Ligand-Triggered, Copper Catalyzed Synthesis of Peresters and Allylic Ester from Aldehydes

doi:10.6023/cjoc201701051

Chin. J. Org. Chem. ›› 2017, Vol. 37 ›› Issue (5): 1205-1212.DOI: 10.6023/cjoc201701051 Previous Articles Next Articles

ARTICLE

配体促进下铜催化的由醛制备过酸叔丁酯及烯丙酯的反应研究

许定健, 孟力陈, 徐航, 姚小泉

南京航空航天大学材料科学与技术学院应用化学系南京 210016

收稿日期:2017-01-27 修回日期:2017-03-21 发布日期:2017-03-31
通讯作者: 姚小泉 E-mail:yaoxq@nuaa.edu.cn
基金资助:
国家自然科学基金（Nos.21472092，21172107）、江苏高校优势学科建设工程资助项目.

Ligand-Triggered, Copper Catalyzed Synthesis of Peresters and Allylic Ester from Aldehydes

Xu Dingjian, Meng Lichen, Xu Hang, Yao Xiaoquan

Department of Applied Chemistry, Nanjing University of Aeronautics and Astronautics, Nanjing 210016

Received:2017-01-27 Revised:2017-03-21 Published:2017-03-31
Contact: 10.6023/cjoc201701051 E-mail:yaoxq@nuaa.edu.cn
Supported by:
Project supported by the National Natural Science Foundation of China (Nos. 21472092, 21172107), and the Priority Academic Program Development of Jiangsu Higher Education Institutions.

1. Ligand-Triggered, Copper Catalyzed Synthesis of Peresters and Allylic Ester from Aldehydes.PDF(2839KB)

Abstract

A copper iodide catalyzed reaction of aldehydes and t-butyl hydroperoxide (TBHP) was developed for the synthesis of peresters in the presence of bipyridine ligand under mild and neat conditions. The addition of bipyridine ligand increased the catalytic activities of copper catalyst significantly and triggered the reaction. The reaction showed good tolerance to various substrates, and good to excellent yields were obtained. Furthermore, a one-pot synthesis of allylic esters was also achieved by the addition of cyclohexene to the reaction mixture under neat condition at relative lower temperature.

Key words: copper catalyzed, N-donor ligand, C-H activation, perester, allylic ester, one-pot synthesis, neat

Cite this article

Xu Dingjian, Meng Lichen, Xu Hang, Yao Xiaoquan. Ligand-Triggered, Copper Catalyzed Synthesis of Peresters and Allylic Ester from Aldehydes[J]. Chin. J. Org. Chem., 2017, 37(5): 1205-1212.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

share this article

References

[1] Some selected recent reviews: (a) Kim, D.-S.; Park, W.-J.; Jun, C.-H. Chem. Rev. 2017, DOI: 10.1021/acs.chemrev.6b00554.
(b) Liu, C.; Yuan, J.; Gao, M.; Tang, S.; Li, W.; Shi, R.; Lei, A. Chem. Rev. 2015, 115, 12138.
(c) Arockiam, P. B.; Bruneau, C.; Dixneuf, P. H. Chem. Rev. 2012, 112, 5879.
(d) Hashiguchi, B. G.; Bischof, S. M.; Konnick, M. M.; Periana, R. A. Acc. Chem. Res. 2012, 45, 885.
(e) Li, H.; Li, B.-J.; Shi, Z.-J. Catal. Sci. Technol. 2011, 2, 191.
(f) Colby, D. A.; Bergman, R. G.; Ellman, J. A. Chem. Rev. 2010, 110, 624.
(g) Lu, B.; Li, X.; Lin, Y. Chin. J. Org. Chem. 2015, 35, 2275 (in Chinese). (卢贝丽, 李现艳, 林咏梅, 有机化学, 2015, 35, 2275.)
(h) Tan, M.; Gu, Y.; Luo, X.; Zhang, P. Chin. J. Org. Chem. 2015, 35, 781 (in Chinese). (谭明雄, 顾运琼, 罗旭健, 张培, 有机化学, 2015, 35, 781.)
(i) Tang, H.; Huo, X.; Meng, Q. Acta Chim. Sinica 2016, 74, 219 (in Chinese). (汤淏溟, 霍小红, 孟庆华, 张万斌, 化学学报, 2016, 74, 219.)
(j) Some recent examples
(j) Luo, F.; Long, Y.; Li, Z.; Zhou, X. Acta Chim. Sinica 2016, 74, 805 (in Chinese). (罗飞华, 龙洋, 李正凯, 周向葛, 化学学报, 2016, 74, 805.)
(k) Cheng, Q.; Xu, H.; Zhu, S.; Zhou, Q. Acta Chim. Sinica 2015, 73, 326 (in chinese) (程清卿, 许唤, 朱守非, 周其林, 化学学报, 2015, 73, 326.)
(l) Zhang, Z.; Li, J.; Huang, G.; Sun, K.; Zhang, G.; Ma, N.; Liu, Q.; Liu, T. Chin. J. Chem. 2016, 34, 1309.
(m) Wang, L.; Li, Z.; Qu, X.; Peng, W. Chin. J. Chem. 2015, 33, 1015.
[2] Some recent examples: (a) Sarkar, S.; Laha, R. M.; Mitra, R. N.; Maiti D. K. ACS Omega 2016, 1, 981.
(b) Tang, S.; Zeng, L.; Liu, Y.; Lei, A. Angew. Chem., Int. Ed. 2015, 54, 15850.
(c) Zhou, B.; Du, J.; Yang, Y.; Li, Y. Org. Lett. 2013, 15, 2934.
(d) Sharma, S.; Park, J.; Park, E.; Kim, A.; Kim, M.; Kwak, J. H.; Jung, Y. H.; Kim, I. S. Adv. Synth. Catal. 2013, 355, 332.
[3] Some examples: (a) Mo, J.; Wang, L.; Cui, X. Org. Lett. 2015, 17, 4960.
(b) Spantulescu, M. D.; Boudreau, M. A.; Vederas, J. C. Org. Lett. 2009, 11, 645.
(c) Yamago, S. J. Polym. Sci: Polym. Chem. Ed. 2006, 44, 1.
(d) Wang, L.; Liu, X.; Li, Y. Langmuir 1998, 14, 6879.
(e) Sosnovsky, G.; Zaret, E. H.; Konieczny, M. J. Org. Chem. 1972, 37, 2267 and the references therein.
[4] Lu, M. Y.; Bao, R.; Liu, W.; Li, Y. J. Org. Chem. 1995, 60, 5341.
[5] Bolje, A.; Hohloch, S.; Urankar, D.; Pevec, A.; Gazvoda, M.; Sarkar, B.; Košmrlj, J. Organometallics 2014, 10, 2588.
[6] Zhang, H.; Dong, D.-Q.; Hao, S.-H.; Wang, Z.-L. RSC Adv. 2016, 6, 8465.
[7] Wei, W.; Zhang, C.; Xu Y.; Wan, X. Chem. Commun. 2011, 47, 10827.
[8] (a) Kharasch, M. S.; Sosnovsky, G.; Yang, N. C. J. Am. Chem. Soc. 1959, 81, 5819. For recent reviews see:
(b) Andrus, M. B.; Lashley, J. C. Tetrahedron 2002, 58, 845.
(c) Eames, J.; Watkinson, M. Angew. Chem., Int. Ed. 2001, 40, 3567.
[9] A recent review: Krylov, I. B.; Vil', V. A.; Terent'ev, A. O. Beilstein J. Org. Chem. 2015, 11, 92.
[10] Shi, E.; Shao, Y.; Chen, S.; Hu, H.; Liu, Z.; Zhang, J.; Wan, X. Org. Lett. 2012, 14, 3384.
[11] Zhou, J.; Jin, C.; Li, X.; Su, W. RSC Adv. 2015, 5, 7232.
[12] Tran, B. L.; Driess, M.; Hartwig J. F. J. Am. Chem. Soc. 2014, 136, 17292.
[13] Zhao, J.; Fang, H.; Han, J.; Pan, Y. Org. Lett. 2014, 16, 2530.
[14] Rout, S. K.; Guin, S.; Ali, W.; Gogoi, A.; Patel, B. K. Org. Lett. 2014, 16, 3086.
[15] García-Cabeza, A. L.; Marín-Barrios, R.; Moreno-Dorado, F. J.; Ortega, M. J.; Massanet, G. M.; Guerra, F. M. Org. Lett., 2014, 16, 1598.
[16] Koschker, P.; Lumbroso, A.; Breit, B. J. Am. Chem. Soc. 2011, 28, 20746.
[17] Thiery, E.; Aouf, C.; Belloy, J.; Harakat, D.; Bras, J. L.; Muzart, J. J. Org. Chem. 2010, 75, 1771.
[18] Recent reviews, see: Chem. Rev. 2008, 109(8), all of the articles therein; also see: Suzuki, M. Acc. Chem. Res. 2007, 40, 609.
[19] We also reported a series of reactions about the ligand effects on copper, silver and gold catalysts: (a) Yao, X.; Li, C.-J. Org. Lett. 2005, 7, 4395.
(b) Yao, X.; Li, C.-J. Org. Lett. 2006, 8, 1953.
(c) Yu, M.; Wang, Y.; Li, C.-J.; Yao, X. Tetrahedron Lett. 2009, 50, 6791.
(d) Han, C.; Yu, M.; Sun, W.; Yao, X. Synlett 2011, 2363.
(e) Yu, M.; Wang, Y.; Sun, W.; Yao, X. Adv. Synth. Catal. 2012, 354, 71.
(f) Wang, Y.; Wu, C.; Nie, S.; Xu, D.; Yao, X. Tetrahedron Lett. 2015, 56, 6827.

配体促进下铜催化的由醛制备过酸叔丁酯及烯丙酯的反应研究

Ligand-Triggered, Copper Catalyzed Synthesis of Peresters and Allylic Ester from Aldehydes

PDF

Supporting Info.

Knowledge

Abstract

Cite this article

share this article

References

Related Articles 15

Recommended Articles

Metrics

Comments

[1]	Wensheng Zhang, Yan Li, Haiyan Cui, Xiaoli Su, Supeng Xu. One-Pot Synthesis of N-Substituted Isoindolin-1-ones via Reductive Amination/Lactamization of Methyl 2-Formylbenzoate [J]. Chinese Journal of Organic Chemistry, 2022, 42(8): 2456-2461.
[2]	Xianghao Luo, Yibi Xie, Nianyu Huang, Long Wang. Ugi Four-Component Reaction Based on in-situ Capture of Isocyanide and Post-Modification Tandem Reaction: One-Pot Synthesis of Nitrogen Heterocycles [J]. Chinese Journal of Organic Chemistry, 2022, 42(3): 838-846.
[3]	Kaikai Wang, Shaowei Chen, Yajun Li, Daliang Li, Hongli Bao. Iron-Catalyzed Decarboxylative Heck-Type Alkylation of Conjugate 1,3-Dienes [J]. Chinese Journal of Organic Chemistry, 2021, 41(7): 2707-2714.
[4]	Jinni Liu, Yibi Xie, Qingqing Yang, Nianyu Huang, Long Wang. Ugi Four-Component Reaction Based on the in situ Capture of Amines and Subsequent Modification Tandem Cyclization Reaction: "One-Pot" Synthesis of Six- and Seven-Membered Heterocycles [J]. Chinese Journal of Organic Chemistry, 2021, 41(6): 2374-2383.
[5]	Li Huaigui, Yang Peng, Xu Zheng, Du Zhengyin, Fu Ying. Cu-Catalyzed Direct Arylation of Benzothiazoles with Diaryliodonium Salts [J]. Chinese Journal of Organic Chemistry, 2020, 40(8): 2476-2482.
[6]	Wang Hui, Wang Anwei, Xia Zhenzhen, Zhou Weiyou, Sun Zhonghua, Qian Junfeng, He Mingyang. Nickel(Ⅱ)-Catalyzed Aerobic Cross-Dehydrogenative Coupling for the Synthesis of N-Aryl Tetrahydroisoquinolines [J]. Chinese Journal of Organic Chemistry, 2020, 40(7): 2099-2107.
[7]	He Shuwang, Yan Shiqiang, Guo Wei, Zhai Guangxi, Zhang Wei. One-Pot Synthesis of Amino Alcohols from Styrenes [J]. Chinese Journal of Organic Chemistry, 2020, 40(7): 2094-2098.
[8]	Zhao Sen, Li Chunpu, Xu Bin, Liu Hong. Cp*Rh(III)-Catalyzed C—H 3,3-Difluoroallylation of Indoles and N-Iodosuccinimide-Mediated Cyclization for the Synthesis of Fluorinated 3,4-Dihydropyrimido-[1,6-a]-indol-1(2H)-one Derivatives [J]. Chinese Journal of Organic Chemistry, 2020, 40(6): 1549-1562.
[9]	Lan Jin, Xie Zongbo, Yang Jiangnan, Meng Jia, Liu Yishuai, Le Zhanggao. One-Pot Multi-component Synthesis of N,O-Acetal Compounds Catalyzed by D-Proline at Room Temperature [J]. Chinese Journal of Organic Chemistry, 2020, 40(5): 1331-1336.
[10]	Yang Kai, Yao Chen, Gao Juanjuan, Chen Sihong, Zheng Xuejie, Deng Luxuan, Zhang Yu'na, Liu Meijuan, Wang Zhaoyang. Progress on the Synthesis of Pyrido[1,2-a]benzimidazoles [J]. Chinese Journal of Organic Chemistry, 2020, 40(12): 4168-4183.
[11]	Wu Yongjie, Shi Bingfeng. Transition Metal-Catalyzed C-H Activation via Imine-Based Transient Directing Group Strategy [J]. Chinese Journal of Organic Chemistry, 2020, 40(11): 3517-3535.
[12]	Yao Biao, Wu Jiahao, Wang Yu, Jiang Huanfeng. Methods of Transition Metal-Catalyzed Asymmetric Oxidation [J]. Chinese Journal of Organic Chemistry, 2020, 40(10): 3044-3064.
[13]	Zhang Xiang, Guo Caihong, Wu Haishun. Recent Developments of Homogeneous Transition-Metal Catalysts for Low Temperature Dehydrogenation of Methanol [J]. Chin. J. Org. Chem., 2019, 39(9): 2458-2466.
[14]	Zhang Xiaopeng, Zhu Yanjie, Zhu Yisong, Li Zhengwei, Zhang Guisheng. Advances in Synthesis of 2,3-Dihydroquinazolin-4(1H)-ones [J]. Chin. J. Org. Chem., 2019, 39(9): 2392-2402.
[15]	Wan Linxi, Gao Feng, Chen Wei, Zhou Xianli. One-Pot Synthesis of 2-((2-Aminobenzoyl)amino)benzoic Acid Derivatives [J]. Chin. J. Org. Chem., 2019, 39(8): 2270-2276.