Coupling of Hantzsch Esters with Baylis-Hillman Derivatives via Visible-Light Photoredox Catalysis

doi:10.6023/cjoc201911024

Chinese Journal of Organic Chemistry ›› 2020, Vol. 40 ›› Issue (5): 1297-1304.DOI: 10.6023/cjoc201911024 Previous Articles Next Articles

Special Issue: 有机光催化虚拟合辑

可见光催化的汉斯酯和Baylis-Hillman加成物的偶联反应研究

陈跃峰^a, 赵赫^a, 程冬萍^b, 李小年^a, 许孝良^a

a 浙江工业大学化学工程学院杭州 310014;
b 浙江工业大学药学院杭州 310014

收稿日期:2019-11-19 修回日期:2020-01-17 发布日期:2020-02-15
通讯作者: 程冬萍, 李小年, 许孝良 E-mail:chengdp@zjut.edu.cn;xnli@zjut.edu.cn;xuxiaoliang@zjut.edu.cn
基金资助:
浙江省自然科学基金（Nos.LY18B020018，LY15B020004）和国家自然科学基金（No.21602197）资助项目.

Coupling of Hantzsch Esters with Baylis-Hillman Derivatives via Visible-Light Photoredox Catalysis

Chen Yuefeng^a, Zhao He^a, Cheng Dongping^b, Li Xiaonian^a, Xu Xiaoliang^a

a College of Chemical Engineering, Zhejiang University of Technology, Hangzhou 310014;
b College of Pharmaceutical Science, Zhejiang University of Technology, Hangzhou 310014

Received:2019-11-19 Revised:2020-01-17 Published:2020-02-15
Supported by:
Project supported by the Zhejiang Provincial Natural Science Foundation (Nos. LY18B020018, LY15B020004) and the National Natural Science Foundation of China (No. 21602197).

1. 201297S.pdf(715KB)

Abstract

4-Alkyl Hasntzch esters are good alkyl radical storage. The preparation of multisubstituted α,β-unsaturated carboxylic acid esters under photocatalytic redox conditions by 4-alkyl Hantzsch esters and Baylis-Hillman adducts was investigated. The reaction conditions are mild and no additional additives are required. The coupling products were obtained in moderate to good yields.

Key words: visible light photocatalysis, radical addition, Baylis-Hillman adducts, 4-alkyl Hantzsch esters

Cite this article

Chen Yuefeng, Zhao He, Cheng Dongping, Li Xiaonian, Xu Xiaoliang. Coupling of Hantzsch Esters with Baylis-Hillman Derivatives via Visible-Light Photoredox Catalysis[J]. Chinese Journal of Organic Chemistry, 2020, 40(5): 1297-1304.

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[1] (a) Chen, Y.; Lu, L. Q.; Yu, D. G.; Zhu, C. J.; Xiao, W. J. Sci. China Chem. 2019, 62, 24.
(b) Guo, W.; Tao, K.; Tan, W.; Zhao, M.; Zheng, L.; Fan, X. Org. Chem. Front. 2019, 6, 2048.
(c) Yi, H.; Zhang, G.; Wang, H.; Huang, Z.; Wang, J.; Singh, A. K.; Lei, A. Chem. Rev. 2017, 117, 9016.
(d) Qiu, G.; Li, Y.; Wu, J. Org. Chem. Front. 2016, 3, 1011.
(e) Chen, J.; Cen, J.; Xu, X.; Li, X. Catal. Sci. Technol. 2016, 6, 349.
(f) Xiao, L.; Li, J.; Wang, T. Acta Chim. Sinica 2019, 77, 841(in Chinese). (肖丽, 李嘉恒, 王挺, 化学学报, 2019, 77, 841.)
(g) Chen, D.; Liu, J.; Zhang, X.; Jiang, H.; Li, J. Chin. J. Org. Chem. 2019, 39, 3353(in Chinese). (陈丹, 刘剑沉, 张馨元, 蒋合众, 李加洪, 有机化学, 2019, 39, 3353.)
[2] (a) Zheng, C.; You, S. L. Chem. Soc. Rev. 2012, 41, 2498.
(b) Qi, L.; Chen, Y. Angew. Chem., Int. Ed. 2016, 55, 13312.
(c) Rono, L. J.; Yayla, H. G.; Wang, D. Y.; Armstrong, M. F.; Knowles, R. R. J. Am. Chem. Soc. 2013, 135, 17735.
(d) Larraufie, M. H.; Pellet, R.; Fensterbank, L.; Goddard, J. P.; Lacôte, E.; Malacria, M.; Ollivier, C. Angew. Chem., Int. Ed. 2011, 50, 4463.
(e) Zhang, J.; Li, Y.; Zhang, F.; Hu, C.; Chen, Y. Angew. Chem., Int. Ed. 2016, 55, 1872.
(f) Lee, K. N., Lei, Z.; Ngai, M. Y. J. Am. Chem. Soc. 2017, 139, 5003.
(g) Wang, P. Z.; Chen, J. R. Xiao, W. J. Org. Biomol. Chem. 2019, 17, 6936.
[3] (a) Li, G.; Wu, L.; Lv, G.; Liu, H.; Fu, Q.; Zhang, X.; Tang, Z. Chem. Commun. 2014, 50, 6246.
(b) Chen, W.; Liu, Z.; Tian, J.; Li, J.; Ma, J.; Cheng, X.; Li, G. J. Am. Chem. Soc. 2016, 138, 12312.
(c) Liu, X.; Liu, R.; Dai, J.; Cheng, X.; Li, G. Org. Lett. 2018, 20, 6906.
(d) Zhang, H. H.; Zhao, J. J.; Yu, S. J. Am. Chem. Soc. 2018, 140, 16914.
(e) Wu, Q. Y.; Min, Q. Q.; Ao, G. Z.; Liu, F. Org. Biomol. Chem. 2018, 16, 6391.
(f) Zhang, H. H.; Yu, S. J. Org. Chem. 2017, 82, 9995.
(g) Gu, F.; Huang, W.; Liu, X.; Chen, W.; Cheng, X. Adv. Synth. Catal. 2018, 360, 925.
[4] (a) Nakajima, K.; Nojima, S.; Sakata, K.; Nishibayashi, Y. ChemCatChem 2016, 8, 1028.
(b) Gutiérrez-Bonet, A.; Tellis, J. C.; Matsui, J. K.; Vara, B. A.; Molander, G. A. ACS Catal. 2016, 6, 8004.
[5] Song, Z. Y.; Zhang, C. L.; Ye, S. Org. Biomol. Chem. 2019, 17, 181.
[6] (a) Reddy, T. N.; Rao, V. J. Tetrahedron Lett. 2018, 59, 2859.
(b) Yadav, A. K.; Sharma, A. K.; Singh, K. N. Org. Chem. Front. 2019, 6, 989.
(c) Basavaiah, D.; Reddy, B. S.; Badsara, S. S. Chem. Rev. 2010, 110, 5447.
(d) Liu, T. Y.; Xie, M.; Chen, Y. C. Chem. Soc. Rev. 2012, 41, 4101.
(e) Trost, B. M.; Brennan, M. K. Org. Lett. 2007, 9, 3961.
[7] (a) Ye, H.; Ye, Q.; Cheng, D.; Li, X.; Xu, X. Tetrahedron Lett. 2018, 59, 2046.
(b) Ye, H.; Zhao, H.; Ren, S.; Ye, H.; Cheng, D.; Li, X.; Xu, X. Tetrahedron Lett. 2019, 60, 1302.
(c) Dai, X.; Cheng, D.; Guan, B.; Mao, W.; Xu, X.; Li, X. J. Org. Chem. 2014, 79, 7212.
(d) Dai, X.; Mao, R.; Guan, B.; Xu, X.; Li, X. RSC Adv. 2015, 5, 55290.
(e) Guan, B.; Xu, X.; Wang, H.; Li, X.; Chin. J. Org. Chem. 2016, 36, 1564(in Chinese). (关宝川, 许孝良, 王红, 李小年, 有机化学, 2016, 36, 1564.)
(f) Dai, X.; Xu, X.; Li, X.; Chin. J. Org. Chem. 2013, 33, 2046(in Chinese). (戴小军, 许孝良, 李小年, 有机化学, 2013, 33, 2046.)
[8] Li, G.; Chen, R.; Wu, L.; Fu, Q.; Zhang, X.; Tang, Z. Angew. Chem., Int. Ed. 2013, 52, 8432.
[9] Companyó, X.; Geant, P. Y.; Mazzanti, A.; Moyano, A.; Rios, R. Tetrahedron 2014, 70, 75.

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可见光催化的汉斯酯和Baylis-Hillman加成物的偶联反应研究

Coupling of Hantzsch Esters with Baylis-Hillman Derivatives via Visible-Light Photoredox Catalysis

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