Cu(I)-Catalyzed Three-Component Reaction of Propargylic Alcohol, Secondary Amines and Atmospheric CO2

doi:10.6023/cjoc201512037

Chin. J. Org. Chem. ›› 2016, Vol. 36 ›› Issue (4): 744-751.DOI: 10.6023/cjoc201512037 Previous Articles Next Articles

ARTICLE

铜(I)催化的常压二氧化碳、炔丙醇和仲胺三组分反应

李雪冬, 郎咸东, 宋清文, 郭亚坤, 何良年

南开大学元素有机化学国家重点实验室天津化学化工协同创新中心天津 300071

收稿日期:2015-12-25 修回日期:2016-01-30 发布日期:2016-02-18
通讯作者: 何良年 E-mail:heln@nankai.edu.cn
基金资助:
国家自然科学基金(Nos.21472103,21121002)、教育部博士点基金(No.20130031110013)和国家基础科学人才培养基金(No.J1103306)资助项目.

Cu(I)-Catalyzed Three-Component Reaction of Propargylic Alcohol, Secondary Amines and Atmospheric CO₂

Li Xuedong, Lang Xiandong, Song Qingwen, Guo Yakun, He Liangnian

State Key Laboratory and Institute of Elemento-Organic. Chemistry, Collaborative Innovation Center of Chemical Science and Engineering, Nankai University, Tianjin 300071

Received:2015-12-25 Revised:2016-01-30 Published:2016-02-18
Supported by:
Project supported by the National Natural Sciences Foundation of China (Nos. 21472103, 21121002), the Specialized Research Fund for the Doctoral Program of Higher Education (No. 20130031110013) and the National Found for Fostering Talents of Basic Science (No. J1103306).

1. Cu(I)-Catalyzed Three-Component Reaction of Propargylic Alcohol, Secondary Amines and Atmospheric CO₂.PDF(626KB)

Abstract

β-Oxopropylcarbamates constitute an important kind of organic compounds, owing to the extensive applications in agrochemicals, pharmaceuticals, organic synthesis, and protection of amino group. In this article, an efficient and atom-economical Cu(I) catalyzed three-component reaction of propargylic alcohols, secondary amines and CO₂ has been developed under atmospheric pressure, affording various β-oxopropylcarbamates in high yields with high selectivity by controlling the concentration of O₂. This protocol avoids the use of high pressure of CO₂ and provides an extremely simple way to access the synthetically useful β-oxopropylcarbamates.

Key words: CO₂, homogeneous catalysis, synthetic methods, Cu, three-component reaction, β-oxopropylcarbamates

Cite this article

Li Xuedong, Lang Xiandong, Song Qingwen, Guo Yakun, He Liangnian. Cu(I)-Catalyzed Three-Component Reaction of Propargylic Alcohol, Secondary Amines and Atmospheric CO₂[J]. Chin. J. Org. Chem., 2016, 36(4): 744-751.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

share this article

References

[1] (a) He, L.-N. CO₂ Chemistry, Science Press, Beijing, 2013 (in Chinese). (何良年, 二氧化碳化学, 科学出版社, 北京, 2013.)
(b) Otto, A.; Grube, T.; Schiebahna, S.; Stolten, D. Energy Environ. Sci. 2015, 8, 3283.
[2] Li, J. H.; Jia, L. Q.; Jiang, H. F. Chin. J. Org. Chem. 2000, 20, 293 (in Chinese). (李金恒, 贾兰齐, 江焕峰, 有机化学, 2000, 20, 293.)
[3] (a) Sakakura, T.; Choi, J.; Yasuda, H. Chem. Rev. 2007, 107, 2365.
(b) Gao, J.; Miao, C.; Wang, J.; He, L.-N. Petrochemical Technol. 2010, 39, 465 (in Chinese). (高健, 苗成霞, 汪靖伦, 何良年, 石油化工, 2010, 39, 465.)
(c) Ji, D. F.; Lu, X. B.; He, R.; Zhan, X. L.; Yang, Y. R. Chem. J. Chin. Univ. 2001, 22, 1720 (in Chinese). (季东锋, 吕小兵, 何仁, 詹晓力, 阳永荣, 高等学校化学学报, 2001, 22, 1720.)
[4] For trepresentative reviews and reports on carbon capture and utilization, see: (a) Li, Y. N.; Ma, R.; He, L.-N.; Diao, Z. F. Catal. Sci. Technol. 2014, 4, 1498.
(b) Li, Y. N.; He, L.-N. Chin. Sci.Bull. 2015, 60, 1465 (in Chinese). (李雨浓, 何良年, 科学通报, 2015, 60, 1465.)
(c) Yang, Z. Z.; Zhao, Y. N.; He, L.-N. RSC Adv. 2011, 1, 545.
(d) Yang, Z. Z.; He, L.-N.; Zhao, Y. N.; Li, B.; Yu, B. Energy Environ. Sci. 2011, 4, 3971.
(e) Liu, A. H.; Ma, R.; Song, C.; Yang, Z. Z.; Yu, A.; Cai, Y.; He, L.-N.; Zhao, Y. N.; Yu, B.; Song, Q. W. Angew. Chem., Int. Ed. 2012, 51, 11306.
(f) Zhang, S.; Li, Y. N.; Zhang, Y. W.; He, L.-N.; Yu, B.; Song, Q. W.; Lang, X. D. ChemSusChem. 2014, 7, 1484.
[5] (a) He, M.; Sun, Y.; Han, B. Angew. Chem., Int. Ed. 2013, 52, 9620.
(b) He, M.; Sun, Y.; Han, B. Chin. Sci. Bull. 2015, 60, 1421 (in Chinese). (何鸣元, 孙予罕, 韩布兴, 科学通报, 2015, 60, 1421.)
[6] Wu, T. T.; Huang, J.; Arrington, N. D.; Dill, G. M. J. Agric. Food Chem. 1987, 35, 817.
[7] Vauthey, I.; Valot, F.; Gozzi, C.; Fache, F.; Lemaire, M. Tetrahedron Lett. 2000, 41, 6347.
[8] McGhee, W. D.; Pan, Y.; Riley, D. P. J. Chem. Soc., Chem. Commun. 1994, 6, 699.
[9] McGhee, W.; Riley, D.; Christ, K.; Pan, Y.; Parnas, B. J. Org. Chem. 1995, 60, 2820.
[10] Salvatore, R. N.; Shin, S.; Nagle, A. S.; Jung, K. W. J. Org. Chem. 2001, 66, 1035.
[11] Yoshida, M.; Hara, N.; Okuyama, S. Chem. Commun. 2000, 151.
[12] Srivastava, R.; Srinivas, D.; Ratnasamy, P. Appl. Catal. A: Gen. 2005, 289, 128.
[13] Kong, D. L.; He, L. N.; Wang, J. Q. Synth. Commun. 2011, 41, 3298.
[14] Ion, A.; Van Doorslaer, C.; Parvulescu, V.; Jacobs, P.; De Vos, D. Green Chem. 2008, 10, 111.
[15] Chaturvedi, D.; Kumar, A.; Ray, S. Tetrahedron Lett. 2003, 44, 7637.
[16] Abla, M.; Choi, J. C.; Sakakura, T. Chem. Commun. 2001, 2238.
[17] Mahe, R.; Sasaki, Y.; Bruneau, C.; Dixneuf, P. H. J. Org. Chem. 1989, 54, 1518.
[18] Selva, M.; Tundo, P.; Perosa, A. Tetrahedron Lett. 2002, 43, 1217.
[19] Dell'Amico, D. B.; Calderazzo, F.; Labella, L.; Marchetti, F.; Pampaloni, G. Chem. Rev. 2003, 103, 3857.
[20] Yang, Z. Z.; He, L. N.; Gao, J.; Liu, A. H.; Yu, B. Energy Environ. Sci. 2012, 5, 6602.
[21] Della, C. N.; Gabriele, B.; Ruffolo, G.; Veltri, L.; Zanetta, T.; Costa, M. Adv. Synth. Catal. 2011, 353, 133.
[22] Qi, C. R.; Jiang, H. F. Green Chem. 2007, 9. 1284.
[23] Sasaki, Y.; Dixncuf, P. H. J. Org. Chem. 1987, 52, 4389.
[24] Bruncau, C.; Dixncuf, P. H.; Tetrahedron Lett. 1987, 28, 2005.
[25] Qi, C. R.; Huang, L. B.; Jiang, H. F. Synthesis 2010, 1433.
[26] Kim, H. S.; Kim, J. W.; Kwon, S. C.; Shim, S. C.; Kim, T. J. J. Organomet. Chem. 1997, 545~546, 337.
[27] Kim, T. J.; Kwon, K. H.; Kwon, S. C.; Baeg, J. O.; Shim, S. C.; Lee, D. H. J. Organomet. Chem. 1990, 389, 205.
[28] Song, Q. W.; Yu, B.; Li, X. D.; Ma, R.; Diao, Z. F.; Li, R. G.; Li, W.; He, L. N. Green Chem. 2014, 16, 1633.
[29] Song, Q. W.; Chen, W. Q.; Ma, R.; Yu, A.; Li, Q. Y.; Chang, Y.; He, L. N. ChemSusChem 2015, 8, 821.
[30] Jiang, H. F.; Zhao, J. W.; Wang, A. Z. Synthesis 2008, 763.
[31] Pinaka, A.; Vougioukalakis, G. C. Coord. Chem. Rev. 2015, 288, 69.
[32] (a) Li, Y. N.; Wang, J. N.; He, L.-N. Tetrahedron Lett. 2011, 52, 3485.
(b) Yang, Z.; Wang, B.; Xu, X.; Wang, H.; Li, X. Chin. J. Org. Chem. 2015, 35, 207 (in Chinese). (杨振平, 王兵南, 许孝良, 王红, 李小年, 有机化学, 2015, 35, 207.)
[33] Hu, J.; Ma, J.; Zhu, Q.; Qian, Q.; Han, H.; Mei, Q.; Han, B. Green Chem. 2016, 18, 382.
[34] Gu, Y. L.; Shi, F.; Deng, Y. Q. J. Org. Chem. 2004, 69, 391.

铜(I)催化的常压二氧化碳、炔丙醇和仲胺三组分反应

Cu(I)-Catalyzed Three-Component Reaction of Propargylic Alcohol, Secondary Amines and Atmospheric CO₂

PDF

Supporting Info.

Knowledge

Abstract

Cite this article

share this article

References

Related Articles 15

Recommended Articles

Metrics

Comments

[1]	Simin Wu, Jiaxin Tang, Yujia Zhou, Xuetao Xu, Haoxing Zhang, Shaohua Wang. α-Glucosidase Inhibition Research of Derivatives Based on 2β-Acetoxyferruginol Scaffold Excluding Acetic Acid Group [J]. Chinese Journal of Organic Chemistry, 2024, 44(2): 613-621.
[2]	Weiqing Yang, Yanbing Ge, Yuanyuan Chen, Ping Liu, Haiyan Fu, Menglin Ma. Design and Synthesis of Fluorescent 1,8-Napthalimide Derivatives and Their Identification of Cysteine [J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 180-194.
[3]	Shan Chen, Zhilin Chen, Qiong Hu, Yanshuang Meng, Yue Huang, Pingfang Tao, Liru Lu, Guobao Huang. Recognition of Bis-thiourea Tweezers to Neutral Molecules in Non-Polar Solvent [J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 277-281.
[4]	Bozhen Wang, Jie Zhang, Chunhui Nian, Mingming Jin, Miaomiao Kong, Wulan Li, Wenfei He, Jianzhang Wu. Synthesis and Antitumor Activity of 3,4-Dichlorophenyl Amides [J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 232-241.
[5]	Shihang Yu, Jiawei Liu, Biyu An, Qinghua Bian, Min Wang, Jiangchun Zhong. Asymmetric Synthesis of the Contact Sex Pheromone of Neoclytus acuminatus acuminatus (Fabricius) [J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 301-308.
[6]	Huanqing Li, Zhaohua Chen, Zujia Chen, Qiwen Qiu, Youcai Zhang, Sihong Chen, Zhaoyang Wang. Research Progress in Mercury Ion Fluorescence Probes Based on Organic Small Molecules [J]. Chinese Journal of Organic Chemistry, 2023, 43(9): 3067-3077.
[7]	Wenjie Zhu, Zhenchuang Xu, Yu-Cheng Gu, Yanchuan Zhao. Research Progress on Organic Cation Receptors Based on Molecular Containers [J]. Chinese Journal of Organic Chemistry, 2023, 43(9): 2991-3005.
[8]	Xiaoke Zhang, Xiangru Zheng, Chaoyong Wang. Strategy to Construct Functionalized Tetrazepine Derivatives via [4+3] Annulation Reaction of Azomethine Imine with Azadiene Precursor [J]. Chinese Journal of Organic Chemistry, 2023, 43(9): 3180-3187.
[9]	Feng Wang, Yu Chen, Hongyan Pei, Jing Zhang, Lixin Zhang. Design, Synthesis and Antifungal Activities of Novel 1,2,4-Oxadiazole Derivatives Containing Piperidine [J]. Chinese Journal of Organic Chemistry, 2023, 43(8): 2826-2836.
[10]	Lu Liu, Shuguang Zhang, Renwei Hu, Xiaoxiao Zhao, Jingnan Cui, Weitao Gong. Synthesis and Properties of Phenolic Resin Polymers Based on Pillar[5]arene [J]. Chinese Journal of Organic Chemistry, 2023, 43(8): 2808-2814.
[11]	Min Liu, Dongyan Yang, Yumei Xiao, Wangcang Su, Fenghai Zhao, Qin Zhaohai .. Synthesis and Bioactivities of 5-Nitroimino-[1,4-2H]-1,2,4-triazolines as Olefin-Imidacloprid Mimics [J]. Chinese Journal of Organic Chemistry, 2023, 43(8): 2790-2799.
[12]	Li Guan, Yanyan Zhou, Yongbao Mao, Kaisen Fu, Wenhui Guan, Yile Fu. Research Progress in the Synthesis of Polymethine Chain Modified Cyanine Dyes [J]. Chinese Journal of Organic Chemistry, 2023, 43(8): 2682-2698.
[13]	Binghui Ding, Shaohui Han, Haiqing Xiong, Benhua Wang, Bojun Zuo, Xiangzhi Song. A Highly Selective Ratiometric Fluorescent Probe for the Detection of Hypochlorite in Acute Lung Injury [J]. Chinese Journal of Organic Chemistry, 2023, 43(8): 2878-2884.
[14]	Yang Zhao, Panpan Chen, Lizhi Han, Enju Wang. Aggregation-Induced Emission and Cell Imaging of Triphenylimidazole Derivatives [J]. Chinese Journal of Organic Chemistry, 2023, 43(7): 2454-2461.
[15]	Xin Zuo, Shinuo Xu, Zhongyang Chen, Jianfeng Yan, Yaofeng Yuan. Research Progress of Electron Transport Properties in Ferrocene- Containing Single-Molecule Junctions [J]. Chinese Journal of Organic Chemistry, 2023, 43(7): 2313-2322.