Citation: Wei Huang, Ming-Liang Han, Yu-Wen Liu, Hui Xu, Hui-Xiong Dai. Palladium-catalyzed diarylative dearomatization of indoles with aryl thioesters[J]. Chinese Chemical Letters, ;2021, 32(9): 2765-2768. doi: 10.1016/j.cclet.2021.02.048 shu

Palladium-catalyzed diarylative dearomatization of indoles with aryl thioesters

    * Corresponding author at: Chinese Academy of Sciences Key Laboratory of Receptor Research, Shanghai Institute of Materia Medica, Shanghai 201203, China.
    ** Corresponding author.
    E-mail addresses: xuhui2018@simm.ac.cn (H. Xu), hxdai@simm.ac.cn (H.-X. Dai)
  • Received Date: 18 January 2021
    Revised Date: 20 February 2021
    Accepted Date: 22 February 2021
    Available Online: 25 February 2021

Figures(3)

  • We report herein a palladium-catalyzed diarylative dearomatization of indole by employing thioester and arylboronic acid as the aryl electrophiles. The reaction involved a decarbonylation/migratory insertion/terminal Suzuki coupling procedure. Substrates bearing various functional groups are well tolerated in the reaction, affording the diarylated indoline skeletons in moderate to good yields.
  • 加载中
    1. [1]

      (a) S. Marcos, R.F. Moro, I. Costales, P. Basabe, D. Diez, Nat. Prod. Rep. 30 (2013) 1509-1526;
      (b) P. Siengalewicz, T. Gaich, J. Mulzer, Angew. Chem. Int. Ed. 47 (2008) 8170-8176;
      (c) C. Avendano, C.E. Caballero, C. Mendez-Vidal, A.R. de Quesada, J.C. Menendez, Lett. Drug Des. Discov. 3 (2006) 369-377;
      (d) Y.J. Wu, Top. Heterocycl. Chem. 29 (2010) 1-29;
      (e) S.M. Verbitski, C.L. Mayne, R.A. Davis, G.P. Concepcion, C.M. Ireland, J. Org. Chem. 67 (2002) 7124-7126;
      (f) D. Zhang, H. Song, Y. Qin, Acc. Chem. Res. 44 (2011) 447-457.

    2. [2]

      (a) E.F. Rogers, H.R. Snyder, R.F. Fischer, J. Am. Chem. Soc. 74 (1952) 1987-1989;
      (b) H.R. Snyder, R.F. Fischer, J.F. Walker, H.E. Els, G.A. Nussberger, J. Am. Chem. Soc. 76 (1954) 2819-2825;
      (c) H.R. Snyder, R.F. Fischer, J.F. Walker, H.E. Els, G.A. Nussberger, J. Am. Chem. Soc. 76 (1954) 4601-4605.

    3. [3]

      (a) R.L. Noble, C.T. Beer, J.H. Cutts, Ann. N.Y. Acad. Sci. 76 (1958) 882-894;
      (b) G.H. Svoboda, N. Nuess, M. Gorman, J. Am. Pharm. Assoc. Sci. Ed. 48 (1959) 659-666.

    4. [4]

      (a) C. Zheng, S.L. You, Nat. Prod. Rep. 36 (2019) 1589-1605;
      (b) J. Song, D.F. Chen, L.Z. Gong, Natl. Sci. Rev. 4 (2017) 381-396;
      (c) S.P. Roche, J.J.Y. Tendoung, B. Tréguier, Tetrahedron 71 (2015) 3549-3591;
      (d) W. Zi, Z. Zuo, D. Ma, Acc. Chem. Res. 48 (2015) 702-711;
      (e) S.L. You, Asymmetric Dearomatization Reactions, Wiley-VCH, 2016;
      (f) T.B. Hua, C. Xiao, Q.Q. Yang, J.R. Chen Chin. Chem. Lett. 31 (2020) 311-323.

    5. [5]

      (a) N. Zeidan, M. Lautens, Synthesis 51 (2019) 4137-4146.

    6. [6]

      S. Brown, S. Clarkson, R. Grigg, et al., Tetrahedron 57(2001) 1347-1359.  doi: 10.1016/S0040-4020(00)01103-0

    7. [7]

      (a) R.B. Bedford, N. Fey, M.F. Haddow, R.F. Sankey, Chem. Commun. 47 (2011) 3649-3651;
      (b) L. Zhao, Z. Li, L. Chang, et al., Org. Lett. 14 (2012) 2066-2069;
      (c) K.J. Wu, L.X. Dai, S.L. You, Org. Lett. 14 (2012) 3772-3775;
      (d) R.R. Liu, T.F. Xu, Y.G. Wang, et al., Chem. Commun. 52 (2016) 13664-13667;
      (e) S. Chen, X.X. Wu, J. Wang, et al., Org. Lett. 18 (2016) 4016-4019;
      (f) D.A. Petrone, M. Kondo, N. Zeidan, M. Lautens, Chem. Eur. J. 22 (2016)5684-5691;
      (g)J.Q. Weng, L.L. Xing, W.R. Hou, R.X. Liang, Y.X. Jia, Org. Chem. Front. 6 (2019)1577-1580.

    8. [8]

      (a) C. Shen, R.R. Liu, R.J. Fan, et al., J. Am. Chem. Soc. 137 (2015) 4936-4939;
      (b) X.R. Qin, M.W.Y. Lee, J.R.S. Zhou, Angew. Chem. Int. Ed. 56 (2017) 12723-12726;
      (c) R.R. Liu, Y.G. Wang, Y.L. Li, et al., Angew. Chem. Int. Ed. 56 (2017) 7475-7478;
      (d) R.X. Liang, R.Z. Yang, R.R. Liu, Y.X. Jia, Org. Chem. Front. 5 (2018) 1840-1843;
      (e) X. Li, B. Zhou, R.Z. Yang, et al., J. Am. Chem. Soc. 140 (2018) 13945-13951;
      (f) C. Shen, N. Zeidan, Q. Wu, et al., Chem. Sci. 10 (2019) 3118-3122;
      (g) P. Yang, R.Q. Xu, C. Zheng, S.L. You, Chin. J. Chem. 38 (2020) 235-241;
      (h) A.D. Marchese, F. Lind, Á. E. Mahon, H. Yoon, M. Lautens, Angew. Chem. Int. Ed. 58 (2019) 5095-5099;
      (i) N. Zeidan, T. Beisel, R. Ross, M. Lautens, Org. Lett. 20 (2018) 7332-7335.

    9. [9]

      (a) E.J. Corey, K.C. Nicolaou, J. Am. Chem. Soc. 96 (1974) 5614-5616;
      (b) K.C. Nicolaou, Tetrahedron 33 (1977) 683-710;
      (c) J. Staunton, K.J. Weissman, Nat. Prod. Rep. 18 (2001) 380-416;
      (d) B. Zhou, Faridoon, X. Tian, et al., Chin. Chem. Lett. 29 (2018) 1123-1126;
      (e) Y. Zheng, F. Wu, S. Ling, J.B. Li, C. Tian, Chin. Chem. Lett. 31 (2020) 1267-1270;
      (f) J. Hu, P. Zhu, Y. Li, Y. Chen, Chin. Chem. Lett. 29 (2018) 1043-1050.

    10. [10]

      (a) H. Prokopcová, C.O. Kappe, Angew. Chem. Int. Ed. 48 (2009) 2276-2286;
      (b) L. Wang, W. He, Z.K. Yu, Chem. Soc. Rev. 42 (2013) 599-621;
      (c) S.G. Modha, V.P. Mehtaz, E.V.V. Eycken, Chem. Soc. Rev. 42 (2013) 5042-5055;
      (d) H.G. Cheng, H. Chen, Y. Liu, Q.H. Zhou, Asian J. Org. Chem. 7 (2018) 490-508;
      (e) V. Hirschbeck, P.H. Gehrtz, I. Fleischer, Chem. Eur. J. 24 (2018) 7092-7107;
      (f) T. Fukuyama, H. Tokuyama, Aldrichimica Acta 37 (2004) 87-96;
      (g) Y.Q. Peng, L.C. Luo, J. Gong, J. Huang, Q. Sun, Chin. Chem. Lett. 26 (2015) 1016-1018.

    11. [11]

      (a) H. Tokuyama, S. Yokoshima, T. Yamashita, T. Fukuyama, Tetrahedron Lett. 39 (1998) 3189-3192;
      (b) L.S. Liebeskind, J. Srogl, J. Am. Chem. Soc. 122 (2000) 11260-11261;
      (c) J.M. Villalobos, J. Srogl, L.S. Liebeskind, J. Am. Chem. Soc. 129 (2007) 15734-15735;
      (d) H. Prokopcov, C.O. Kappe, Angew. Chem. Int. Ed. 47 (2008) 3674-3676;
      (e) X. Yi, Y.F. Cao, X. Wang, et al., Tetrahedron Lett. 61 (2020) 151780-151782.

    12. [12]

      (a) T. Fukuyama, S.C. Lin, L. Li, J. Am. Chem. Soc. 112 (1990) 7050-7051;
      (b) H. Tokuyama, S. Yokoshima, S.C. Lin, L. Li, T. Fukuyama, Synthesis 8 (2002) 1121-1123.

    13. [13]

      F. Sun, M. Li, C. He, et al., J. Am. Chem. Soc. 138(2016) 7456-7459.  doi: 10.1021/jacs.6b02495

    14. [14]

      (a) K. Osakada, T. Yamamoto, A. Yamamoto, Tetrahedron Lett. 28 (1987) 6321-6324;
      (b) N. Ichiishi, C.A. Malapit, Ł. Wo zniak, M.S. Sanford, Org. Lett. 20 (2018) 44-47;
      (c) C.W. Liu, M. Szostak, Chem. Commun. 54 (2018) 2130-2133;
      (d) C.E. Brigham, C.A. Malapit, N. Lalloo, M.S. Sanford, ACS Catal. 10 (2020) 8315-8320;
      (e) F. Yamashita, H. Kuniyasu, J. Terao, N. Kambe, Org. Lett. 10 (2008) 101-104;
      (f) E. Wenkert, D. Chianelli, J. Chem. Soc. Chem. Commun. (1991) 627-628.

    15. [15]

      H. Ochiai, Y. Uetake, T. Niwa, T. Hosoya, Angew. Chem. Int. Ed. 56(2017) 2482-2486.  doi: 10.1002/anie.201611974

    16. [16]

      M. Han, W. Huang, Y. Liu, et al., Org. Lett. 23(2021) 172-177.  doi: 10.1021/acs.orglett.0c03897

  • 加载中
    1. [1]

      Rongjian ChenJiahui LiuCaixia LinYuanming LiYanhou GengYaofeng Yuan . Synthesis and properties of tetraphenylethene cationic cyclophanes based on o-carborane skeleton. Chinese Chemical Letters, 2024, 35(12): 110074-. doi: 10.1016/j.cclet.2024.110074

    2. [2]

      Aimin FuChunmei ChenQin LiNanjin DingJiaxin DongYu ChenMengsha WeiWeiguang SunHucheng ZhuYonghui Zhang . Niduenes A−F, six functionalized sesterterpenoids with a pentacyclic 5/5/5/5/6 skeleton from endophytic fungus Aspergillus nidulans. Chinese Chemical Letters, 2024, 35(9): 109100-. doi: 10.1016/j.cclet.2023.109100

    3. [3]

      Zhuo LiPeng YuDi ShenXinxin ZhangZhijian LiangBaoluo WangLei Wang . Low-loading Pt anchored on molybdenum carbide-based polyhedral carbon skeleton for enhancing pH-universal hydrogen production. Chinese Chemical Letters, 2025, 36(4): 109713-. doi: 10.1016/j.cclet.2024.109713

Metrics
  • PDF Downloads(11)
  • Abstract views(615)
  • HTML views(51)

通讯作者: 陈斌, bchen63@163.com
  • 1. 

    沈阳化工大学材料科学与工程学院 沈阳 110142

  1. 本站搜索
  2. 百度学术搜索
  3. 万方数据库搜索
  4. CNKI搜索
Address:Zhongguancun North First Street 2,100190 Beijing, PR China Tel: +86-010-82449177-888
Powered By info@rhhz.net

/

DownLoad:  Full-Size Img  PowerPoint
Return