Palladium-Catalyzed Intermolecular Carboesterification of Alkynoic Acids with Alkenes

doi:10.6023/cjoc201505033

Chin. J. Org. Chem. ›› 2015, Vol. 35 ›› Issue (10): 2199-2204.DOI: 10.6023/cjoc201505033 Previous Articles Next Articles

Notes

钯催化炔酸与烯烃串联碳酯化反应研究

李建晓^a, 张振明^a, 李春生^a, 罗维^b, 杨少容^a

a 华南理工大学化学与化工学院广州 510640;
b 华南理工大学分析测试中心广州 510640

收稿日期:2015-05-21 修回日期:2015-06-05 发布日期:2015-06-16
通讯作者: 杨少容 E-mail:lisryang@scut.edu.cn
基金资助:
国家自然科学基金(Nos. 21102047, 31101221)和中国博士后科学基金(No. 2015M572303)资助项目.

Palladium-Catalyzed Intermolecular Carboesterification of Alkynoic Acids with Alkenes

Li Jianxiao^a, Zhang Zhenming^a, Li Chunsheng^a, Luo Wei^b, Yang Shaorong^a

a School of Chemistry and Chemical Engineering, South China University of Technology, Guangzhou 510640;
b Analytical and Testing Center, South China University of Technology, Guangzhou 510640

Received:2015-05-21 Revised:2015-06-05 Published:2015-06-16
Supported by:
Project supported by the National Natural Science Foundation of China (Nos. 21102047, 31101221) and the China Postdoctoral Science Foundation (No. 2015M572303).

1. Palladium-Catalyzed Intermolecular Carboesterification of Alkynoic Acids with Alkenes.PDF(678KB)

Abstract

An efficient and mild palladium-catalyzed cascade carboesterification has been developed to afford functionalized α-methylene-γ-lactones in moderate to good yields with high regio-and diastereo-selectivities. Their structures were confirmed by IR, ¹H NMR, ¹³C NMR and HRMS. Furthermore, this reaction provided a novel and convenient methodology for the construction of naturally occurring biologically active α-methylene-γ-lactones.

Key words: palladium-catalyzed, ionic liquids, alkynoic acids, alkenes, carboesterification

Cite this article

Li Jianxiao, Zhang Zhenming, Li Chunsheng, Luo Wei, Yang Shaorong. Palladium-Catalyzed Intermolecular Carboesterification of Alkynoic Acids with Alkenes[J]. Chin. J. Org. Chem., 2015, 35(10): 2199-2204.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

share this article

References

[1] (a) McDonald, R. I.; Liu, G.; Stahl, S. S. Chem. Rev. 2011, 111, 2981. (b) Merino, E.; Nevado, C. Chem. Soc. Rev. 2014, 43, 6598.
[2] (a) Wang, F.; Wang, D.; Mu, X.; Chen, P.; Liu, G. J. Am. Chem. Soc. 2014, 136, 10202. (b) Hu, M.; Song, R.-J.; Li, J.-H. Angew. Chem., Int. Ed. 2015, 54, 608.
[3] Muniz, K.; Hovelmann, C. H.; Streuff, J. J. Am. Chem. Soc. 2008, 130, 763.
[4] Wickens, Z. K.; Guzmán, P. E.; Grubbs, R. H. Angew. Chem., Int. Ed. 2015, 54, 236.
[5] Wang, A.; Jiang, H. J. Org. Chem. 2010, 75, 2321.
[6] Zhang, Z.; Ouyang, L.; Wu, W.; Li, J.; Zhang, Z.; Jiang, H. J. Org. Chem. 2014, 79, 10734.
[7] Hyster, T. K.; Dalton, D. M.; Rovis, T. Chem. Sci. 2015, 6, 254.
[8] Wu, T.; Mu, X.; Liu, G. Angew. Chem., Int. Ed. 2011, 50, 12578.
[9] Sehnal, P.; Taylor, R. J. K.; Fairlamb, I. J. S. Chem. Rev. 2010, 110, 824.
[10] Peng, H.; Liu, G. Org. Lett. 2011, 13, 772.
[11] Park, C. P.; Lee, J. H.; Yoo, K. S.; Jung, K. W. Org. Lett. 2010, 12, 2450.
[12] Kitson, R. R. A.; Millemaggi, A.; Taylor, R. J. K. Angew. Chem., Int. Ed. 2009, 48, 9426.
[13] Albrecht, A.; Albrecht, ?.; Janecki, T. Eur. J. Org. Chem. 2011, 2747.
[14] (a) Zhu, G.; Lu, X. J. Org. Chem. 1995, 60, 1087. (b) Zhang, Q.; Lu, X. J. Am. Chem. Soc. 2000, 122, 7604.
[15] Lei, A.; He, M.; Zhang, X. J. Am. Chem. Soc. 2002, 124, 8198.
[16] (a) Huang, L.; Wang, Q.; Liu, X.; Jiang, H. Angew. Chem., Int. Ed. 2012, 51, 5696. (b) Zhang, Z.; Wu, W.; Liao, J.; Li, J.; Jiang, H. Chem. Eur. J. 2015, 21, 6708.
[17] (a) Wu, W.; Jiang, H. Acc. Chem. Res. 2012, 45, 1736. (b) Wu, W.; Jiang, H. Acc. Chem. Res. 2014, 47, 2483.
[18] (a) Li, J.; Yang, S.; Jiang, H.; Wu, W.; Zhao, J. J. Org. Chem. 2013, 78, 12477. (b) Li, J.; Yang, S. Chin. J. Org. Chem. 2013, 33, 2407 (in Chinese). (李建晓, 杨少容, 有机化学, 2013, 33, 2407.) (c) Yang, S.; Ling, C.; Ma, J.; Zhang, L.; Li, J.; Luo, W. Chin. J. Org. Chem. 2014, 34, 1148 (in Chinese). (杨少容, 凌厂围, 马建业, 张蕾, 李建晓, 罗维, 有机化学, 2014, 34, 1148.) (d) Li, J.; Yang, S.; Wu, W.; Jiang, H. Chem. Commun. 2014, 50, 1381. (e) Li, J.; Yang, W.; Yang, S.; Huang, L.; Wu, W.; Sun, Y.; Jiang, H. Angew. Chem. Int. Ed. 2014, 53, 7219. (f) Li, J.; Li, C.; Yang, S.; Luo, W. Chin. J. Org. Chem. 2015, 35, 898 (in Chinese). (李建晓, 李春生, 杨少容, 罗维, 有机化学, 2015, 35, 898.) (g) Li, J.; Zhu, Z.; Yang, S.; Zhang, Z.; Wu, W.; Jiang, H. J. Org. Chem. 2015, 80, 3870.
[19] Huddleston, J. G.; Willauer, H. D.; Swatloski, R. P.; Visser, A. E.; Rogers, R. D. Chem. Commun. 1998, 1765;
[20] Park, S.; Kazlauskas, R. J. J. Org. Chem. 2001, 66, 8395.
[21] Branco, L. C.; Rosa, J. N.; Ramos, J. J. M.; Afonso, C. A. M. Chem. Eur. J. 2002, 8, 3671.
[22] Miao, C. X.; He, L. N.; Wang, J. Q.; Wang, J. L. Adv. Synth. Catal. 2009, 351, 2209.

钯催化炔酸与烯烃串联碳酯化反应研究

Palladium-Catalyzed Intermolecular Carboesterification of Alkynoic Acids with Alkenes

PDF

Supporting Info.

Knowledge

Cited

Abstract

Cite this article

share this article

References

Related Articles 15

Recommended Articles

Metrics

Comments

[1]	Sida Li, Xing-Zhong Shu, Lipeng Wu. Zirconium and Titanium Mediated Hydroboration of Alkenes and Alkynes [J]. Chinese Journal of Organic Chemistry, 2023, 43(5): 1751-1760.
[2]	Jiajie Zhu, Yi Wan, Qiyang Yuan, Jinlian Wei, Yongqiang Zhang. Research of Visible Light/Lewis Base Dual Catalytic Defluorinative Silylation of Trifluoromethyl-Substituted Alkenes [J]. Chinese Journal of Organic Chemistry, 2023, 43(10): 3623-3634.
[3]	Yan Huang, Qian Zhang, Lewu Zhan, Jing Hou, Bindong Li. Hydrocarboxylation of Alkenes with Formate Salts via Photocatalysis [J]. Chinese Journal of Organic Chemistry, 2022, 42(8): 2568-2573.
[4]	Yazhou Wang, Yuhang Zhu, Lixia Xu, Rui He, Jian Zhang. Recent Advances in Geminal-Group-Directed Alkenyl C—H Functionalization [J]. Chinese Journal of Organic Chemistry, 2022, 42(7): 2000-2014.
[5]	Duoduo Xiao, Hailing Liu, Peng Zhou, Jiantao Zhang, Weibing Liu. I₂/t-Butylhydroperoxide (TBHP)-Mediated Oxo-amidation of Alkenes with N,N-Dimethylformamide: A Facile Access to Aryl-α-ketoamide Derivatives [J]. Chinese Journal of Organic Chemistry, 2022, 42(5): 1438-1442.
[6]	Xiuying Li, Pingfang Tao, Yongyu Cheng, Qiong Hu, Weijuan Huang, Yun Li, Zhihui Luo, Guobao Huang. Recent Progress on the Electrochemical Difunctionalization of Alkenes/Alkynes [J]. Chinese Journal of Organic Chemistry, 2022, 42(12): 4169-4201.
[7]	Lüyin Zheng, Yihan Wang, Liuhuan Cai, Wei Guo. Progress in C—CF₃/C—N Bond Formation Reactions of Alkenes Involving in Free Radicals [J]. Chinese Journal of Organic Chemistry, 2022, 42(12): 4078-4098.
[8]	Junfei Li, Yuling Han, Yanhong Liu, Jianxin Chen. Synthesis of β-Nitroamide Derivatives Based on Carbamoylsilane [J]. Chinese Journal of Organic Chemistry, 2022, 42(11): 3880-3889.
[9]	Haorui Wang, Mengchun Ye. Research Advance on Enantioselective Transition Metal-Catalyzed Hydroacylation Reactions [J]. Chinese Journal of Organic Chemistry, 2022, 42(10): 3152-3166.
[10]	Yuanyuan Ping, Haixia Song, Wangqing Kong. Recent Advances in Ni-Catalyzed Asymmetric Reductive Difunctionalization of Alkenes [J]. Chinese Journal of Organic Chemistry, 2022, 42(10): 3302-3321.
[11]	Yang Han, Weichao Jiang, Jing Zhang, Jinsong Peng, Chunxia Chen. Visible-Light-Promoted Palladium-Catalyzed C—H Amination for the Synthesis of Carbazolequinones [J]. Chinese Journal of Organic Chemistry, 2022, 42(1): 266-276.
[12]	Yunshuai Huang, Xiaohui Jin, Fenglian Zhang, Yifeng Wang. 4-Dimethylaminopyridine-Boryl Radical Promoted Regioselective Radical Hydroboration of Electron-Deficient Alkenes [J]. Chinese Journal of Organic Chemistry, 2021, 41(5): 1957-1967.
[13]	Lingling Zhang, Zhi Wang, Jian Wu, Xiaoqing Li. Synthesis of Nitro-Functionalized Isoquinolinediones via NaNO₂/Na₂S₂O₈-Mediated Arylnitration of Alkenes [J]. Chinese Journal of Organic Chemistry, 2021, 41(4): 1734-1738.
[14]	Honglei Jin, Fengxuan Jiang, Kai Cheng, Lehao Huang. Palladium-Catalyzed C8 Alkylation of 1-Naphthylamides and Its Application to the Synthesis of the Core Sturctures of Aporphine and Aristolactam Alkaloids [J]. Chinese Journal of Organic Chemistry, 2021, 41(4): 1691-1702.
[15]	Xin Xi, Gongping Zhang, Jiancheng Li, Yanting Huang, Wenjun Jiang, Peng Wu, Hongping Zhu. Synthesis of Alkynes Composed of the Novel Substituents and Their Reactions with B(C₆F₅)₃ [J]. Chinese Journal of Organic Chemistry, 2021, 41(2): 766-775.