Notes

Research on the Tandem Reaction via Chloropalladation/Heck Cross Coupling of o-(Alkynyl)styrenes with Pd/O2

  • Qiu Huihua ,
  • Cheng Borui ,
  • Huang Yingsi ,
  • Chen Cui ,
  • Zhou Peng
Expand
  • School of Chemical Engineering, Guangdong University of Petrochemical Technology, Maoming 525000

Received date: 2018-01-23

  Revised date: 2018-03-26

  Online published: 2018-04-12

Supported by

Project supported by the National Natural Science Foundation of China (No. 21602035) and the Natural Science Foundation of Guangdong Province (No. 2016A030307030).

Abstract

An economic and environmental synthestic method for 3-chloroindenes from o-(alkynyl)styrenes through tandem reactions including choropalladation/Heck cross coupling in Pd/O2 system was reported. Taking green dioxygen as sole oxidant and LiCl as chlorine source, 13 functionalized 3-chloroindenes could be synthesized in moderate to high yield without the addition of CuCl2

Cite this article

Qiu Huihua , Cheng Borui , Huang Yingsi , Chen Cui , Zhou Peng . Research on the Tandem Reaction via Chloropalladation/Heck Cross Coupling of o-(Alkynyl)styrenes with Pd/O2[J]. Chinese Journal of Organic Chemistry, 2018 , 38(7) : 1817 -1822 . DOI: 10.6023/cjoc201801030

References

[1] Selected review and examples on chloropalladation, please see:(a) Lu, X. In Handbook of Organopalladium Chemistry for Organic Synthesis, Ed.:Negishi, E., Wiley-Interscience, New York, 2002, Vol. 2, pp. 2267~2288.
(b) Huang, L.; Wang Q.; Liu, X.; Jiang, H. Angew. Chem., Int. Ed. 2012, 51, 5696.
(c) Huang, L.; Wang, Q.; Wu, W.; Jiang, H. J. Org. Chem. 2014, 79, 7734.
(d) Zhang, Z.; Ouyang, L.; Wu, W.; Li, J.; Zhang, Z.; Jiang, H. J. Org. Chem. 2014, 79, 10734.
(e) Sun, N.; Li, Y.; Yin, G.; Jiang, S. Eur. J. Org. Chem. 2013, 2541.
(f) Zhang, Z.; Wu, W.; Liao, J.; Li, J.; Jiang, H. Chem.-Eur. J. 2015, 21, 6708.
(g) Derosa, J.; Cantu, A. L.; Boulous, M. N.; O'Duill, M. L.; Turnbull, J. L.; Liu, Z.; Torre, D. L. T.; Engle, K. M. J. Am. Chem. Soc. 2017, 139, 5183.
(h) Li, J.; Hu, W.; Li, C. Yang, S.; Wu, W.; Jiang, H. Org. Chem. Front. 2017, 4, 373.
[2] Selected examples on chloropalladation with CuCl2:(a) Huang, J.; Dong, Y.; Wang, X.; Luo, H. Chem. Commun. 2010, 46, 1035.
(b) An, Y.; Li, J.; Zhang, Z.; Li, C.; Yang, S. Chin. J. Org. Chem. 2016, 36, 2136 (in Chinese).
(安艳妮, 李建晓, 张振明, 李春生, 杨少容, 有机化学, 2016, 36, 2136.)
(c) Li, J.; Li, C.; Yang, S.; Luo, W. Chin. J. Org. Chem. 2015, 35, 898 (in Chinese).
(李建晓, 李春生, 杨少容, 罗维, 有机化学, 2015, 35, 898.)
[3] Review on the reactions with O2:(a) Wu, W.; Jiang, H. Acc. Chem. Res. 2012, 45, 1736.
(b) Wu, W.; Jiang, H. Acc. Chem. Res. 2014, 47, 2483.
(c) 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.)
(d) 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.)
(e) Xu, J.; Song, Q. Chin. J. Org. Chem. 2016, 36, 1151 (in Chinese).
(许健, 宋秋玲, 有机化学, 2016, 36, 1151.)
[4] For some selected examples, please see:(a) Citta, A.; Folda, A.; Bindoli, A.; Pigeon, P.; Top, S.; Vessières, A.; Salmain, M.; Jaouen, G.; Rigobello, M. P. J. Med. Chem. 2014, 57, 8849.
(b) Tehfe, M.; Dumur, F.; Graff, B.; Gigmes, D.; Fouassier, J.; Lalevée, J. Macromolecules 2013, 46, 3332.
(c) Mróz, W.; Villafiorita-Monteleone, F.; Pasini, M.; Grisci, G.; Paolino, M.; Razzano, V.; Cappelli, A.; Botta, C. Mater. Lett. 2015, 142, 197.
(d) Guerlin, A.; Dumur, F.; Dumas, E.; Miomandre, F.; Wantz, G. C.; Mayer, R. Org. Lett. 2010, 12, 2382.
[5] Selected examples, please see:(a) Mosslemin, M. H.; Shams, N.; Esteghamat, H.; Anaraki-Ardakani, H. Chin. Chem. Lett. 2013, 24, 1095.
(b) Zhou, F.; Yang, M.; Lu, X. Org. Lett. 2009, 11, 1405.
(c) Bu, X.; Hong, J.; Zhou, X. Adv. Synth. Catal. 2011, 353, 2111.
(d) Jia, X.; Petrone, D. A.; Lautens, M. Angew. Chem., Int. Ed. 2012, 51, 9870.
(e) Zeng, Z.; Ilies, L.; Nakamura, E. J. Am. Chem. Soc. 2011, 133, 17638.
(f) Huang, X.; Yang, X.; Song, R.; Li, J. J. Org. Chem. 2014, 79, 1025.
[6] Ye, S.; Gao, K.; Zhou, H.; Yang X.; Wu, J. Chem. Commun. 2009, 5406.
[7] Zhou, P.; Liu, W.; Qiu, H. Chem. Lett. 2015, 44, 1637.
[8] (a) Shi, Z.; Zhang, C.; Li, S.; Pan, D. Ding, S.; Cui, Y.; Jiao, N. Angew. Chem., Int. Ed. 2009, 48, 4572.
(b) Lafrance, M.; Fagnou, K. J. Am. Chem. Soc. 2006, 128, 16496.
[9] Zhou, F.; Han, X.; Lu, X. J. Org. Chem. 2011, 76, 1491.

Outlines

/