N-Heterocyclic Carbene Catalyzed and N-Fluorobenzenesulfonimide Mediated Oxidative Synthesis of Perester and Amide

doi:10.6023/cjoc201511013

Chin. J. Org. Chem. ›› 2016, Vol. 36 ›› Issue (1): 105-112.DOI: 10.6023/cjoc201511013 Previous Articles Next Articles

Articles

N-氟代双苯磺酰胺介导的氮杂卡宾氧化催化合成过氧酯及酰胺的研究

谢仰熹, 李方怿, 赵常贵, 汪舰

清华大学药学院北京 100084

收稿日期:2015-11-07 修回日期:2015-11-24 发布日期:2015-12-04
通讯作者: 汪舰 E-mail:wangjian2012@tsinghua.edu.cn
基金资助:
青年千人计划资助项目.

N-Heterocyclic Carbene Catalyzed and N-Fluorobenzenesulfonimide Mediated Oxidative Synthesis of Perester and Amide

Xie Yangxi, Li Fangyi, Zhao Changgui, Wang Jian

School of Pharmaceutical Sciences, Tsinghua University, Beijing 100084

Received:2015-11-07 Revised:2015-11-24 Published:2015-12-04
Supported by:
Project supported by the “Thousand Plan” Youth Program of China.

Cite this article

Xie Yangxi, Li Fangyi, Zhao Changgui, Wang Jian. N-Heterocyclic Carbene Catalyzed and N-Fluorobenzenesulfonimide Mediated Oxidative Synthesis of Perester and Amide[J]. Chin. J. Org. Chem., 2016, 36(1): 105-112.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

share this article

References

[1] (a) Enders, D.; Niemeier, O.; Henseler, A. Chem. Rev. 2007, 107, 5606.(b) Grossmann, A.; Enders, D. Angew. Chem., Int. Ed. 2012, 51, 314.(c) Bugaut, X.; Glorius, F. Chem. Soc. Rev. 2012, 41, 3511.(d) Izquierdo, J.; Hutson, G. E.; Cohen, D. T.; Scheidt, K. A. Angew. Chem., Int. Ed. 2012, 51, 11686.(e) Ryan, S. J.; Candish, L.; Lupton, D. W. Chem. Soc. Rev. 2013, 42, 4906.(f) DeSarkar, S.; Biswap, A.; Samanta, R. C.; Studer, A. Chem. Eur. J. 2013, 19, 4664.(g) Chauhan, P.; Enders, D. Angew. Chem., Int. Ed. 2014, 53, 1485.(h) Hopkinson, M. N.; Richter, C.; Schedler, M.; Glorius, F. Nature 2014, 510, 485.(i) Flanigan, D. M.; Romanov-Michailidis, F.; White, N. A.; Rovis, T. Chem. Rev.2015, 115, 9307.(j) Chai, H. X.; Li, J. R.; Ynag, L. P.; Liu, M. X.; Yang, D. L.; Shi, D. X. Chin. J. Chem. 2014, 32, 865.(k) Shen, L. T.; Jia, W. Q.; Ye, S. Chin. J. Chem. 2014, 32, 814.(l) He, L.; Cai, Z. H.; Ma, X. W.; Du, G. F. Chin. J. Chem.2013, 31,1573.(m) Qu, M. N.; He, J. M. Chin. J. Org. Chem.2011, 31,1388.(n) He, L.; Cai, Z. H.; Ma, X. W.; Du, G. F. Chin. J. Chem. 2013, 31, 1573.
[2] (a) Ryan, S. J.; Candish, L.; Lupton, D. W. J. Am. Chem. Soc. 2009, 131, 14176.(b) Hao, L.; Du, Y.; Lv, H.; Chen, X. K.; Jiang, H. S.; Shao, Y. L.; Chi, Y. R. Org. Lett. 2012, 14, 2154.(c) Cheng, J.; Huang, Z.; Chi, Y. R. Angew. Chem., Int. Ed. 2013, 52, 8592.(d) Lee, A.; Younai, Y.; Price, C. K.; Izquierdo, J.; Mishra, R. K.; Scheidt, K. A. J. Am. Chem. Soc. 2014, 136,10589.(e) Chen, X. Y.; Gao, Z. H.; Song, C. Y.; Zhang, C. L.; Wang, Z. X.; Ye, S. Angew. Chem., Int. Ed. 2014, 53, 11611.(f) Chan, A.; Scheidt, K. A. Org. Lett. 2005, 7, 905.(g) Zeitler, K. Org. Lett. 2006, 8, 637.(h) Reynolds, N. T.; Alaniz, J. R.; Rovis, T. J. Am. Chem. Soc. 2004, 126, 9518.(i) Sun, F. G.; Sun, L. H.; Ye, S. Adv. Synth. Catal. 2011, 353, 3134.(j) Yetra, S. R.; Bhunia, A.; Patra, A.; Mane, M. V.; Vanka, K.; Biju, A. T. Adv. Synth. Catal. 2013, 355, 1089.(k) Yetra, S. R.; Kaicharla, T.; Kunte, S. S.; Gonnade, R. G.; Biju, A. T. Org. Lett. 2013, 15, 5202.(l) Yao, C.; Wang, D.; Lu, J.; Li, T.; Jiao, W.; Yu, C. Chem. Eur. J. 2012, 18, 1914.(m) Maki, B. E.; Chan, A.; Phillips, E. M.; Scheidt, K. A. Org. Lett. 2007, 9, 371.(n) Maki, B. E.; Chan, A.; Scheidt, K. A. Synthesis 2008, 1306.(o) Kaeobamrung, J.; Mahatthananchai, J.; Zheng, P.; Bode, J. W. J. Am. Chem. Soc. 2010, 132, 8810.(p) Mahatthananchai, J.; Zheng, P.; Bode, J. W. Angew. Chem., Int. Ed. 2011, 50, 1673.(q) Mahatthananchai, J.; Kaeobamrung, J.; Bode, J. W. ACS Catal. 2012, 2, 494.(r) Zhu, Z. Q.; Zheng, X. L.; Jiang, N. F.; Wan, X.; Xiao, J. C. Chem. Commun. 2011, 47, 8670.(s) Zhu, Z. Q.; Xiao, J. C. Adv. Synth. Catal. 2010, 352, 2455.(t) De Sarkar, S.; Studer, A. Angew. Chem., Int. Ed. 2010, 49, 9266.(u) Rong, Z. Q.; Jia, M. Q.; You, S. L. Org. Lett. 2011, 13, 4080.(v) Wanner, B.; Mahatthananchai, J.; Bode, J. W. Org. Lett. 2011, 13, 5378.(w) Kravina, A. G.; Mahatthananchai, J.; Bode, J. W. Angew. Chem., Int. Ed. 2012, 51, 9433.(x) De Sarkar, S.; Grimme, S.; Studer, A. J. Am. Chem. Soc. 2010, 132, 1190.(y) Maji, B.; Vedachalan, S.; Ge, X.; Cai, S.; Liu, X. W. J. Org. Chem. 2011, 76, 3016.(z) Corey, E. J.; Katzenellenbogen, J. A.; Gilman, N. W.; Roman, S. A.; Erickson, B. W. J. Am. Chem. Soc. 1968, 90, 5618.
[3] (a) Wu, Z. J.; Li, F. Y.; Wang, J. Angew. Chem., Int. Ed. 2015, 54, 1629.(b) Goodman, C. G.; Walker, M. M.; Johnson, J. S. J. Am. Chem. Soc. 2015, 137, 122.
[4] Li, F. Y.; Wu, Z. J.; Wang, J. Angew. Chem. Int. Ed. 2015, 54, 656.
[5] (a) Denisov, E. T.; Denisova, T. G.; Pokidova, T. S., Handbook of Free Radical Initiators, Wiley-Interscience, New Jersey, 2003.(b) Gupta, S. N.; Gupta, I.; Neckers, D. C. J. Polym. Sci., Polym. Chem. Ed. 1981, 19, 103.(c) Wang, L.; Liu, X.; Li, Y. Macromolecules 1998, 31, 3446.(d) Ando, W. Organic Peroxides, Wiley-Interscience, New York, 1992.
[6] (a) Montevecchi, P. C.; Manetto, A.; Navacchia, M. L.; Chatgilialoglu, C. Tetrahedron 2004, 60, 4303.(b) Antonello, S.; Crisma, M.; Formaggio, F.; Moretto, A.; Taddei, F.; Toniolo, C.; Maran, F. J. Am. Chem. Soc. 2002, 124, 11503.(c) Shah, B. K.; Neckers, D. C. J. Am. Chem. Soc. 2004, 126, 1830. (d) Andrus, M. B.; Zhou, Z. J. Am. Chem. Soc. 2002, 124, 8806.(e) Eames, J.; Watkinson, M. Angew. Chem., Int. Ed. 2001, 40, 3567.(f) Powell, D. A.; Fan, H. J. Org. Chem. 2010, 75, 2726;(g) Formaggio, F.; Crisma, M.; Scipionato, L.; Antonello, S.; Maran, F.; Toniolo, C. Org. Lett. 2004, 6, 2753.(h) Malkov, A. V.; Bella, M.; Langer, V.; Kocovsky, P. Org. Lett. 2000, 2, 3047.(i) Andrus, M. B.; Lashley, J. C. Tetrahedron 2002, 58, 845.(j) Kohmura, Y.; Katsuki, T. Tetrahedron Lett. 2000, 41, 3941.(k) Rispens, M. T.; Zondercu, C.; Feringa, B. L. Tetrahedron: Asymmetry 1995, 6, 661.
[7] De Sarkar, S.; Studer, A. Org. Lett. 2010, 12, 1992.
[8] Wei, W.; Zhang, C.; Xu, Y.; Wan, X. B. Chem. Commun. 2011, 47, 10827.
[9] (a) Achar, T. K.; Mal, P. J. Org. Chem. 2015, 80, 666.(b)Ren, W.; Yamane, M. J. Org. Chem. 2010, 75, 8410.(c) Ojeda-Porras, A.; Hernández-Santana, A.; Gamba-Sánchez, D. Green Chem. 2015, 17, 3157.(d) Pilo, M.; Porcheddu, A.; De Luca, L. Org. Biomol. Chem.2013, 11,8241.(e) Rushworth, P. J.; Hulcoop, D. G.; Fox, D. J. J. Org. Chem. 2013, 78, 9517.

N-氟代双苯磺酰胺介导的氮杂卡宾氧化催化合成过氧酯及酰胺的研究

N-Heterocyclic Carbene Catalyzed and N-Fluorobenzenesulfonimide Mediated Oxidative Synthesis of Perester and Amide

PDF

Knowledge

Abstract

Cite this article

share this article

References

Related Articles 8

Recommended Articles

Metrics

Comments

[1]	Wang Zhanlin, Li Ruyi, Qian Huimin, Yao Changsheng. Effect of Temperature on N-Heterocyclic Carbene-Catalyzed[3+3] Annulation of α-Bromoenal with Enaminone [J]. Chin. J. Org. Chem., 2019, 39(7): 2075-2083.
[2]	Li Sha, Yang Wenhan, Luo Xian, Yao Changsheng. An Efficient N-Heterocyclic Carbene (NHC)-Catalyzed Synthesis of Polysubstituted Cyclopentene [J]. Chin. J. Org. Chem., 2019, 39(5): 1404-1410.
[3]	Wang Tao, Xu Kai, Zhang An'an, Wang Wanli, Liu Lantao. Buchwald-Hartwig Amination of Aryl Chlorides Catalyzed by Trinuclear N-Heterocyclic Carbene-Palladium(Ⅱ) Complexes [J]. Chin. J. Org. Chem., 2018, 38(1): 259-265.
[4]	Wang Fan, Hu Yucai, Shen An, Cao Yucai. Novel Pd-N-Heterocyclic Carbene Complexes: Design, Synthesis and Applyment in Buchwald-Hartwig Cross Coupling Reaction [J]. Chin. J. Org. Chem., 2017, 37(8): 2050-2056.
[5]	Zhang Jie, Du Guangfen, Gu Chengzhi, Dai Bin. Strecker Reaction of Ethyl Cyanoformate with Aldimines Catalyzed by N-Heterocyclic Carbene [J]. Chin. J. Org. Chem., 2017, 37(4): 914-919.
[6]	Yang Liangru, Guo Qi, Xiao Yongmei, Mao Pu. Development of Chelating N-Heterocyclic Carbene Metal Complexes [J]. Chin. J. Org. Chem., 2015, 35(9): 1834-1847.
[7]	Jiang Xiaojun, Shen Yajing, Liu Zelong, Lü Xuliang, Tu Tao. Acenaphthoimidazole N-Heterocyclic Carbene Palladium ComplexesCatalyzed Cyanation Reactions in Aqueous Accelerated byMicrowave Irradiation [J]. Chin. J. Org. Chem., 2015, 35(11): 2389-2392.
[8]	Gao Yanxuan, Zhou Hongyong, Li Yunqing, Wang Jiaxi. Synthesis and Application of N-Heterocyclic Carbene in Transfer Hydrogenation [J]. Chin. J. Org. Chem., 2012, 32(08): 1493-1497.