584.
(d) Oliveira, R. L.; Oliveira, C. S.; Landers, R.; Correia, C. R. D. ChemistrySelect 2018, 3, 535.
(e) Wang, Y.-B.; Wang, J.-R.; Wang, B.; Wang, Y.-Y.; Jin, G.-Q.; Guo, X.-G. Catal. Surv. Asia 2018, 22, 123.
(f) Sengupta, D.; Pandey, M. K.; Mondal, D.; Radhakrishna, L.; Balakrishna, M. S. Eur. J. Inorg. Chem. 2018, 2018, 3374.
[9] Dhopte, K. B.; Raut, D. S.; Patwardhan, A. V.; Nemade, P. R. Synth. Commun. 2015, 45, 778.
[10] Chen, X.; Li, X.; Chen, X.-L.; Qu, L.-B.; Chen, J. Y.; Sun, K.; Liu, Z. D.; Bi, W. Z.; Xia, Y. Y.; Wu, H. T.; Zhao, Y. F. Chem. Commun. 2015, 51, 3846.

[1]	Jiyu Liu, Shengyu Li, Kuan Chen, Yin Zhu, Yuan Zhang. Triphenylamine-Based Ordered Mesoporous Polymer as a Metal-Free Photocatalyst for Oxidation of Thiols to Disulfide [J]. Chinese Journal of Organic Chemistry, 2024, 44(2): 605-612.
[2]	Xu Liao, Zeyu Wang, Wufei Tang, Jinqing Lin. Progress in Porous Organic Polymer for Chemical Fixation of Carnbon Dioxide [J]. Chinese Journal of Organic Chemistry, 2023, 43(8): 2699-2710.
[3]	Shiguo Ou, Ruirui Chai, Jiahao Li, Dawei Wang, Xinxin Sang. Metal-Organic Framework Derived Phytate-Iron for Efficient Synthesis of 2-Arylbenzoxazole via Hydrogen Transfer Strategy [J]. Chinese Journal of Organic Chemistry, 2023, 43(8): 2934-2945.
[4]	Baichuan Mo, Chunxia Chen, Jinsong Peng. Research Progress in Application of Lignin and Its Derivatives Supported Metal Catalysts in Organic Synthesis [J]. Chinese Journal of Organic Chemistry, 2023, 43(4): 1215-1240.
[5]	Binghao Huo, Conghui Guo, Zhanhui Xu. Mn(acac)₃ Promoted Radical Oxidative Coupling Reaction of Enol Esters with Phosphites to Synthesize β-Ketophosphonates [J]. Chinese Journal of Organic Chemistry, 2023, 43(11): 3989-3996.
[6]	Rui Bai, Xujuan Liu, Wenyu Luo, Shanshan Liu, Linyu Jiao. Research Progress of Chan-Lam Coupling Reaction in Heterogeneous Catalysis [J]. Chinese Journal of Organic Chemistry, 2022, 42(8): 2342-2354.
[7]	JIan Xiao, Zhiying Wu, Ziyi Chen, Pengfei Zhao. Tetraethylenepentamine Functionalized Phenolic Resin as Highly Active Acid-Base Bifunctional Catalyst for Knoevenagel Condensation Reaction [J]. Chinese Journal of Organic Chemistry, 2022, 42(4): 1179-1187.
[8]	Qiang Huang, Tingting Deng, Jiayun Zhu, Jun Li, Feifei Li. Study on the Green Synthesis of β-Hydroxy-1,2,3-triazoles Catalyzed by An Amino-Functionalized Graphene-Supported Ag-Cu Composites [J]. Chinese Journal of Organic Chemistry, 2022, 42(2): 534-542.
[9]	Yaoyao Zhang, Lijie Zhou, Biao Han, Weishuang Li, Bojie Li, Lei Zhu. Research Progress of Chitosan Supported Copper Catalyst in Organic Reactions [J]. Chinese Journal of Organic Chemistry, 2022, 42(1): 33-53.
[10]	Xin Chen, Chunxia Chen, Jinsong Peng. Research Progress of Cellulose and Its Derivatives Supported Copper Catalyst Catalyzed Organic Reactions [J]. Chinese Journal of Organic Chemistry, 2021, 41(4): 1319-1336.
[11]	Yuxuan Chen, Qi Chen, Zhanhui Zhang. Application of Covalent Organic Framework Materials as Heterogeneous Ligands in Organic Synthesis [J]. Chinese Journal of Organic Chemistry, 2021, 41(10): 3826-3843.
[12]	Feiyu Wang, Zhipeng Zhang, Fei Huang. Research Progress of O—H Insertion Reaction Based on Diazo Ester [J]. Chinese Journal of Organic Chemistry, 2021, 41(1): 144-157.
[13]	Xu Zi-Yue, Luo Yi, Wang Hui, Zhang Dan-Wei, Li Zhan-Ting. Porous Organic Polymers as Heterogeneous Catalysts for Visible Light-Induced Organic Transformations [J]. Chinese Journal of Organic Chemistry, 2020, 40(11): 3777-3793.
[14]	Hao Bingjie, Song Tao, Huang Xiaoyu, Ye Mao, Qian Wenhao. Organic Reactions in Covalent Functionalization of Graphene [J]. Chinese Journal of Organic Chemistry, 2020, 40(10): 3279-3288.
[15]	Ng Chun-Fai, Wong Wai-Shing, Ip Ho-Wang, Lau Wing-Wa, Sun Xiao-Qing, Tse Ho-Wing, He Lisi, Cheung Enoch, Kuck Dietmar, Chow Hak-Fun. Nonplanar Nanographenes Based on Tribenzotriquinacene or Fenestrindane Core [J]. Chinese Journal of Organic Chemistry, 2020, 40(10): 3017-3025.

Cu-Cu₂O/GO-NH₂催化的芳基丙炔酸脱羧氧膦酰化反应研究

Decarboxylative Oxyphosphorylation of Alkynyl Carboxylic Acids with H-Phosphonates Catalyzed by Cu-Cu₂O/GO-NH₂

PDF

Supporting Info.

Knowledge

Abstract

Cite this article

share this article

References

Related Articles 15

Recommended Articles

Metrics

Comments

Cu-Cu2O/GO-NH2催化的芳基丙炔酸脱羧氧膦酰化反应研究