研究论文

不使用银氧化剂的噻唑/噁唑钯催化二聚反应(英文)

  • 李瑶 ,
  • 马丽芳 ,
  • 王晓姣 ,
  • 雷搏文 ,
  • 赵怡 ,
  • 杨嘉宇 ,
  • 李子元
展开
  • 四川大学化学工程学院 制药与生物工程系 成都 610065

收稿日期: 2016-12-20

  修回日期: 2017-03-09

  网络出版日期: 2017-03-14

基金资助

中央高校基本科研业务费(No.2016SCU11020)资助项目.

Palladium(II)-Catalyzed Homocoupling of Oxazole/Thiazole in Absence of Silver Oxidant

  • Li Yao ,
  • Ma Lifang ,
  • Wang Xiaojiao ,
  • Lei Bowen ,
  • Zhao Yi ,
  • Yang Jiayu ,
  • Li Ziyuan
Expand
  • Department of Pharmaceutical and Biological Engineering, School of Chemical Engineering, Sichuan University, Chengdu 610065

Received date: 2016-12-20

  Revised date: 2017-03-09

  Online published: 2017-03-14

Supported by

Project supported by the Fundamental Research Funds for the Central Universities (No. 2016SCU11020).

摘要

以Oxone作为氧化剂,实现了基于钯催化C-H键活化的噻唑/噁唑二聚反应,具有中等至优异的收率和理想的官能团耐受性,且无需添加其它添加剂或配体.与本作者过去报道的二聚反应相比,本反应避免使用化学当量的银盐作为氧化剂,使得本反应更具经济性和环境友好性.此外,初步提出了一条涉及二价钯/四价钯催化循环的反应机理.进一步将该环境友好的氧化剂应用于其他类型的偶联反应,以及将其应用于含有噻唑/噁唑结构的天然产物结构修饰上,尚在进行中.

本文引用格式

李瑶 , 马丽芳 , 王晓姣 , 雷搏文 , 赵怡 , 杨嘉宇 , 李子元 . 不使用银氧化剂的噻唑/噁唑钯催化二聚反应(英文)[J]. 有机化学, 2017 , 37(5) : 1213 -1219 . DOI: 10.6023/cjoc201612052

Abstract

Homocoupling of oxazole/thiazole via palladium-catalyzed C-H bond activation using oxone as an oxidant has been achieved in moderate to excellent yields with good functional group tolerance. No other additive or ligand was employed in this efficient reaction. Comparing to our previously reported homocoupling of oxazole/thiazole, the absence of stoichiometric silver oxidant renders this reaction more environment-benign and cost-effective. A preliminary mechanism involving a Pd/Pd catalytic cycle is also proposed. Further exploration of this environmental-benign oxidant on other categories of coupling reactions, as well as applications of this revised homocoupling to structural modification of oxazole/thiazole-containing natural products, are undergoing in our lab.

参考文献

[1] (a) Taori, K.; Paul, V. J.; Luesch, H. J. Am. Chem. Soc. 2008, 130, 1806.
(b) Wright, A. E.; Botelho, J. C.; Guzman, E.; Harmody, D.; Linley, P.; McCarthy, P. J.; Pitts, T. P.; Pomponi, S. A.; Reed, J. K. J. Nat. Prod. 2007, 70, 412.
(c) Hofle, G.; Bedorf, N.; Steinmetz, H.; Schomburg, D.; Gerth, K.; Reichenbach, H. Angew. Chem., Int. Ed. 1996, 35, 1567.
(d) Oku, N.; Takada, K.; Fuller, R. W.; Wilson, J. A.; Peach, M. L.; Pannell, L. K.; McMahon, J. B.; Gustafson, K. R. J. Am. Chem. Soc. 2010, 132, 10278.
[2] (a) Li, Y.-M.; Milne, J. C.; Madison, L. L.; Kolter, R.; Walsh, C. T. Science 1996, 274, 1188.
(b) Walsh, C. T. Science 2004, 303, 1805.
[3] (a) Liu, C.; Yuan, J.; Gao, M.; Tang, S.; Li, W.; Shi, R.; Lei, A. Chem. Rev. 2015, 115, 12138.
(b) Yang, L.; Huang, H. Chem. Rev. 2015, 115, 3468.
(c) Cheng, C.; Hartwig, J. F. Chem. Rev. 2015, 115, 8946.
(d) Ackermann, L. Chem. Rev. 2011, 111, 1315.
(e) Sun, C.-L.; Li, B.-J.; Shi, Z.-J. Chem. Rev. 2011, 111, 1293.
(f) Lyons, T. W.; Sanford, M. S. Chem. Rev. 2010, 110, 1147.
(g) Denise, A. C.; Bergman, R. G.; Ellman, J. A. Chem. Rev. 2010, 110, 624.
(h) Chen, X.; Engle, K. M.; Wang, D.-H.; Yu, J.-Q. Angew. Chem., Int. Ed. 2009, 48, 5094.
(i) Wang, L.; Li, Z.; Wan, K.; Qu, X.; Hu, S.; Wang, F. Chin. J. Org. Chem. 2016, 36, 889 (in Chinese). (王亮, 李站, 万康, 瞿星, 胡思前, 王锋, 有机化学, 2016, 36, 889.)
(j) He, J.; Lou, S.; Xu, D. Chin. J. Org. Chem. 2016, 36, 1218 (in Chinese). (何将旗, 娄绍杰, 许丹倩, 有机化学, 2016, 36, 1218.)
(k) 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.)
(l) 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.)
(m) Gang, F.; Xu, G.; Dong, T.; Yang, L.; Du, Z. Chin. J. Org. Chem. 2015, 35, 1428 (in Chinese). (刚芳莉, 徐光利, 董涛生, 杨丽, 杜正银, 有机化学, 2015, 35, 1428.)
(n) Tang, M.; Huo, X.; Meng, Q.; Zhang, W. 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.)
(o) Yu, J.; Ding, K. Acta Chim. Sinica 2015, 73, 1223 (in Chinese). (余金权, 丁奎岭, 化学学报, 2015, 73, 1223.)
(p) Zhou, L.; Lu, W. Acta Chim. Sinica 2015, 73, 1250 (in Chinese). (周励宏, 陆文军, 化学学报, 2015, 73, 1250.)
(q) Shang, X.; Liu, Z. Acta Chim. Sinica 2015, 73, 1275 (in Chinese). (尚筱洁, 柳忠全, 化学学报, 2015, 73, 1275.)
(r) Liao, G.; Shi, B. Acta Chim. Sinica 2015, 73, 1283 (in Chinese). (廖港, 史炳锋, 化学学报, 2015, 73, 1283.)
[4] (a) Harari, M.; Couly, F.; Fruit, C.; Besson, T. Org. Lett. 2016, 18, 3282.
(b) Gu, J.; Cai, C. RSC Adv. 2015, 5, 56311.
(c) Bon, J. L.; Feng, D.; Marder, S. R.; Blakey, S. B. J. Org. Chem. 2014, 79, 7766.
(d) Ferguson, D. M.; Rudolph, S. R.; Kalyani, D. ACS Catal. 2014, 4, 2395.
(e) Chen, X.; Huang, X.; He, Q.; Xie, Y.; Yang, C. Chem. Commun. 2014, 50, 3996.
(f) Liu, W.; Yu, X.; Kuang, C. Org. Lett. 2014, 16, 1798.
(g) Fu, X.-P.; Xuan, Q.-Q.; Liu, L.; Wang, D.; Chen, Y.-J.; Li, C.-J. Tetrahedron 2013, 69, 4436.
(h) Dong, J.; Huang, Y.; Qin, X.; Cheng, Y.; Hao, J.; Wan, D.; Li, W.; Liu, X.; You, J. Chem. Eur. J. 2012, 18, 6158.
(i) Wu, G.; Zhou, J.; Zhang, M.; Hu, P.; Su, W. Chem. Commun. 2012, 48, 8964.
[5] (a) Lohrey, L.; Uehara, T. N.; Tani, S.; Yamaguchi, J.; Humpf, H.-U.; Itami, K. Eur. J. Org. Chem. 2014, 3387.
(b) Sekizawa, H.; Amaike, K.; Itoh, Y.; Suzuki, T.; Itami, K.; Yamaguchi, J. ACS Med. Chem. Lett. 2014, 5, 582.
(c) Tani, S.; Uehara, T. N.; Yamaguchi, J.; Itami, K. Chem. Sci. 2014, 5, 123.
(d) Shibahara, F.; Yamauchi, T.; Yamaguchi, E.; Murai, T. J. Org. Chem. 2012, 77, 8815.
(e) Kirchberg, S.; Tani, S.; Ueda, K.; Yamaguchi, J.; Studer, A.; Itami, K. Angew. Chem., Int. Ed. 2011, 50, 2387.
[6] (a) Heiskanen, J. P.; Vivo, P.; Saari, N. M.; Hukka, T. I.; Kastinen, T.; Kaunisto, K.; Lemmetyinen, H. J.; Hormi, O. E. O. J. Org. Chem. 2016, 81, 1535.
(b) Gao, S.; Yang, C.; Huang, Y.; Zhao, L.; Wu, X.; Yao, H.; Lin, A. Org. Biomol. Chem. 2016, 14, 840.
(c) Liu, X.-W.; Shi, J.-L.; Wei, J.-B.; Yang, C.; Yan, J.-X.; Peng, K.; Dai, L.; Li, C.-G.; Wang, B.-Q.; Shi, Z.-J. Chem. Commun. 2015, 51, 4599.
(d) Zhou, H.; Gai, K.; Lin, A.; Xu, J.; Wu, X.; Yao, H. Org. Biomol. Chem. 2015, 13, 1243.
(e) Chen, X.; Huang, X.; He, Q.; Xie, Y.; Yang, C. Chem. Commun. 2014, 50, 3996.
(f) Liu, B.; Huang, Y.; Lan, J.; Song, F.; You, J. Chem. Sci. 2013, 4, 2163.
(g) Chen, L.; Bruneau, C.; Dixneuf, P. H.; Doucet, H. ChemCatChem 2013, 5, 1956.
(h) Yan, T.; Chen, L.; Bruneau, C.; Dixneuf, P. H.; Doucet, H. J. Org. Chem. 2013, 78, 4177.
[7] (a) Li, Z.; Ma, L.; Xu, J.; Kong, L.; Wu, X.; Yao, H. Chem. Commun. 2012, 48, 3763.
(b) Li, Z.; Zhou, H.; Xu, J.; Wu, X., Yao, H. Tetrahedron 2013, 69, 3281.
(c) Li, Z.; Ma, L.; Tang, C.; Xu, J.; Wu, X.; Yao, H. Tetrahedron Lett. 2011, 52, 5643.
(d) Li, Z.; Wang, Y.; Huang, Y.; Tang, C.; Xu, J.; Wu, X.; Yao, H. Tetrahedron 2011, 67, 5550.
[8] (a) Liang, Y.-F.; Wang, X.; Yuan, Y.; Liang, Y.; Li, X.; Jiao, N. ACS Catal. 2015, 5, 6148.
(b) Desai, L. V.; Malik, H. A.; Sanford, M. S. Org. Lett. 2006, 8, 1141.
(c) Hussain, H.; Green, I. R.; Ahmed, I. Chem. Rev. 2013, 113, 3329.
[9] (a) Perez, L. J.; Faulkner, D. J. J. Nat. Prod. 2003, 66, 247.
(b) Foster, M. P.; Concepcion, G. P.; Garaan, G. B.; Ireland, C. M. J. Org. Chem. 1992, 57, 6671.
[10] (a) Huang, Y.; Gan, H.; Li, S.; Xu, J.; Wu, X.; Yao, H. Tetrahedron Lett. 2010, 51, 1751.
(b) Huang, Y.; Ni, L.; Gan, H.; He, Y.; Xu, J.; Wu, X.; Yao, H. Tetrahedron 2011, 67, 2066.
(c) Wang, Y.; Li, Z.; Huang, Y.; Tang, C.; Wu, X.; Xu, J.; Yao, H. Tetrahedron 2011, 67, 7406.

文章导航

/