Citation: Zhou Quanlong, Zhu Changlei, Wu Ge, Zhang Yuanfei, Zhang Min, Su Weiping. Construction of Carbazoles by Palladium-Catalyzed Direct Cross-Coupling of Indoles with in situ Generated Aryl Vinyl Ketones[J]. Chinese Journal of Organic Chemistry, ;2017, 37(10): 2655-2662. doi: 10.6023/cjoc201705014 shu

Construction of Carbazoles by Palladium-Catalyzed Direct Cross-Coupling of Indoles with in situ Generated Aryl Vinyl Ketones

  • Corresponding author: Zhang Min, zhangmin@fjirsm.ac.cn Su Weiping, wpsu@fjirsm.ac.cn
  • 共同第一作者(These authors contributed equally to this work)
  • Received Date: 8 May 2017
    Revised Date: 6 July 2017
    Available Online: 11 October 2017

    Fund Project: the National Natural Science Foundation of China 21431008the National Natural Science Foundation of China 21602221the National Natural Science Foundation of China 21332001Project supported by the National Natural Science Foundation of China (Nos. 21431008, 21332001, 21602221, u1505242)the National Natural Science Foundation of China u1505242

Figures(2)

  • The synthesis of carbazoles via Pd-catalyzed direct cross-coupling of indoles with in situ generated aryl vinyl ketones by using statured ketones as the olefins source is described. This protocol obviates the need for additional preparation steps of aryl vinyl ketones and therefore opens up a new door to synthesis of carbazoles in an atom-and step-economical fashion.
  • 加载中
    1. [1]

      (a) Zhang, F. -F. ; Gan, L. -L. ; Zhou, C. -H. Bioorg. Med. Chem. Lett. 2010, 20, 1881.
      (b) Blunt, J. W. ; Copp, B. R. ; Munro, M. H. G. ; Northcote, P. T. ; Prinsep, M. R. Nat. Prod. Rep. 2003, 20, 1.
      (c) Deslandes, S. ; Chassaing, S. ; Delfourne, E. Mar. Drugs 2009, 7, 754.
      (d) Maneerat, W. ; Ritthiwigrom, T. ; Cheenpracha, S. ; Promgool, T. ; Yossathera, K. ; Deachathai, S. ; Phakhodee, W. ; Laphookhieo, S. J. Nat. Prod. 2012, 75, 741.

    2. [2]

      (a) Roy, J. ; Jana, A. K. ; Mal, D. Tetrahedron 2012, 68, 6099.
      (b) Knölker, H. -J. ; Reddy, K. R. Chem. Rev. 2002, 102, 4303.
      (c) Schmidt, A. W. ; Reddy, K. R. ; Knölker, H. -J. Chem. Rev. 2012, 112, 3193.

    3. [3]

      (a) Ackermann, L. ; Vicente, R. ; Kapdi, A. R. Angew. Chem. , Int. Ed. 2009, 48, 9792.
      (b) Lyons, T. W. ; Sanford, M. S. Chem. Rev. 2010, 110, 1147.
      (c) Liu, C. ; Zhang, H. ; Shi, W. ; Lei, A. Chem. Rev. 2011, 111, 1780.
      (d) Yeung, C. S. ; Dong, V. M. Chem. Rev. 2011, 111, 1215.

    4. [4]

      Zhao, J.; Larock, R. C. J. Org. Chem. 2006, 71, 5340.  doi: 10.1021/jo060727r

    5. [5]

      (a) Tsang, W. C. P. ; Zheng, N. ; Buchwald, S. L. J. Am. Chem. Soc. 2005,127, 14560.
      (b) Jordan-Hore, J. A. ; Johansson, C. C. ; Beck, E. M. ; Gaunt, M. J. J. Am. Chem. Soc. 2008, 130, 16184.
      (c) Cho, S. H. ; Yoon, J. ; Chang, S. J. Am. Chem. Soc. 2011, 133, 5996.
      (d) Takamatsu, K. ; Hirano, K. ; Satoh, T. ; Miura, M. Org. Lett. 2014, 16, 2892.

    6. [6]

      (a) Yamashita, M. ; Horiguchi, H. ; Hirano, K. ; Satoh, T. ; Miura, M. J. Org. Chem. 2009, 74, 7481.
      (b) Jia, J. ; Shi, J. ; Zhou, J. ; Liu, X. ; Song, Y. ; Xu, H. E. ; Yi, W. Chem. Commun. 2015, 51, 2925.

    7. [7]

      (a) Ozaki, K. ; Zhang, H. ; Ito, H. ; Lei, A. ; Itami, K. Chem. Sci. 2013, 4, 3416.
      (b) Verma, A. K. ; Danodia, A. K. ; Saunthwal, R. K. ; Patel, M. ; Choudhary, D. Org. Lett. 2015, 17, 3658.
      (c) Laha, J. K. ; Dayal, N. Org. Lett 2015, 17, 4742.
      (d) Chen, S. ; Li, Y. ; Ni, P. ; Huang, H. ; Deng, G. J. Org. Lett 2016.

    8. [8]

      Grimster, N. P.; Gauntlett, C.; Godfrey, C. R.; Gaunt, M. J. Angew. Chem., Int. Ed. 2005, 44, 3125.  doi: 10.1002/(ISSN)1521-3773

    9. [9]

      Guo, T.; Jiang, Q.; Huang, F.; Chen, J.; Yu, Z. Org. Chem. Front. 2014, 1, 707.  doi: 10.1039/C4QO00122B

    10. [10]

      (a) Muzart, J. Eur. J. Org. Chem. 2010, 3779.
      (b) Newhouse, T. ; Turlik, A. ; Chen, Y. Synlett 2016, 27, 331.

    11. [11]

      (a) Nicolaou, K. C. ; Gray, D. L. F. ; Montagnon, T. ; Harrison, S. T. Angew. Chem. , Int. Ed. 2002, 41, 996.
      (b) Nicolaou, K. C. ; Montagnon, T. ; Baran, P. S. Angew. Chem. , Int. Ed. 2002, 41, 993.
      (c) Nicolaou, K. C. ; Montagnon, T. ; Baran, P. S. ; Zhong, Y. L. J. Am. Chem. Soc. 2002, 124, 2245.
      (d) Uyanik, M. ; Akakura, M. ; Ishihara, K. J. Am. Chem. Soc. 2009, 131, 251. (e) Nicolaou, K. C. ; Zhong, Y. L. ; Baran, P. S. J. Am. Chem. Soc. 2000, 122, 7596.

    12. [12]

      (a) Bhattacharya, A. ; DiMichele, L. M. ; Dolling, U. H. ; Douglas, A. W. ; Grabowski, E. J. J. J. Am. Chem. Soc. 1988, 110, 3318.
      (b) Walker, D. ; Hiebert, J. D. Chem. Rev. 1967, 67, 153.

    13. [13]

      (a) Diao, T. ; Stahl, S. S. J. Am. Chem. Soc. 2011, 133, 14566.
      (b) Gao, W. M. ; He, Z. Q. ; Qian, Y. ; Zhao, J. ; Huang, Y. Chem. Sci. 2012, 3, 883.
      (c) Diao, T. ; Wadzinski, T. J. ; Stahl, S. S. Chem. Sci. 2012, 3, 887.
      (d) Diao, T. ; Pun, D. ; Stahl, S. S. J. Am. Chem. Soc. 2013, 135, 8205.
      (e) Bigi, M. A. ; White, M. C. J. Am. Chem. Soc. 2013, 135, 7831.

    14. [14]

      (a) Zhang, M. ; Zhang, Y. ; Jie, X. ; Zhao, H. ; Li, G. ; Su, W. Org. Chem. Front. 2014, 1, 843.
      (b) Wei, Y. ; Hu, P. ; Zhang, M. ; Su, W. Chem. Rev. 2017.

    15. [15]

      (a) Zhang, M. ; Zhou, J. ; Kan, J. ; Wang, M. ; Su, W. ; Hong, M. Chem. Commun. 2010, 46, 5455.
      (b) Zhou, J. ; Wu, G. ; Zhang, M. ; Jie, X. ; Su, W. Chem. -Eur. J. 2012, 18, 8032.
      (c) Zhang, M. ; Hu, P. ; Zhou, J. ; Wu, G. ; Huang, S. ; Su, W. Org. Lett. 2013, 15, 1718.
      (d) Shang, Y. ; Jie, X. ; Zhou, J. ; Hu, P. ; Huang, S. ; Su, W. Angew. Chem. Int. Ed. 2013, 52, 1299.

    16. [16]

      Jie, X.; Shang, Y.; Zhang, X.; Su, W. J. Am. Chem. Soc. 2016, 138, 5623.  doi: 10.1021/jacs.6b01337

    17. [17]

      Xiao, B.; Li, Y. M.; Liu, Z. J.; Yang, H. Y.; Fu, Y. Chem. Commun. 2012, 48, 4854.  doi: 10.1039/c2cc31737k

    18. [18]

      Klare, H. F.; Oestreich, M.; Ito, J.; Nishiyama, H.; Ohki, Y.; Tatsumi, K. J. Am. Chem. Soc. 2011, 133, 3312.  doi: 10.1021/ja111483r

    19. [19]

      Taylor, J. E.; Jones, M. D.; Williams, J. M. J.; Bull, S. D. Org. Lett. 2010, 12, 5740.  doi: 10.1021/ol1025348

    20. [20]

      Qi, T.; Qiu, W.; Liu, Y.; Zhang, H.; Gao, X.; Liu, Y.; Lu, K.; Du, C.; Yu, G.; Zhu, D. J. Org. Chem. 2008, 73, 4638.  doi: 10.1021/jo800622y

  • 加载中
    1. [1]

      Pengfei ZhangQingxue MaZhiwei JiangXiaohua XuZhong Jin . Transition-metal-catalyzed remote meta-C—H alkylation and alkynylation of aryl sulfonic acids enabled by an indolyl template. Chinese Chemical Letters, 2024, 35(8): 109361-. doi: 10.1016/j.cclet.2023.109361

    2. [2]

      Junqi SuWenhao LiuJianjun WangWeifen LuoYangyang MaLeiyang LvZhiping Li . Palladium-catalyzed ring-opening defluorinative cross-coupling of gem-difluorocyclopropanes with fluoromalonates or fluorobis(phenylsulfonyl)methane. Chinese Chemical Letters, 2026, 37(3): 111288-. doi: 10.1016/j.cclet.2025.111288

    3. [3]

      Shihaozhi WangJia-Hui ShiShan XuXue-Jing ZhangMing Yan . Palladium-catalyzed carbene C-H insertion reaction of non-activated arenes. Chinese Chemical Letters, 2026, 37(4): 111225-. doi: 10.1016/j.cclet.2025.111225

    4. [4]

      Giulia BrufaniEdoardo BazzicaYanlong GuFrancesco MaurielloLuigi Vaccaro . Csp2–H functionalization as an efficient catalytic route to carbazoles. Chinese Chemical Letters, 2026, 37(1): 111545-. doi: 10.1016/j.cclet.2025.111545

    5. [5]

      Yuhan LiuJingyang ZhangGongming YangJian Wang . Highly enantioselective carbene-catalyzed δ-lactonization via radical relay cross-coupling. Chinese Chemical Letters, 2025, 36(1): 109790-. doi: 10.1016/j.cclet.2024.109790

    6. [6]

      Jiyang LiuXiangzhang TaoZhenlei ZouJia XuHui ShuYi PanWeigang ZhangShengyang NiYi Wang . Modular and practical synthesis of gem-difluoroalkenes via consecutive Ni-catalyzed reductive cross-coupling. Chinese Chemical Letters, 2025, 36(7): 110461-. doi: 10.1016/j.cclet.2024.110461

    7. [7]

      Jie LiuJialin MingDa-Gang Yu . Photoexcited Ni-catalyzed regioselective cross-coupling of aryl chlorides with multifluoroarenes. Chinese Chemical Letters, 2026, 37(5): 112260-. doi: 10.1016/j.cclet.2025.112260

    8. [8]

      Jialin HuangLiying FuZhanyong TangXiaoqiang MaXingda ZhaoDepeng Zhao . Cross-coupling of trifluoromethylarenes with alkynes C(sp)-H bonds and azoles C(sp2)-H bonds via photoredox/copper dual catalysis. Chinese Chemical Letters, 2025, 36(7): 110505-. doi: 10.1016/j.cclet.2024.110505

    9. [9]

      Peng GuoShicheng DongXiang-Gui ZhangBing-Bin YangJun ZhuKe-Yin Ye . Cobalt-catalyzed migratory carbon-carbon cross-coupling of borabicyclo[3.3.1]nonane (9-BBN) borates. Chinese Chemical Letters, 2025, 36(4): 110052-. doi: 10.1016/j.cclet.2024.110052

    10. [10]

      Rong-Nan YiJun JiangWei-Min He . Pd/NHC-catalyzed ring-opening cross-coupling of gem-difluorocyclopropanes via a 3,3′-reductive elimination pathway. Chinese Chemical Letters, 2026, 37(4): 112163-. doi: 10.1016/j.cclet.2025.112163

    11. [11]

      Qinghong ZhangQiao ZhaoXiaodi WuLi WangKairui ShenYuchen HuaCheng GaoYu ZhangMei PengKai Zhao . Visible-light-induced ring-opening cross-coupling of cycloalcohols with vinylazaarenes and enones via β-C-C scission enabled by proton-coupled electron transfer. Chinese Chemical Letters, 2025, 36(2): 110167-. doi: 10.1016/j.cclet.2024.110167

    12. [12]

      Wei-Bin LiXiao-Chao HuangPei LiuJie KongGuo-Ping Yang . Recent advances in directing group assisted transition metal catalyzed para-selective C-H functionalization. Chinese Chemical Letters, 2025, 36(6): 110543-. doi: 10.1016/j.cclet.2024.110543

    13. [13]

      Junlong TangYuhan ZhaoYangbin JinLiren ZhangYuanfang WangWanqing WuHuanfeng Jiang . Palladium-catalyzed modular biomimetic synthesis of lignans derivatives. Chinese Chemical Letters, 2025, 36(7): 110969-. doi: 10.1016/j.cclet.2025.110969

    14. [14]

      Fuyang YueMingxing LiFei YuanHongjian SongYuxiu LiuQingmin Wang . Deboronative cross-coupling enabled by nickel metallaphotoredox catalysis. Chinese Chemical Letters, 2025, 36(12): 111053-. doi: 10.1016/j.cclet.2025.111053

    15. [15]

      Yuemin ChenYunqi WuGuoao WangFeihu CuiHaitao TangYingming Pan . Electricity-driven enantioselective cross-dehydrogenative coupling of two C(sp3)-H bonds enabled by organocatalysis. Chinese Chemical Letters, 2024, 35(9): 109445-. doi: 10.1016/j.cclet.2023.109445

    16. [16]

      Jian HanLi-Li ZengQin-Yu FeiYan-Xiang GeRong-Hui HuangFen-Er Chen . Recent advances in remote C(sp3)–H functionalization via chelating group-assisted metal-catalyzed chain-walking reaction. Chinese Chemical Letters, 2024, 35(11): 109647-. doi: 10.1016/j.cclet.2024.109647

    17. [17]

      Wenze ShiYang DongXihong WangMin WangJian Liao . SOP-ligand enabled palladium-catalyzed enantioselective anti-Markovnikov hydrothioesterification of α-substituted styrenes. Chinese Chemical Letters, 2025, 36(11): 111023-. doi: 10.1016/j.cclet.2025.111023

    18. [18]

      Tianzhu QinWeiwei Zi . Palladium-catalyzed enantioselective [2σ + 2π] cycloadditions of vinyl-carbonyl-bicyclo[1.1.0]butanes with arylidenemalononitriles. Chinese Chemical Letters, 2026, 37(1): 111072-. doi: 10.1016/j.cclet.2025.111072

    19. [19]

      Baokang GengXiang ChuLi LiuLingling ZhangShuaishuai ZhangXiao WangShuyan SongHongjie Zhang . High-efficiency PdNi single-atom alloy catalyst toward cross-coupling reaction. Chinese Chemical Letters, 2024, 35(7): 108924-. doi: 10.1016/j.cclet.2023.108924

    20. [20]

      Lang GaoCen ZhouRui WangFeng LanBohang AnXiaozhou HuangXiao Zhang . Unveiling inverse vulcanized polymers as metal-free, visible-light-driven photocatalysts for cross-coupling reactions. Chinese Chemical Letters, 2024, 35(4): 108832-. doi: 10.1016/j.cclet.2023.108832

Metrics
  • PDF Downloads(12)
  • Abstract views(2869)
  • HTML views(182)

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