银催化的脱羧性偶联反应研究进展
收稿日期: 2018-05-03
修回日期: 2018-06-11
网络出版日期: 2018-07-16
基金资助
国家自然科学基金（No.21402123）、浙江省自然科学基金（No.LY18B020006，LQ15B020002）和绍兴市科技计划（No.2017B70053）资助项目.
Research Progress on Silver-Catalyzed Decarboxylative Coupling Reaction
Received date: 2018-05-03
Revised date: 2018-06-11
Online published: 2018-07-16
Supported by
Project supported by the National Natural Science Foundation of China (No. 21402123), the Zhejiang Provincial Natural Science Foundation (No. LY18B020006, LQ15B020002) and the Science Technology Project of Shaoxing City (No. 2017B70053).
殷晓婷 , 李文炅 , 赵保丽 , 程凯 . 银催化的脱羧性偶联反应研究进展[J]. 有机化学, 2018 , 38(11) : 2879 -2887 . DOI: 10.6023/cjoc201805013
Transition-metal-catalyzed decarboxylative cross-coupling reactions have been well developed as efficient synthetic methods in organic synthesis. Herein the new application of silver-catalyzed decarboxylation in Hunsdiecker-type halogenation, carbon-carbon bond formation, carbon-heteratom bond formation and C-H bond functionalization reaction is discussed. The recent progress in silver-catalyzed decarboxylative coupling reaction with aliphatic carboxylic acids, α-keto acids and aryl carboxylic acid is reviewed. With the assistance of peroxides, selective decarboxylative coupling reaction could be proceeded via free-radical process by silver catalysis. The controlled free-radical transformation is operational simplification without the exclusion of water and oxygen under mild conditions.
[1] Zhang, Y.; Luo, S.; Zhu, C. J. Chin. J. Org. Chem. 2012, 32, 2073(in Chinese). (张艳, 罗莎, 朱成建, 有机化学, 2012, 32, 2073.)
[2] Cheng, Y.; Sun, L. P. Chin. J. Org. Chem. 2013, 33, 877(in Chinese). (成宜娟, 孙丽萍, 有机化学, 2013, 33, 877.)
[3] Zheng, Q.-Z.; Jiao, N. Chem. Soc. Rev. 2016, 45, 4590.
[4] Dai, J.-J.; Wang, G. Z.; Xu, X. L.; Xu, H. J. Chin. J. Org. Chem. 2013, 33, 2460(in Chinese). (戴建军, 王光祖, 徐小岚, 许华建, 有机化学, 2013, 33, 2460.)
[5] Fu, Z.-J.; Li, Z. J.; Xiong, Q. H.; Cai, H. Chin. J. Org. Chem. 2015, 35, 984(in Chinese). (付拯江, 李兆杰, 熊起恒, 蔡琥, 有机化学, 2015, 35, 984.)
[6] Guan, B.-C.; Xu, X. L.; Wang, H.; Li, X. N. Chin. J. Org. Chem. 2016, 36, 1564(in Chinese). (关保川, 许孝良, 王红, 李小年, 有机化学, 2016, 36, 1564.)
[7] Wang, Z.; Zhu, L.; Yin, F.; Su, Z.; Li, Z.; Li, C. J. Am. Chem. Soc. 2012, 134, 4258.
[8] Tan, X.; Song, T.; Wang, Z.; Chen, H.; Cui, L.; Li, C. Org. Lett. 2017, 19, 1634.
[9] Yin, F.; Wang, Z.; Li, Z.; Li, C. J. Am. Chem. Soc. 2012, 134, 10401.
[10] Mizuta, S.; Stenhagen, I. S. R.; O'Duill, M.; Wolstenhulme, J.; Kirjavainen, A. K.; Forsback, S. J.; Tredwell, M.; Sandford, G.; Moore, P. R.; Huiban, M.; Luthra, S. K.; Passchier, J.; Solin, O.; Gouverneur, V. Org. Lett. 2013, 15, 2648.
[11] Zhang, Q.-W.; Brusoe, A. T.; Mascitti, V.; Hesp, K. D.; Blakemore, D. C.; Kohrt, J. T.; Hartwig, J. F. Angew. Chem., Int. Ed. 2016, 55, 9758.
[12] Patel, N. R.; Flowers, R. A. J. Org. Chem. 2015, 80, 5834.
[13] Hua, A. M.; Mai, D. N.; Martines, R.; Baxter, R. D. Org. Lett. 2017, 19, 2949.
[14] Liu, X.; Wang, Z.; Cheng, X.; Li, C. J. Am. Chem. Soc. 2012, 134, 14330.
[15] Chen, F.; Hashmi, S. K. Org. Lett. 2016, 18, 2880.
[16] Mai, W. P.; Song, G.; Sun, G. C.; Yang, L. R.; Yuan, J. W.; Xiao, Y. M.; Mao, P.; Qu, L. B. RSC Adv. 2013, 3, 19264.
[17] Cui, L.; Chen, H.; Liu, C.; Li, C. Org. Lett. 2016, 18, 2188.
[18] Zhu, Y.; Wen, X.; Song, S.; Jiao, N. ACS Catal. 2016, 6, 6465.
[19] Xia, X. F.; Zhu, S. L.; Chen, C.; Wang, H.; Liang, Y. M. J. Org. Chem. 2016, 81, 1277.
[20] Tan, X.; Liu, Z.; Shen, H.; Zhang, P.; Zhang, Z.; Li, C. J. Am. Chem. Soc. 2017, 139, 12430.
[21] Zhu, Y.; Li, X.; Wang, X.; Huang, X.; Shen, T.; Zhang, Y.; Sun, X.; Zou, M.; Song, S.; Jiao, N. Org. Lett. 2015, 17, 4702.
[22] Liu, C.; Wang, X.; Li, Z.; Cui, L.; Li, C. J. Am. Chem. Soc. 2015, 137, 9820.
[23] Hu, F.; Shao, X.; Zhu, D.; Lu, L.; Shen, Q. Angew. Chem., Int. Ed. 2014, 53, 6105.
[24] He, B.; Xiao, Z.; Wu, H.; Guo, Y.; Chen, Q. Y.; Liu, C. RSC Adv. 2017, 7, 880.
[25] Wang, P.-F.; Wang, X. Q.; Dai, J. J.; Feng, Y. S.; Xu, H. J. Org. Lett. 2014, 16, 4586.
[26] Wang, W.; Liu, X.; Wang, X. ChemistrySelect 2017, 2, 1140.
[27] Shi, G.; Shao, C.; Pan, S.; Yu, J.; Zhang, Y. Org. Lett. 2015, 17, 38.
[28] Zhao, W.-M.; Chen, X. L.; Yuan, J. W.; Qu, L. B.; Duan, L. K.; Zhao, Y. F. Chem. Commun. 2014, 50, 2018.
[29] Wang, J.; Li, S.; Yang, T.; Yang, J. Tetrahedron 2014, 70, 9029.
[30] Mai, W. P.; Sun, B.; You, L. Q.; Yang, L. R.; Mao, P.; Yuan, J. W.; Xiao, Y. M.; Qu, L. B. Org. Biomol. Chem. 2015, 13, 2750.
[31] Mahajan, P. S.; Mhaske, S. B. Org. Lett. 2018, 20, 2092.
[32] Xia, R.; Xie, M. S.; Niu, H. Y.; Qu, G. R.; Guo, H. M. Org. Lett. 2014, 16, 444.
[33] Cheng, K.; Zhao, B.; Qi, C. RSC Adv. 2014, 4, 48698.
[34] Chang, S.; Wang, J.; Dong, L.; Wang, D.; Feng, B.; Shi, Y. RSC Adv. 2017, 7, 51928.
[35] Zhang, N.; Yang, D.; Wei, W.; Yuan, L.; Nie, F.; Tian, L.; Wang, H. J. Org. Chem. 2015, 80, 3258.
[36] Wu, S.; Yu, H.; Hu, Q.; Yang, Q.; Xu, S.; Liu, T. S. Tetrahedron Lett. 2017, 58, 4763.
[37] Wang, H.; Guo, L. N.; Duan, X. H. Chem. Commun. 2014, 50, 7382.
[38] Meng, M.; Wang, G.; Yang, L.; Cheng, K.; Qi, C. Adv. Synth. Catal. 2018, 360, 1218.
[39] Zou, H.; Li, Y.; Yang, Y.; Li, J.; Xiang, J. Adv. Synth. Catal. 2018, 360, 1439.
[40] Suresh, R.; Kumaran, R. S.; Senthilkumar, V.; Muthusubramanian, S. RSC Adv. 2014, 4, 31685.
[41] Wang, H.; Zhou, S. L.; Guo, L. N.; Duan, X. H. Tetrahedron 2015, 71, 630.
[42] Zeng, X.; Liu, C.; Wang, X.; Zhang, J.; Wang, X.; Hu, Y. Org. Biomol. Chem. 2017, 15, 8929.
[43] Seo, S.; Slater, M.; Greaney, M. F. Org. Lett. 2012, 14, 2650.
[44] Seo, S.; Taylor, J. B.; Greaney, M. F. Chem. Commun. 2012, 48, 8270.
[45] Grainger, R.; Nikmal, A.; Cornella, J.; Larrosa, I. Org. Biomol. Chem. 2012, 10, 3172.
[46] Zhan, K.; Li, Y. Catalysts 2017, 7, 314.
[47] Kan, J.; Huang, S.; Lin, J.; Zhang, M.; Su, W. Angew. Chem., Int. Ed. 2015, 54, 2199.
[48] Yuan, J.; Yang, L.; Mao, P.; Qu, L. Org. Chem. Front. 2017, 4, 545.
[49] Luo, Y.; Pan, X.; Wu, J. Tetrahedron Lett. 2010, 51, 6646.
[50] Bhadra, S.; Dzik, W. I.; Goossen, L. J. J. Am. Chem. Soc. 2012, 134, 9938.
[51] Li, M.; Petersen, J. L.; Hoover, J. M. Org. Lett. 2017, 19, 638.
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