Citation: Zhou Peng, Qiu Huihua, Shi Jicheng. Palladium Catalyzed Cascade Cyclization of ortho-Alkenyl Bromobenzenes and Internal Alkynes for Multisubstituted Indenes[J]. Chinese Journal of Organic Chemistry, ;2016, 36(2): 425-431. doi: 10.6023/cjoc201508025 shu

Palladium Catalyzed Cascade Cyclization of ortho-Alkenyl Bromobenzenes and Internal Alkynes for Multisubstituted Indenes

1.
School of Chemical Engineering, Guangdong University of Petrochemical Technology, Maoming 525000

Corresponding author: Zhou Peng, zzd83@aliyun.com
Received Date: 25 August 2015
Revised Date: 12 October 2015

Fund Project: the Natural Science Foundation of Guangdong Province S2013040014944the National Natural Science Foundation of China 21272037

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This paper developed a new method for the construction of polysubstituted indenes. And a number of multisubstituted indenes have been synthesized from functional o-alkenyl bromobenzenes and alkynes in good yields through palladium-catalyzed annulations in N, N-dimethylformamide (DMF) taking Na₂CO₃as base. The methodology tolerates a variety of functional groups with simple reaction conditions and the catalyst can be reused.
- Pd-catalyzed,
- alkyne,
- o-alkenyl bromobenzene,
- indene,
- cascade reaction
1. [1]
  Some selected examples, please see: (a) Alcalde, E.; Mesquida, N.; López-Pérez, S.; Frigola, J.; Mercè R. J. Med. Chem. 2009, 52, 675.
  (b) 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.
  (c) Xie, J.; Zhou, Q. Acta Chim. Sinica 2014, 72, 778 (in Chinese).
  (谢建华, 周其林, 化学学报, 2014, 72, 778.)
2. [2]
  Some selected examples, please see: (a) Liu, L.; Fan, Y.; He, Q.; Zhang, Y.; Zhang-Negrerie, D.; Huang, J.; Du, Y.; Zhao, K. J. Org. Chem. 2012, 77, 3997.
  (b) Mróz, W.; Villafiorita-Monteleone, F.; Pasini, M.; Grisci, G.; Paolino, M.; Razzano, V.; Cappelli, A.; Botta, C. Mater. Lett. 2015, 142, 197.
  (c) Tehfe, M.; Dumur, F.; Graff, B.; Gigmes, D.; Fouassier, J.; Lalevée, J. Macromolecules 2013, 46, 3332.
3. [3]
  Some selected examples, please see: (a) Rao, Y.; Liu, M.; Yin, G. Chin. J. Org. Chem. 2015, 35, 719 (in Chinese).
  (饶寅, 刘美林, 殷国栋, 有机化学, 2015, 35, 719.)
  (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) Huang, X.; Yang, X.; Song, R.; Li, J. J. Org. Chem. 2014, 79, 1025.
  (e) Li, G.; Hu, H.; Kan, Y.; Ma, K. Chin. J. Org. Chem. 2014, 34, 903 (in Chinese).
  (李国栋, 胡华友, 阚玉和, 马奎蓉, 有机化学, 2015, 34, 903.)
  (f) Tan, F.; Chen, J.; Wang, P.; Xiao, W. Acta Chim. Sinica 2014, 72, 836 (in Chinese).
  (谭芬, 陈加荣, 王萍, 肖文精, 化学学报, 2014, 72, 836.)
4. [4]
  Some selected examples, please see: (a) Zhu, L.; Du, G.; Yang, W.; Min, L.; Liu, X.; Huang, S.; Han, Y.; Lee, C.-S. Chin. J. Org. Chem. 2013, 33, 2031 (in Chinese).
  (朱礼志, 杜广延, 杨炜, 闵龙, 刘小卒, 黄双平, 韩叶俭, 李志成, 有机化学, 2013, 33, 2031.)
  (b) Hu, L.; Gao, L.; Wan, C.; Wang, Z. Acta Chim. Sinica 2013, 71, 1603 (in Chinese).
  (胡露丹, 高令峰, 万常峰, 汪志勇, 化学学报, 2013, 71, 1603.)
  (c) Li, Y.; Wang, J.; Wei, X.; Yang, S. Chin. J. Org. Chem. 2015, 35, 638 (in Chinese).
  (李永红, 王君姣, 魏小红, 杨尚东, 有机化学, 2015, 35, 638.)
  (d) 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.)
5. [5]
  Selected reviews on Pd-catalyzed annulation of functional aryl halides: (a) Zeni, G.; Larock, R. C. Chem. Rev. 2006, 106, 4644.
  (b) Zeni, G.; Larock, R. C. Chem. Rev. 2004, 104, 2285.
6. [6]
  Shibata, K.; Satoh, T.; Miura, M. Org. Lett. 2005, 7, 1781. doi: 10.1021/ol0503743
7. [7]
  Shibata, K.; Satoh, T.; Miura, M. Adv. Synth. Catal. 2007, 349, 2317. doi: 10.1002/(ISSN)1615-4169
8. [8]
  Liao, T.-G.; Wang, Q.-A.; Fang, W.-Q.; Zhu, H.-J. Chin. J. Org. Chem. 2006, 26, 685 (in Chinese).
9. [9]
  Ye, S.; Gao, K.; Zhou, H.; Yang, X.; Wu, J. Chem. Commun. 2009, 45, 5406.
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沈阳化工大学材料科学与工程学院沈阳 110142