Chloropalladation Triggering the Cascade Annulation to Construct Functionalized Saturated γ-Lactones in Ionic Liquids

doi:10.6023/cjoc201411026

Chin. J. Org. Chem. ›› 2015, Vol. 35 ›› Issue (4): 898-904.DOI: 10.6023/cjoc201411026 Previous Articles Next Articles

Notes

离子液体中氯钯化启动的串联环化构建饱和γ-丁内酯反应研究

李建晓^a, 李春生^a, 杨少容^a, 罗维^b

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:2014-11-14 修回日期:2014-12-03 发布日期:2014-12-15
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)资助项目.

Chloropalladation Triggering the Cascade Annulation to Construct Functionalized Saturated γ-Lactones in Ionic Liquids

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

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:2014-11-14 Revised:2014-12-03 Published:2014-12-15
Supported by:
Project supported by the National Natural Science Foundation of China (Nos. 21102047, 31101221).

1. Chloropalladation Triggering the Cascade Annulation to Construct Functionalized Saturated γ-Lactones in Ionic Liquids.PDF(891KB)

Abstract

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

Key words: ionic liquids, chloropalladation, alkynes, pent-4-enoic acid, saturated γ-lactones

Cite this article

Li Jianxiao, Li Chunsheng, Yang Shaorong, Luo Wei. Chloropalladation Triggering the Cascade Annulation to Construct Functionalized Saturated γ-Lactones in Ionic Liquids[J]. Chin. J. Org. Chem., 2015, 35(4): 898-904.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

share this article

References

[1] (a) Gooβen, L. J.; Ohlmanna, D. M.; Dierker, M. Green Chem. 2010, 12, 197.
(b) Devalankar, D. A.; Karabal, P. U.; Sudalai, A. Org. Biomol. Chem. 2013, 11, 1280.
[2] (a) Tener, G. M.; van Tamelen, E. E.; Strong, F. M. J. Am. Chem. Soc. 1953, 75, 3623.
(b) He, M.; Lei, A.; Zhang, X. Tetrahedron Lett. 2005, 46, 1823.
(c) Albrecht, A.; Albrecht, L.; Janecki, T. Eur. J. Org. Chem. 2011, 2747.
(d) Woods, J. R.; Mo, H.; Bieberich, A. A.; Alavanja, T.; Colby, D. A. Med. Chem. Commun. 2013, 4, 27.
[3] (a) Bandichhor, R.; Nosse, B.; Reiser, O. Top. Curr. Chem. 2005, 243, 43.
(b) Kitson, R. R. A.; Millemaggi, A.; Taylor, R. J. K. Angew. Chem., Int. Ed. 2009, 48, 9426.
[4] (a) Yoda, H.; Shirakawa, K.; Takabe, K. Tetrahedron Lett. 1991, 32, 3401.
(b) Takahata, H.; Uchida, Y.; Momose, T. J. Org. Chem. 1994, 59, 7201.
(c) Berkenbusch, T.; Bruckner, R. Tetrahedron 1998, 54, 11461.
(d) Greatrex, B. W.; Kimber, M. C.; Taylor, D. K.; Fallon, G.; Tiekink, E. R. T. J. Org. Chem. 2002, 67, 5307.
(e) Liu, G.; Lu, X. Tetrahedron Lett. 2003, 44, 127.
(f) Huang, L.; Jiang, H.; Qi, C.; Liu, X. J. Am. Chem. Soc. 2010, 132, 17652.
(g) Zhou, L.; Tan, C. K.; Jiang, X.; Chen, J. F.; Yeung, Y. Y. J. Am. Chem. Soc. 2010, 132, 15474.
[5] Beller, M.; Bolm, C. Transition Metals for Organic Synthesis, Wiley-VCH, Weinheim, Germany, 2004.
[6] Oliveira, C. C.; Angnes, R. A.; Correia, C. R. D. J. Org. Chem. 2013, 78, 4373.
[7] Shu, C.; Liu, M. Q.; Sun, Y. Z.; Ye, L. W. Org. Lett. 2012, 14, 4958.
[8] Steward, K. M.; Gentry, E. C.; Johnson, J. S. J. Am. Chem. Soc. 2012, 134, 7329.
[9] Kramer, J. W.; Joh, D. Y.; Coates, G. W. Org. Lett. 2007, 9, 5581.
[10] (a) Horváth, I. T.; Anastas, P. T. Chem. Rev. 2007, 107, 2169.
(b) Gunanathan, C.; Milstein, D. Acc. Chem. Res. 2011, 44, 588.
(c) Sundararaju, B.; Achard, M.; Bruneau, C. Chem. Soc. Rev. 2012, 41, 4467.
[11] Lu, X. Y. Prog. Chem. 1998, 10, 123 (in Chinese).
(陆熙炎, 化学进展, 1998, 10, 123.)
[12] (a) Lindstroem, U. M. Chem. Rev. 2002, 102, 2751.
(b) Li, C. J.; Chen, J. Chem. Soc. Rev. 2006, 35, 68.
[13] Leitner, W. Acc. Chem. Res. 2002, 35, 746.
[14] Horváth, I. T. Acc. Chem. Res. 1998, 31, 641.
[15] Zhang, S. B.; Ding, M. X.; Gao, L. X. Chin. J. Org. Chem. 2002, 22, 159 (in Chinese).
(张锁波, 丁孟贤, 高连勋, 有机化学, 2002, 22, 159.)
[16] (a) Welton, T. Chem. Rev. 1999, 99, 2071.
(b) Dupont, J.; Souza, R. F.; Suarez, P. A. Z. Chem. Rev. 2002, 102, 3667.
[17] Deng, Y. Q. Ionic Liquids-Properties Preparation and Application, China Petrochemical Press, Beijing, 2006 (in Chinese).
(邓友全, 离子液体-性质制备与应用, 中国石化出版社, 北京, 2006.)
[18] (a) Yang, S.; Jiang, H.; Chen, H.; Xu, Y.; Luo, W. Synth. Commun. 2007, 37, 2121.
(b) Yang, S.; Jiang, H.; Li, Y.; Chen, H.; Luo, W.; Xu, Y. Tetrahedron 2008, 64, 2930.
(c) Li, J.; Yang, S.; Huang, L.; Chen, H.; Jiang, H. RSC Adv. 2013, 3, 11529.
(d) Li, J.; Yang, S.; Jiang, H.; Wu, W.; Zhao, J. J. Org. Chem. 2013, 78, 12477.
(e) 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.)
(f) 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.)
(g) Li, J.; Yang, S.; Wu, W.; Qi, C.; Deng, Z.; Jiang, H. Tetrahedron 2014, 70, 1516.
(h) Li, J.; Yang, S.; Wu, W.; Jiang, H. Chem. Commun. 2014, 50, 1381.
(i) Li, J.; Yang, W.; Yang, S.; Huang, L.; Wu, W.; Sun, Y.; Jiang, H. Angew. Chem., Int. Ed. 2014, 53, 7219.
[19] (a) Wu, W.; Jiang, H. Acc. Chem. Res. 2012, 45, 1736.
(b) Wu, W.; Jiang, H. Acc. Chem. Res. 2014, 47, 2483.
[20] Huddleston, J. G.; Willauer, H. D.; Swatloski, R. P.; Visser, A. E.; Rogers, R. D. Chem. Commun. 1998, 1765;
[21] Park, S.; Kazlauskas, R. J. J. Org. Chem. 2001, 66, 8395.
[22] Chum, H. L.; Koch, V. R.; Miller, L. L.; Osteryoung, R. A. J. Am. Chem. Soc. 1975, 97, 3264.
[23] Branco, L. C.; Rosa, J. N.; Ramos, J. J. M.; Afonso, C. A. M. Chem. Eur. J. 2002, 8, 3671.
[24] Miao, C. X.; He, L. N.; Wang, J. Q.; Wang, J. L. Adv. Synth. Catal. 2009, 351, 2209.

离子液体中氯钯化启动的串联环化构建饱和γ-丁内酯反应研究

Chloropalladation Triggering the Cascade Annulation to Construct Functionalized Saturated γ-Lactones in Ionic Liquids

PDF

Supporting Info.

Knowledge

Abstract

Cite this article

share this article

References

Related Articles 15

Recommended Articles

Metrics

Comments

[1]	Wenfeng Bei, Jian Pan, Dongmei Ran, Yilin Liu, Zhen Yang, Ruokun Feng. Cobalt-Catalyzed [4+2] Annulation of Indole Carboxamide with Diynes and Monoacetylene: Direct Access to γ-Carbolinones [J]. Chinese Journal of Organic Chemistry, 2023, 43(9): 3226-3238.
[2]	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.
[3]	Peng Liu, Fuming Zhong, Lihao Liao, Weiqiang Tan, Xiaodan Zhao. Progress in the Construction of Spirocyclohexadienones via Alkyne-Involving Dearomatization [J]. Chinese Journal of Organic Chemistry, 2023, 43(12): 4019-4035.
[4]	Chong Tian, Qi Sun, Junfeng Wang, Qiao Chen, Zhiguo Wen, Maxim Borzov, Wanli Nie. E-Stereospecific 1,1-Carboboration of Terminal Arylalkynes with [IB(C₆F₅)₃]^– [J]. Chinese Journal of Organic Chemistry, 2023, 43(1): 338-344.
[5]	Qi Sun, Zeying Sun, Ze Yu, Guangwei Wang. Nickel-Catalyzed Stereoselective Aryl-Difluoroalkylation of Alkynes [J]. Chinese Journal of Organic Chemistry, 2022, 42(8): 2515-2520.
[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]	Gaige Zhu, Xiaohui Lai, Siyu Wang, Caixia Lin, Yaofeng Yuan. Synthesis of 2-Imino-1,2-dihydroquinolines via Copper Catalysis [J]. Chinese Journal of Organic Chemistry, 2021, 41(7): 2810-2819.
[8]	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.
[9]	Xin Wang, Yan Zhang, Kai Sun, Jianping Meng, Bing Zhang. Study on the Application of Photoelectric Technology in the Synthesis of Selenium-Containing Heterocycles [J]. Chinese Journal of Organic Chemistry, 2021, 41(12): 4588-4609.
[10]	Zihui Ning, Xinhua Peng, Rui Bai, Shanshan Liu, Zhuo Li, Linyu Jiao. Iridium Catalyzed C—H Amidation of Benzamides with Phosphoryl Azides in Ionic Liquids [J]. Chinese Journal of Organic Chemistry, 2021, 41(11): 4484-4492.
[11]	Sun Mingli, Zhang Jiajun, Zhang Yicheng, Li Pinhua, Wang Lei. A Silver-Catalyzed Functionalization of 1-Bromoalkynes: Highly Regio-and Stereo-selective Synthesis of (Z)-β-Bromo-1-arylvinyl Aryl Esters [J]. Chinese Journal of Organic Chemistry, 2020, 40(8): 2419-2425.
[12]	Li Shengnan, Zhao Wenxin, Liu Yujing, Liu Zhongqiu, Ying Anguo. Research Progress in the Application of Supported Functional Ionic Liquids in Organic Transformations [J]. Chinese Journal of Organic Chemistry, 2020, 40(7): 1835-1846.
[13]	Zhang Lei, Yuan Sitian, Wang Peng, Liu Jinbiao. Recent Advances in Cyclization Reaction of Alkynes under Transition Metal-Free Conditions [J]. Chinese Journal of Organic Chemistry, 2020, 40(6): 1529-1539.
[14]	Lu Lingling, Li Yiming, Jiang Xuefeng. Visible-Light-Promoted Diiodination of Alkynes Using Sodium Iodide [J]. Chinese Journal of Organic Chemistry, 2020, 40(10): 3354-3361.
[15]	Zheng Renhua, Guo Haichang, Yang Mingyang, Liu Mengqi, Ye Longwu. 1,4-Functionalization of 3-En-1-ynes with Alcohols via Zinc-Catalyzed Regioselective N-Oxide Oxidation [J]. Chin. J. Org. Chem., 2019, 39(6): 1672-1680.