Citation: Wang Yonggang, Liu Renrong, Gao Jianrong, Jia Yixia. Palladium-Catalyzed Dearomative Decarboxylative Alkynylation of Indoles with Acetylenecarboxylic Acids[J]. Chinese Journal of Organic Chemistry, ;2017, 37(3): 691-697. doi: 10.6023/cjoc201608027 shu

Palladium-Catalyzed Dearomative Decarboxylative Alkynylation of Indoles with Acetylenecarboxylic Acids

College of Chemical Engineering, Zhejiang University of Technology, Hangzhou 310014

Corresponding author: Jia Yixia, yxjia@zjut.edu.cn
Received Date: 26 August 2016
Revised Date: 15 November 2016

Fund Project: the National Natural Science Foundation of China 21372202the National Natural Science Foundation of China 21522207

Figures(1)

A palladium-catalyzed indole dearomative arylalkynylation via decarboxylative coupling of alkynyl carboxylic acids and alkyl-palladium intermediates has been developed, which provides a reliable approach to a serious of structural diversely 2, 3-disubstituted indolines bearing vicinal tertiary and quaternary stereocenters in moderate to good yields and excellent diastereoselectivities.
- homogenous catalysis,
- palladium,
- indole,
- dearomatization,
- alkynylation
1. [1]
2. [2]
3. [3]
  (a) Pape, A. R.; Kaliappan, K. P.; Kündig, E. P. Chem. Rev. 2000, 100, 2917.
  (b) Wang, D.-S.; Chen, Q.-A.; Li, W.; Yu, C.-B.; Zhou, Y.-G.; Zhang, X. J. Am. Chem. Soc. 2010, 132, 8909.
  (c) Wang, D.-S.; Chen, Q.-A.; Lu, S.-M.; Zhou, Y.-G. Chem. Rev. 2012, 112, 2557.
  (d) Zhuo, C.-X.; Zhang, W.; You, S.-L. Angew. Chem., Int. Ed. 2012, 51, 12662.
  (e) Zhuo, C.-X.; Zheng, C.; You, S.-L. Acc. Chem. Res. 2014, 47, 2558.
  (f) Gao, R.-D.; Liu, C.; Dai, L.-X.; Zhang, W.; You, S.-L. Org. Lett. 2014, 16, 3919.
  (g) Du, K.; Guo, P.; Chen, Y.; Cao, Z.; Wang, Z.; Tang, W. Angew. Chem., Int. Ed. 2015, 54, 3033.
  (h) Roche, S. P.; Youte Tendoung, J.-J.; Treguier, B. Tetrahedron 2015, 3549.
  (i) Zhang, H.; Hu, R.-B.; Liu, N.; Li, S.-X.; Yang, S. Org. Lett. 2016, 18, 28.
  (j) Wu, W.-T.; Zhang, L.; You, S.-L. Chem. Soc. Rev. 2016, 45, 1570.
4. [4]
  (a) Zhang, X.; Yang, Z.-P.; Liu, C.; You, S.-L. Chem. Sci. 2013, 4, 3239.
  (b) Zhang, X.; Liu, W.-B.; Wu, Q.-F.; You, S.-L. Org. Lett. 2013, 15, 3746.
  (c) Spangler, J. E.; Davies, H. M. L. J. Am. Chem. Soc. 2013, 135, 6802.
  (d) Xiong. H.; Xu, H.; Liao, S.; Xie, Z.; Tang, Y. J. Am. Chem. Soc. 2013, 135, 7851.
  (e) Zhang, X.; Han, L.; You, S.-L. Chem. Sci. 2014, 5, 1059.
  (f) Tong, M.-C.; Chen, X.; Li, J.; Huang, R.; Tao, H.-Y.; Wang, C.-J. Angew.Chem., Int. Ed. 2014, 53, 4680.
  (g) Zhang, X.; Liu, W.-B.; Tu, H.-F.; You, S.-L. Chem. Sci. 2015, 6, 4525.
5. [5]
  (a) Wu, K.-J.; Dai, L.-X.; You, S.-L. Org. Lett. 2012, 14, 3772.
  (b) Zhao, L.; Li, Z.; Chang, L.; Xu, J.; Yao, H.; Wu, X. Org. Lett. 2012, 14, 2066.
6. [6]
  Shen, C.; Liu, R.-R.; Fan, R.-J.; Li, Y.-L.; Xu, T.-F.; Gao, J.-R.; Jia, Y.-X. J. Am. Chem. Soc. 2015, 137, 4936. doi: 10.1021/jacs.5b01705
7. [7]
  (a) Petrone, D. A.; Yen, A.; Zeidan, N.; Lautens, M. Org. Lett. 2015, 17, 4838.
  (b) Petrone, D. A.; Kondo, M.; Zeidan, N.; Lautens, M. Chem. Eur. J. 2016, 22, 5684.
8. [8]
  Liu, R.-R.; Xu, T.-F.; Wang, Y.-G.; Xiang, B.; Gao, J.; Jia, Y.-X. Chem. Commun. 2016, 52, 13664. doi: 10.1039/C6CC06262H
9. [9]
  (a) Goossen, L. J.; Rodríguez, N.; Melzer, B.; Linder, C.; Deng, G.; Levy, L. M. J. Am. Chem. Soc. 2007, 129, 4824.
  (b) Gooß en, L. J.; Rudolphi, F.; Oppel, C.; Rodriguez, N. Angew. Chem., Int. Ed. 2008, 47, 3043.
  (c) Kima, H.; Lee, P. H. Adv. Synth. Catcal. 2009, 351, 2827.
  (d) Xie, K.; Yang, Z.; Zhou, X.; Li, X.; Wang, S.; Tan, Z.; An, X.; Guo, C.-C. Org. Lett. 2010, 12, 1564.
  (e) Zhao, D.; Gao, C.; Su, X.; He, Y.; You, J.; Xue, Y. Chem. Commun. 2010, 46, 9049.
  (f) Park, A.; Park, K.; Kim, Y.; Lee, S. Org. Lett. 2011, 52, 944.
  (g) Hu, P.; Zhang, M.; Jie, X.; Su, W. Angew. Chem., Int. Ed. 2012, 51, 227.
  (h) Song, B.; Knauber, T.; Gooß en, L. J. Angew. Chem., Int. Ed. 2013, 52, 2954.
  (i) Fromm, A.; Vanllen Wullen, C.; Hackenberger, D.; Gooß en, L. J. J. Am. Chem. Soc. 2014, 136, 10007.
10. [10]
  Myers, A. G.; Tanaka, D.; Mannion, M. R. J. Am. Chem. Soc. 2002, 124, 11250. doi: 10.1021/ja027523m
11. [11]
  Gooßen, L. J.; Deng, G.; Levy, L. M. Science 2006, 313, 662. doi: 10.1126/science.1128684
12. [12]
  (a) Moon, J.; Jeong, M.; Nam, H.; Ju, J.; Moon, J. H.; Jung, H. M.; Lee, S. Org. Lett. 2008, 10, 945.
  (b) Moon, J.; Jang, M.; Lee, S. J. Org. Chem. 2009, 74, 1403.
  (c) Park, A.; Park, K.; Kim, Y.; Lee, S. Org. Lett. 2011, 52, 944.
13. [13]
  During our submission of this manuscript, Liang and co-workers reported a similar work, see:Che, S.; Wu, X.-X.; Wang, J.; Hao, X.-H.; Xia, Y.; Shen, Y.; Jing, H.; Liang, Y.-M. Org. Lett. 2016, 18, 4016. doi: 10.1021/acs.orglett.6b01711
14. [14]
  Cai, S.; Yang, K; Wang, D. Z. Org. Lett. 2014, 16, 2606. doi: 10.1021/ol501071k
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