Citation: Liu Ruiting, Li Zhen, Wang Shengke, Zhou Xigeng. Pd(OAc)₂/CuI-Catalyzed Tandem Reaction for Synthesis of Polysubstituted 3-Chalcogenylindoles[J]. Chinese Journal of Organic Chemistry, ;2019, 39(11): 3215-3222. doi: 10.6023/cjoc201904032 shu

Pd(OAc)₂/CuI-Catalyzed Tandem Reaction for Synthesis of Polysubstituted 3-Chalcogenylindoles

Liu Ruiting ^a ,
Li Zhen ^a ,
Wang Shengke ^a ,
Zhou Xigeng ^a,b,,

a.
Department of Chemistry, Fudan University, Shanghai 200438
b.
State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032

Corresponding author: Zhou Xigeng, xgzhou@fudan.edu.cn
Received Date: 12 April 2019
Revised Date: 18 June 2019
Available Online: 2 November 2019
Fund Project: the National Natural Science Foundation of China 21732007the National Natural Science Foundation of China 21572034the National Natural Science Foundation of China 21871054Project supported by the National Natural Science Foundation of China (Nos. 21572034, 21732007, 21871054)

Figures(5)

Tandem Pd(OAc)₂/CuI catalyzed coupling/cyclization/chalcogenylation reaction of gem-dibromovinylanilines with boronic acids and dichalcogenides has been developed, which provides a new synthetic approach to 3-sulfenyl-and 3-selenylindoles. Various functional groups such as methoxyl, halides and trifluoromethyl groups in the substrates are tolerated.
- indole,
- Pd(OAc)₂/CuI,
- catalysis,
- synthesis
1. [1]
  (a) Stempel, E.; Gaich, T. Acc. Chem. Res. 2016, 49, 2390.
  (b) Sundberg, R. L. Indoles, Academic Press, London, 1996.
  (c) Katritzky, A. R.; Pozharskii, A. F. Handbook of Heterocyclic Chemistry, Pergamon, Oxford, 2000.
  (d) Gribble, G. W. J. Chem. Soc., Perkin Trans. 1 2000, 1045.
  (e) Kochanowska-Karamyan, A. J.; Harmann, M. T. Chem. Rev. 2010, 110, 4489.
  (f) Shiri, M. Chem. Rev. 2012, 112, 3508.
2. [2]
  (a) Gao, S. S.; Li, X. M.; Williams, K.; Proksch, P.; Ji, N. Y.; Wang, B. G. J. Nat. Prod. 2016, 79, 2066.
  (b) Cheng, G. G.; Li, D.; Hou, B.; Li, X.-N.; Liu, L.; Chen, Y. Y.; Lunga, P. K.; Khan, A.; Liu, Y. P.; Zuo, Z. L.; Luo, X. D. J. Nat. Prod. 2016, 79, 2158.
  (c) Sim, D. S. Y.; Teoh, W. Y.; Sim, K. S.; Lim, S. H.; Thomas, N. F.; Low, Y. Y.; Kam, T. S. J. Nat. Prod. 2016, 79, 1048.
  (d) Wang, Z. R.; Hu, J. H.; Yang, X. P.; Feng, X.; Li, X. S.; Huang, L.; Chan, A. S. C. J. Med. Chem. 2018, 61, 1871.
3. [3]
  (a) Ragno, R.; Coluccia, A.; Regina, G. L.; Martino, G. D.; Piscitelli, F.; Lavecchia, A.; Novellino, E.; Bergamini, A.; Ciaprini, C.; Sinistro, A.; Maga, G.; Crespan, E.; Artico, M.; Silvestri, R. J. Med. Chem. 2006, 49, 3172.
  (b) Famiglini, V.; La Regina, G.; Coluccia, A.; Pelliccia, S.; Brancale, A.; Maga, G.; Crespan, E.; Badia, R.; Riveira-Muñoz, E.; Esté, J. A.; Ferretti, R.; Cirilli, R.; Zamperini, C.; Botta, M.; Schols, D.; Limongelli, V.; Agostino, B.; Novellino, E.; Silvestri R. J. Med. Chem. 2014, 57, 9945.
  (c) Famiglini, V.; La Regina, G.; Coluccia, A.; Masci, D.; Brancale, A.; Badia, R.; Riveira-Muñoz, E.; Esté, J. A. Crespan, E.; Brambilla, A.; Maga, G.; Catalano, M.; Limatola, C.; Formica, F. R.; Cirilli, R.; Novellino, E.; Silvestri, R. J. Med. Chem. 2017, 60, 6528.
  (d) Li, X; Gao, P.; Huang, B. S.; Zhou, Z. X.; Yu, Z.; Yuan, Z.; Liu, H. Q.; Pannecouque, C.; Daelemans, D.; De Clercq, E. Eur. J. Med. Chem. 2017, 126, 190.
  (e) Duchowicz1, P. R.; BaceloSilvina, D. E.; Fioressi, S. E.; Palermo, V.; Ibezim, N. E.; Romanelli, G. P. Med. Chem. Res. 2018, 27, 420.
4. [4]
  (a) Regina, G. L.; Edler, M. C.; Brancale, A.; Kandil, S.; Coluccia, A.; Piscitelli, F.; Hamel, E.; Martino, G. D.; Matesanz, R.; Díaz, J. F.; Scovassi, A. I.; Prosperi, E.; Lavecchia, A.; Novellino, E.; Artico, M.; Silvestri, R. J. Med. Chem. 2007, 50, 2865.
  (b) La Regina, G.; Bai, R.; Coluccia, A.; Famiglini, V.; Pelliccia, S.; Passacantilli, S.; Mazzoccoli, C.; Ruggieri, V.; Verrico, A.; Miele, A.; Monti, L.; Nalli, M.; Alfonsi, R.; Di Marcotullio, L.; Gulino, A.; Ricci, B.; Soriani, A.; Santoni, A.; Caraglia, M.; Porto, S.; Da Pozzo, E.; Martini, C.; Brancale, A.; Marinelli, L.; Novellino, E.; Vultaggio, S.; Varasi, M.; Mercurio, C.; Bigogno, C.; Dondio, G.; Hamel, E.; Lavia, P.; Silvestri, R. J. Med. Chem. 2015, 58, 5789.
  (c) Sidhu, J. S.; Singla, R.; Mayank, Jaitak. V. Anti-Cancer Agents Med. Chem. 2016, 16, 160.
5. [5]
  Ramakrishna, V. S. N.; Shirsath, V. S.; Kambhampati, R. S.; Vishwakarma, S.; Kandikere, N. V.; Kota, S.; Jasti. V. WO 2007020653, 2007.
6. [6]
  Hu, X.; Compton, J. R.; AbdulHameed, M. D. M.; Marchand, C. L.; Robertson, K. L.; Leary, D. H.; Jadhav, A.; Hershfield, J. R.; Wallqvist, A.; Friedlander, A. M.; Legler, P. M. J. Med. Chem. 2013, 56, 5275. doi: 10.1021/jm4001242
7. [7]
  (a) Unangst, P. C.; Connor, D. T.; Stabler, S. R.; Weikert, R. J.; Carethers, M. E.; Kennedy, J. A.; Thueson, D. O.; Chestnut, J. C.; Adolphson, R. L.; Conroy, M. C. J. Med. Chem. 1989, 32, 1360.
  (b) Armer, R. E.; Wynne, G. M. WO 2008012511, 2008.
8. [8]
  Nuth, M.; Guan, H.; Zhukovskaya, N.; Saw, Y. L.; Ricciardi, R. P. J. Med. Chem. 2013, 56, 3235. doi: 10.1021/jm301735k
9. [9]
  (a) Hamel, P. J. Org. Chem. 2002, 67, 2854.
  (b) Vedejs, E.; Little, J. D. J. Org. Chem. 2004, 69, 1794.
  (c) Li, J. X.; An, Y. N.; Li, J. W.; Yang, S. R.; Wu, W. Q.; Jiang, H. F. Org. Chem. Front. 2017, 4, 1590.
10. [10]
  (a) Montevecchi, P. C.; Navacchia, M. L.; Spagnolo, P. Eur. J. Org. Chem. 1998, 6, 1219.
  (b) Chen, Y.; Cho, C. H.; Larock, R. C. Org. Lett. 2009, 11, 173.
  (c) Guo, Y. J.; Tang, R. Y.; Li, J. H.; Zhong, P.; Zhang, X. G. Adv. Synth. Catal. 2009, 351, 2615.
  (d) Kumar, P. P.; Reddy, Y. D.; Reddy, C. V. R.; Devi, B. R.; Dubey, P. K. J. Sulfur Chem. 2014, 35, 356.
  (e) Yang, Y.; Zhang, S.; Tang, L.; Hu, Y. B.; Zha, Z. G.; Wang, Z. Y. Green Chem. 2016, 18, 2609.
  (f) Li, J.; Cai, Z. J.; Wang, S. Y.; Ji, S. J. Org. Biomol. Chem. 2016, 14, 9384.
  (g) Guo, W.; Tan, W.; Zhao, M. M.; Tao, K. L.; Zheng, L. Y.; Wu, Y. Q.; Chen, D. L.; Fan, X. L. RSC Adv. 2017, 7, 37739.
  (h) Liao, H. X.; Yang, Y.; Li, W. M.; Shen, C.; Zhang, P. F. Curr. Org. Chem. 2017, 21, 2509.
  (i) Šiaučiulis, M.; Sapmaz, S.; PulisA, P.; Procter, D. J. Chem. Sci. 2018, 9, 754.
  (j) Li, J. X.; Li, C. S.; Yang, S. R.; An, Y. N.; Wu, W. Q.; Jiang, H. F. J. Org. Chem. 2016, 81, 2875.
  (k) Lavekar, A. G.; Equbal, D.; Saima; Sinha, A. K. Adv. Synth. Catal. 2018, 360, 180.
11. [11]
  Li, Z.; Hong, L. C.; Liu, R. T.; Shen, J. Z.; Zhou, X. G. Tetrahedron Lett. 2011, 52, 1343. doi: 10.1016/j.tetlet.2011.01.052
12. [12]
  (a) Kumar, D. R.; Satyanarayana, G. Org. Lett. 2015, 17, 5894.
  (b) Liu, H.; Xi, F. G.; Sun, W.; Yang, N. N.; Gao, E. Q. Inorg. Chem. 2016, 55, 5753.
  (c) Corma, A.; Navas, J.; Sabater, M. J. Chem. Rev. 2018, 118, 1410.
  (d) Korvorapun, K.; Kaplaneris, N.; Rogge, T.; Warratz, S.; Stückl, A. C.; Ackermann, L. ACS Catal. 2018, 8, 886.
13. [13]
  (a) Fang, Y. Q.; Lautens, M. Org. Lett. 2005, 7, 3549.
  (b) Fang, Y. Q.; Lautens, M. J. Org. Chem. 2008, 73, 538.
  (c) Chai, D. I.; Lautens, M. J. Org. Chem. 2009, 74, 3054.
  (d) Arthuis, M.; Pontikis, R.; Florent, J. C. Org. Lett. 2009, 11, 4608.
14. [14]
  Li, Z.; Hong, J. Q.; Zhou, X. G. Tetrahedron 2011, 67, 3690. doi: 10.1016/j.tet.2011.03.067
15. [15]
  CCDC 861518 for 4f contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Center via www.ccdc.cam.ac.uk/datarequest/cif.
16. [16]
  (a) Blanco, G. A.; Baumgartner, M. T. Tetrahedron Lett. 2011, 52, 7061.
  (b) Yan, G. b.; Borah, A. J.; Wang, L. G. Org. Biomol. Chem. 2014, 12, 9557.
  (c) Zhao, X.; Li, T. J.; Zhang, L. P.; Lu, K. Org. Biomol. Chem. 2016, 14, 1131.
17. [17]
  (a) Taniguchi, N. J. Org. Chem. 2006, 71, 7874.
  (b) Stein, A.; Alves, D.; da Rocha, J.; Nogueira, C.; Zeni, G. Org. Lett. 2008, 10, 4983.
  (c) Taniguchi, N. Tetrahedron 2009, 65, 2782.
  (d) Wu, W.; Ding, Y. C.; Xie, P.; Tang, Q. J.; Pittman Jr. C. U.; Zhou, A. H. Tetrahedron 2017, 73, 2151.
18. [18]
  (a) Ali, M. H.; McDermott, M. Tetrahedron Lett. 2002, 43, 6271.
  (b) Kabalka, G. W.; Reddy, M. S.; Yao, M. L. Tetrahedron Lett. 2009, 50, 7340.
  (c) Singh, D.; Deobald, A. M.; Camargo, L. S.; Tabarelli, G.; Rodrigues, O. D.; Braga, A. L. Org. Lett. 2010, 12, 3288.
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Pd(OAc)2/CuI-Catalyzed Tandem Reaction for Synthesis of Polysubstituted 3-Chalcogenylindoles

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Pd(OAc)₂/CuI-Catalyzed Tandem Reaction for Synthesis of Polysubstituted 3-Chalcogenylindoles