研究论文

氧气作为唯一氧化剂的钯催化咖啡因或尿嘧啶C-H键直接芳基化反应

  • 潘帼帅 ,
  • 吴孔川 ,
  • 邓泽颖 ,
  • 张馨予 ,
  • 张晓凤 ,
  • 林深 ,
  • 黄秋锋
展开
  • a 福建师范大学化学与材料学院 福州 350007;
    b 福建省高分子材料重点实验室 福州 350007

收稿日期: 2018-02-04

  修回日期: 2018-03-25

  网络出版日期: 2018-04-13

基金资助

国家自然科学基金(No.6152010615)、福建省自然科学基金(No.2017J01572)、福建省教育厅青年重点基金(No.JZ160424)和福建省高校新世纪人才基金和福建师范大学省级大学生创新训练计划(No.201710394061)资助项目.

Palladium-Catalyzed C-H Direct Arylation of Uracils and Caffeines with Arenes Using Molecular Oxygen as the Sole Oxidant

  • Pan Guoshuai ,
  • Wu Kongchuan ,
  • Deng Zeying ,
  • Zhang Xinyu ,
  • Zhang Xiaofeng ,
  • Lin Shen ,
  • Huang Qiufeng
Expand
  • a College of Chemistry & Materials Science, Fujian Normal University, Fuzhou 350007;
    b Key Laboratory of Polymer Materials of Fujian Province, Fuzhou 350007

Received date: 2018-02-04

  Revised date: 2018-03-25

  Online published: 2018-04-13

Supported by

Project supported by the National Natural Science Foundation of China (No. 6152010615), the Natural Science Foundation of Fujian Province (No. 2017J01572), the Foundation of Fujian Educational Committee (No. JZ160424), the Fujian Province University Fund for New Century Excellent Talents, and Undergraduate Training Program for Innovation and Entrepreneurship (No. 201710394061).

摘要

报道了钯催化咖啡因或尿嘧啶C-H与芳烃C-H的脱氢偶联反应.反应最大特点是采用常压氧气作为唯一氧化剂.反应对很多官能团,比如卤素、酯基、硝基、腈基、醚等,都有很好的容忍度.本方法为制备C6-芳基尿嘧啶或C8-芳基咖啡因衍生物提供了简便、直接和绿色经济路线.

本文引用格式

潘帼帅 , 吴孔川 , 邓泽颖 , 张馨予 , 张晓凤 , 林深 , 黄秋锋 . 氧气作为唯一氧化剂的钯催化咖啡因或尿嘧啶C-H键直接芳基化反应[J]. 有机化学, 2018 , 38(8) : 2076 -2084 . DOI: 10.6023/cjoc201802008

Abstract

Palladium-catalyzed cross-dehydrogenative coupling of uracil or caffeine with unactivated arenes has been developed. The approach was characterized by using atmospheric pressure of molecular oxygen as the sole oxidant. Functional groups such as halo, ester, nitro, nitrile and ether are well-tolerated under the reaction conditions. This novel strategy provides a straightforward, facile and economical route to C6-aryl uracil derivatives or C8-aryl caffeine derivatives.

参考文献

[1] (a) Roudesly, F.; Oble, J.; Poli, G. J. Mol. Catal. A:Chem. 2017, 426, 275.
(b) Wu, Y.; Wang, J.; Mao, F.; Kwong, F. Y. Chem. Asian J. 2014, 9, 26.
(c) Girard, S. A.; Knauber, T.; Li, C.-J. Angew. Chem., Int. Ed. 2014, 53, 74.
(d) Yang, Y.; Lan, J.; You, J. Chem. Rev. 2017, 117, 8787.
(e) Zhang, M.; Zhang, Y.; Jie, X.; Zhao, H.; Li, G.; Su, W. Org. Chem. Front. 2014, 1, 843.
(f) Gensch, T.; Hopkinson, M. N.; Glorius, F.; Wencel-Delord, J. Chem. Soc. Rev. 2016, 45, 2900.
(g) Liu, C.; Yuan, J.; Gao, M.; Tang, S.; Li, W.; Shi, R.; Lei, A. Chem. Rev. 2015, 115, 12138.
(h) Chen, Z.; Wang, B.; Zhang, J.; Yu, W.; Liu, Z.; Zhang, Y. Org. Chem. Front. 2015, 2, 1107.
(i) Hu, W.; Long, Y. Chin. J. Org. Chem. 2017, 37, 2850(in Chinese). (胡玮, 龙亚秋, 有机化学, 2017, 37, 2850.)
[2] (a) Reddy, M. C.; Jeganmohan, M. Chem. Commun. 2015, 51, 10738.
(b) Gao, G.-L.; Xia, W.; Jain, P.; Yu, J.-Q. Org. Lett. 2016, 18, 744.
(c) Gong, H.; Zeng, H.; Zhou, F.; Li, C.-J. Angew. Chem., Int. Ed. 2015, 54, 5718.
(d) Yang, Z.; Qiu, F.-C.; Gao, J. Li, Z.-W.; Guan, B.-T. Org. Lett. 2015, 17, 4316.
(e) Lou, S.-J.; Mao, Y.-J.; Xu, D.-Q.; He, J.-Q.; Chen, Q.; Xu, Z.-Y. ACS Catal. 2016, 6, 3890.
(f) Huang, Y.; Wu, D.; Huang, J.; Guo, Q.; Li, J.; You, J. Angew. Chem., Int. Ed. 2004, 53, 12158.
(g) Qin, D.; Wang, J.; Qin, X.; Wang, C.; Gao, G.; You, J. Chem. Commun. 2015, 51, 6190.
(h) Zhang, X.-S.; Zhang, Y.-F.; Li, Z.-W.; Luo, F.-X.; Shi, Z.-J. Angew. Chem., Int. Ed. 2015, 54, 5478.
(i) Zhang, Y.; Zhao, H.; Zhang, M.; Su, W. Angew. Chem., Int. Ed. 2015, 54, 3817.
[3] (a) Li, B.; Lan, J.; Wu, D.; You, J. Angew. Chem., Int. Ed. 2015, 54, 14008.
(b) Gao, D.-W.; Gu, Q.; You, S.-L. J. Am. Chem. Soc. 2016, 138, 2544.
(c) Engle, K. M.; Wang, D.-H.; Yu, J.-Q. J. Am. Chem. Soc. 2010, 132, 14137.
(d) Wang, D.-H.; Engle, K. M.; Shi, B.-F.; Yu, J.-Q. Science 2010, 327, 315.
(e) Ye. X.; Shi, X. Org. Lett. 2014, 16, 4448.
(f) Huang, Q.; Ke, S.; Qiu, L.; Zhang, X.; Lin, S. ChemCatChem 2014, 6, 1531.
(g) Huang, Q.; Song, Q.; Cai, J.; Zhang, X.; Lin, S. Adv. Synth. Catal. 2013, 355, 1512.
[4] (a) Wu, K.; Song, C.; Cui, D. Chin. J. Org. Chem. 2017, 37, 586(in Chinese). (吴空, 宋婵, 崔冬梅, 有机化学, 2017, 37, 586.)
(b) Cheng, X.; Hu, X.; Lu, Z. Chin. J. Org. Chem. 2017, 37, 251(in Chinese). (程骁恺, 胡新根, 陆展, 有机化学, 2017, 37, 251.)
(c) Xu, J.; Song, Q. Chin. J. Org. Chem. 2016, 36, 1151(in Chinese). (许键, 宋秋玲, 有机化学, 2016, 36, 1151.)
(d) Pintér, Á.; Klussmann, M. Adv. Synth. Catal. 2012, 354, 701.
[5] (a) Zhang, Y.-H.; Shi, B.-F.; Yu, J.-Q. J. Am. Chem. Soc. 2009, 131, 5072.
(b) BraSche, G.; García-Fortanet, J.; Buchwald, S. L. Org. Lett. 2008, 10, 2207.
(c) Yang, D.; Mao, S.; Gao, Y.-R.; Guo, D.-D.; Guo, S.-H.; Lin B.; Wang, Y.-Q. RSC Adv. 2015, 2, 3727.
(d) Kim, N.; Min, M.; Hong, S. Org. Chem. Front. 2015, 2, 1621.
(e) Engle, K. M.; Wang, D.-H.; Yu, J.-Q. Angew. Chem., Int. Ed. 2010, 49, 6169.
(f) Liu, B.; Jiang, H.-Z.; Shi, B.-F. J. Org. Chem. 2014, 79, 1521.
(g) Lu, Y.; Wang, H.-W.; Spangler, J. E.; Chen, K.; Cui, P.-P.; Zhao, Y.; Sun, W.-Y.; Yu, J.-Q. Chem. Sci. 2015, 6, 1923.
[6] Huang, Q.; Zhang, X.; Qiu, L.; Wu, J.; Xiao, H.; Zhang, X.; Lin, S. Adv. Synth. Catal. 2015, 357, 3753.
[7] Zhang, X.; Su, L.; Qiu, L.; Fan, Z.; Zhang, X.; Lin, S.; Huang, Q. Org. Biomol. Chem. 2017, 15, 3499.
[8] (a) He, L.; Pei, H.; Ma, L.; Pu, Y.; Chen, J.; Liu, Z.; Ran, Y.; Lei, L.; Fu, S.; Tang, M.; Peng, A.; Long, C.; Chen, L. Eur. J. Med. Chem. 2014, 87, 595.
(b) Thomas, R.; Lee, J.; Chevalier, V.; Sadler, S.; Selesniemi, K.; Hatfield, S.; Sitkovsky, M.; Ondrechen, M. J.; Jones, G. B. Bioorg. Med. Chem. 2013, 21, 7453.
(c) Kim, S.-M.; Lee, M.; Lee, S. Y.; Park, E.; Lee, S.-M.; Kim, E. J.; Han, M. Y.; Yoo, T.; Ann, J.; Yoon, S.; Lee, J.; Lee, J. J. Med. Chem. 2016, 59, 9150.
(d) Qian, H.-Y.; Wang, Z.-L.; Pan, Y.-L.; Chen, L.-L.; Xie, X.; Chen, J.-Z. ACS Med. Chem. Lett. 2017, 8, 678.
(e) Rivara, S.; Piersanti, G.; Bartoccini, F.; Diamantini, G.; Pala, D.; Riccioni, T.; Stasi, M. A.; Cabri, W.; Borsini, F.; Mor, M.; Tarzia, G.; Minetti, P. J. Med. Chem. 2013, 56, 1247.
[9] Malakar, C. C.; Schmidt, D.; Conrad, J.; Beifuss, U. Org. Lett. 2011, 13, 1378.
[10] Kim, K. H.; Lee, H. S.; Kim, J. N. Tetrahedron Lett. 2011, 52, 6228.
[11] (a) Musaev, D. G.; Figg, T. M.; Kaledin, A. L. Chem. Soc. Rev. 2014, 43, 5009.
(b) Haines, B. E.; Musaev, D. G. ACS Catal. 2015, 5, 830.
(c) Li, G.; Leow, D.; Wan, L.; Yu, J.-Q. Angew. Chem., Int. Ed. 2013, 52, 1245.
(d) Musaev, D. G.; Kaledinm, A. L.; Shi, B.-F.; Yu, J.-Q. J. Am. Chem. Soc. 2012, 134, 1690.
(e) Wang, H.-L.; Hu, R.-B.; Zhang, H.; Zhou, A.-X.; Yang, S.-D. Org. Lett. 2013, 15, 5302.
(f) Cong, X.; Tang, H.; Wu, C.; Zhang, X. Organometallics 2013, 32, 6565.
(g) Cheng, G.-J.; Yang, Y.-F.; Liu, P.; Chen, P.; Sun, T.-Y.; Li, G.; Zhang, X.; Houk, K. N.; Yu, J.-Q.; Wu, Y.-D. J. Am. Chem. Soc., 2014, 136, 894.

文章导航

/