Citation: Hao Erjun, Jiang Xiaohan, Fu Dandan, Wang Dongchao, Xie Mingsheng, Qu Guirong, Guo Haiming. Synthesis of 3-Cyanomethyl Oxoindoles via Palladium-Catalyzed Domino Heck/Cyanation Reaction in Water[J]. Chinese Journal of Organic Chemistry, ;2016, 36(11): 2746-2751. doi: 10.6023/cjoc201605039 shu

Synthesis of 3-Cyanomethyl Oxoindoles via Palladium-Catalyzed Domino Heck/Cyanation Reaction in Water

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Collaborative Innovation Center of Henan Province for Green Manufacturing of Fine Chemicals, Key Laboratory of Green Chemical Media and Reactions of Ministry of Education, School of Chemistry and Chemical Engineering, Henan Normal University, Xinxiang 453007

Corresponding author: Wang Dongchao, wangdc@htu.cn
Received Date: 22 May 2016
Revised Date: 28 June 2016

Fund Project: National Natural Science Foundation of China 21472037the Innovative Research Team in Science and Technology in University of Henan Province 15IRTSTHN003the Postdoctoral Science Foundation of Henan Province 2015071

Figures(1)

3-Cyanomethyl oxoindoles are a kind of important drug intermediates, which can be used to synthesize horsfiline, esermethole and physostigmine and other natural products via the conversion of cyano functional groups. aA domino Heck/cyanation reaction in aqueous was developed to afford 3-cyanomethyl oxoindole compounds. This method, using green medium water instead of organic solvents, without any basic additives, provided a green and efficient new procedure for the synthesis of 3-cyanomethyl oxoindoles.
- cyanation cascade reaction,
- Heck reaction,
- 3-cyanomethyl oxoindoles
1. [1]
  Grigg, R.; Sridharan, V. J. Organomet. Chem. 1999, 576, 65.
  (b) Lapierre, A. J. B.; Geib, S. J.; Curran, D. P. J. Am. Chem. Soc. 2007, 129, 494.
  (c) Tian, J.; Moeller, K. D. Org. Lett. 2005, 7, 5381.
  (d) Pei, W.; Shen, C.; Mo, J.; Xu, X.-L. Chin. J. Org. Chem. 2007, 27, 653 (in Chinese). (裴文, 沈忱, 莫峻, 许孝良, 有机化学, 2007, 27, 653.)
2. [2]
  Seashore-Ludlow, B.; Somfai, P. Org. Lett. 2012, 14, 3858..
  (b) Burns, B.; Grigg, R.; Sridharan, V.; Stevenson, P.; Sukirthalingam, S.; Worakun, T. Tetrahedron Lett. 1989, 30, 1135..
  (c) Grigg, R.; Sansano, J. M.; Santhakumar, V.; Sridharan, V.; Thangavelanthum, R.; Thornton-Pett, M.; Wilson, D. Tetrahedron 1997, 53, 11803.
  (d) Lee, C.-W.; Oh, K. S.; Kim, K. S.; Ahn, K. H. Org. Lett. 2000, 2, 1213.
  (e) Oh, C. H.; Sung, H. R.; Park, S. J.; Ahn, K. H. J. Org. Chem. 2002, 67, 7155.
3. [3]
  Piou, T.; Neuville, L.; Zhu, J. Org. Lett. 2012, 14, 3760..
  (b) René, O.; Lapointe, D.; Fagnou, K. Org. Lett. 2009, 11, 4560..
  (c) Pinto, A.; Neuville, L.; Retailleau, P.; Zhu, J. Org. Lett. 2006, 8, 4927.
4. [4]
  Petrone, D. A.; Malik, H. A.; Clemenceau, A.; Lautens, M. Org. Lett. 2012, 14, 4806. doi: 10.1021/ol302111y
5. [5]
  Priebbenow, D. L.; Stewart, S. G.; Pfeffer, F. M. Tetrahedron Lett. 2012, 53, 1468..
  (b) Wu, P.; Liu, H.; Tong, X. Tetrahedron Lett. 2012, 53, 4673..
  (c) Zang, Q.; Javed, S.; Porubsky, P.; Ullah, F.; Neuenswander, B.; Lushington, G. H.; Basha, F. Z.; Organ, M. G.; Hanson, P. R. ACS Comb. Sci. 2012, 14, 211..
  (d) Priebbenow, D. L.; Henderson, L. C.; Pfeffer, F. M.; Stewart, S. G. J. Org. Chem. 2010, 75, 1787.
6. [6]
  Tobrman, T.; Dvořák, D. Tetrahedron Lett. 2004, 45, 273.
  (b) Burns, B.; Grigg, R.; Santhakumar, V.; Sridharan, V.; Stevenson, P.; Worakun, T. Tetrahedron 1992, 48, 7297.
  (c) Grigg, R.; Loganathan, V.; Sridharan, V.; Stevenson, P.; Su-kirthalingam, S.; Worakun, T. Tetrahedron 1996, 52, 11479.
  (d) Peng, R.; Van Nieuwenhze, M. S. Org. Lett. 2012, 14, 1962.
  (e) Yang, X.; Ma, S.; Du, Y.; Tao, Y. Chin. J. Org. Chem. 2013, 33, 2325 (in Chinese). (杨晓梅, 马莎, 杜艳妮, 陶云海, 有机化学, 2013, 33, 2325.)
  (f) 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.
7. [7]
  Wang, D.-C.; Wang, H.-X.; Hao, E.-J.; Jiang, X.-H.; Xie, M.-S.; Qu, G.-R.; Guo, H.-M. Adv. Synth. Catal. 2016, 358, 494.
  (b) Bararjanian, M.; Balalaie, S.; Rominger, F.; Movassagh, B.; Bijanzadeh, H. R. J. Org. Chem. 2010, 75, 2806.
  (c) Zhou, M.-B.; Huang, X.-C.; Liu, Y.-Y.; Song, R.-J.; Li, J.-H. Chem. Eur. J. 2014, 20, 1843.
8. [8]
  Wang, D.-C.; Niu, H.-Y.; Xie, M.-S.; Qu, G.-R.; Wang, H.-X.; Guo, H.-M. Org. Lett. 2014, 16, 262. doi: 10.1021/ol4032683
9. [9]
  Jaegli, S.; Vors, J.-P.; Neuville, L.; Zhu, J. Synlett 2009, 2997.
10. [10]
  Pinto, A.; Jia, Y.; Neuville, L.; Zhu, J. Chem. Eur. J. 2007, 13, 961. doi: 10.1002/(ISSN)1521-3765
11. [11]
  Jaegli, S.; Vors, J.-P.; Neuville, L.; Zhu, J. Tetrahedron 2010, 66, 8911. doi: 10.1016/j.tet.2010.09.056
12. [12]
  Xia, R.; Xie, M.-S.; Niu, H.-Y.; Qu, G.-R.; Guo, H.-M. Green Chem. 2014, 16, 1077.
  (b) Qu, G.-R.; Wu, J.; Wu, Y.-Y.; Zhang, F.; Guo, H.-M. Green Chem. 2009, 11, 760.
  (c) Qu, G.-R.; Zhao, L.; Wang, D.-C.; Wu, J.; Guo, H.-M. Green Chem. 2008, 10, 287.
13. [13]
  Jing, C.; Shi, T.; Xing, D.; Guo, X.; Hu, W.-H. Green Chem. 2013, 15, 620.
  (b) Ma, J.; Han, B.; Song, J.; Hu, J.; Lu, W.; Yang, D.; Zhang, Z.; Jiang, T.; Hou, M. Green Chem. 2013, 15, 1485.
  (c) Shen, S.-C.; Sun, X.-W.; Lin, G.-Q. Green Chem. 2013, 15, 896.
  (d) Zhang, Y.; Wei, B.-W.; Lin, H.; Zhang, L.; Liu, J.-X.; Luo, H.-Q.; Fan, X.-L. Green Chem. 2015, 17, 3266.
  (e) Wang, Y.; Zhou, C.; Wang, R. Green Chem. 2015, 17, 3910.
14. [14]
  Liu, X.; Ma, X.; Huang, Y.; Gu, Z. Org. Lett. 2013, 15, 4814.
  (b) Grehn, L.; Gunnarsson, K.; Ragnarsson, U. J. Chem. Soc., Chem. Commun. 1985, 19, 1317.
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