Citation: Yong Wang, Xinyi Cao, Jingfei Ji, Xiuling Cui, Chao Pi, Leyao Zhao, Yangjie Wu. Water and fluorinated alcohol mediated/promoted tandem insertion/aerobic oxidation/bisindolylation under metal-free conditions: Easy access to bis(indolyl)methanes[J]. Chinese Chemical Letters, ;2021, 32(5): 1696-1700. doi: 10.1016/j.cclet.2020.12.026 shu

Water and fluorinated alcohol mediated/promoted tandem insertion/aerobic oxidation/bisindolylation under metal-free conditions: Easy access to bis(indolyl)methanes

Yong Wang ^a ,
Xinyi Cao ^b ,
Jingfei Ji ^b ,
Xiuling Cui ^{a, *,} ,
Chao Pi ^a ,
Leyao Zhao ^b ,
Yangjie Wu ^{a, *,}

a.
Henan Key Laboratory of Chemical Biology and Organic Chemistry, Key Laboratory of Applied Chemistry of Henan Universities, Green Catalysis Center, and College of Chemistry, Zhengzhou University, Zhengzhou 450052, China
b.
International College, Zhengzhou University, Zhengzhou 450052, China

cuixl@zzu.edu.cn

wyj@zzu.edu.cn

Received Date: 29 September 2020
Revised Date: 14 December 2020
Accepted Date: 16 December 2020
Available Online: 20 December 2020

Figures(5)

A green tandem reaction, including insertion/aerobic oxidation/bisindolylation, starting from indoles and diazo compounds has been developed. The combination of water and fluorinated alcohol plays dual roles as solvent and promoter in this chemical transformation. Molecular oxygen in the air acts as an oxidant. 3, 3'-Bis(indolyl)methanes with quaternary carbon were produced under metal-free conditions. No any catalyst and additive were required. N₂ and water were released as sole by-products. Absence of water and fluorinated alcohol resulted in Wolff rearrangement product.
- Bis(indolyl)methanes,
- Diazo,
- Fluorinated alcohol,
- Indole,
- Water
1. [1]
  (a) T.R. Garbe, M. Kobayashi, N. Shimizu, et al., J. Nat. Prod. 63 (2000) 596-598;
  (b) M. Kobayashi, S. Aoki, K. Gato, et al., Chem. Pharm. Bull. 42 (1994) 2449-2451;
  (c) R. Veluri, I. Oka, I. Wagner-Döbler, H. Laatsch, J. Nat. Prod. 66 (2003) 1520-1523;
  (d) R. Bell, S. Carmeli, N. Sar, J. Nat. Prod. 57 (1994) 1587-1590.
2. [2]
  (a) C. Hong, G.L. Firestone, L.F. Bjeldanes, Biochem. Pharmacol. 63 (2002) 1085-1097;
  (b) T. Irie, K. Kubushiro, K. Suzuki, et al., Anticancer Res. 19 (1999) 3061-3066;
  (c) H.T. Le, C.M. Schaldach, G.L. Firestone, L.F. Bjeldanes, J. Biol. Chem. 278 (2003) 21136-21145;
  (d) A. Kamal, Y.V.V. Srikanth, M.N.A. Khan, T.B. Shaik, M. Ashraf, Bioorg. Med. Chem. Lett. 20 (2010) 5229-5231;
  (e) B.V. Subba Reddy, N. Rajeswari, M. Sarangapani, et al., Bioorg. Med. Chem. Lett. 22 (2012) 2460-2463;
  (f) M. Shiri, M.A. Zolfigol, H.G. Kruger, Z. Tanbakouchian, Chem. Rev. 110 (2010) 2250-2293.
3. [3]
  (a) G. Gao, Y. Han, Z.H. Zhang, ChemistrySelect 2 (2017) 11561-11564;
  (b) J. Xiao, H. Wen, L. Wang, et al., Green Chem. 18 (2016) 1032-1037.
4. [4]
  (a) K. Fuji, Chem. Rev. 93 (1993) 2037-2066;
  (b) I. Denissova, L. Barriault, Tetrahedron 59 (2003) 10105-10146;
  (c) K.W. Quasdorf, L.E. Overman, Nature 516 (2014) 181-191;
  (d) R. Long, J. Huang, J. Gong, Z. Yang, Nat. Prod. Rep. 32 (2015) 1584-1601;
  (e) X.P. Zeng, Z.Y. Cao, Y.H. Wang, F. Zhou, J. Zhou, Chem. Rev. 116 (2016) 7330-7396;
  (f) J. Feng, M. Holmes, M.J. Krische, Chem. Rev. 117 (2017) 12564-12580;
  (g) Y. Li, S. Xu, Chem. Eur. J. 24 (2018) 16218-16245;
  (h) C. Li, S.S. Ragab, G. Liu, W. Tang, Nat. Prod. Rep. 37 (2020) 276-292.
5. [5]
  (a) M. Delgado-Rebollo, A. Prieto, P.J. Pérez, ChemCatChem 6 (2014) 2047-2052;
  (b) M.B. Johansen, M.A. Kerr, Org. Lett. 12 (2010) 4956-4959;
  (c) A. DeAngelis, V.W. Shurtleff, O. Dmitrenko, J.M. Fox, J. Am. Chem. Soc. 133 (2011) 1650-1653;
  (d) X. Gao, B. Wu, W.X. Huang, M.W. Chen, Y.G. Zhou, Angew. Chem. Int. Ed. 54 (2015) 11956-11960;
  (e) V. Arredondo, S.C. Hiew, E.S. Gutman, I.D.U.A. Premachandra, D.L. Van Vranken, Angew. Chem. Int. Ed. 56 (2017) 4156-4159.
6. [6]
  Z. Du, Y. Xing, P. Lu, Y. Wang, Org. Lett. 17(2015) 1192-1195. doi: 10.1021/acs.orglett.5b00089
7. [7]
  R.R. Singh, R.S. Liu, Chem. Commun. 53(2017) 4593-4596. doi: 10.1039/C7CC01304C
8. [8]
  X. Hu, F. Chen, Y. Deng, H. Jiang, W. Zeng, Org. Lett. 20(2018) 6140-6143. doi: 10.1021/acs.orglett.8b02613
9. [9]
  (a) C.J. Li, Chem. Rev. 105 (2005) 3095-3166;
  (b) C.J. Li, L. Chen, Chem. Soc. Rev. 35 (2006) 68-82;
  (c) A. Chanda, V.V. Fokin, Chem. Rev. 109 (2009) 725-748;
  (d) R.N. Butler, A.G. Coyne, Chem. Rev. 110 (2010) 6302-6337;
  (e) M.B. Gawande, V.D.B. Bonifácio, R. Luque, P.S. Branco, R.S. Varma, Chem. Soc. Rev. 42 (2013) 5522-5551.
10. [10]
  (a) R. Breslow, Acc. Chem. Res. 24 (1991) 159-164;
  (b) R. Breslow, Acc. Chem. Res. 37 (2004) 471-478;
  (c) S. Narayan, J. Muldoon, M.G. Finn, et al., Angew. Chem. Int. Ed. 44 (2005) 3275-3279;
  (d) W. Li, G. Yin, L. Huang, et al., Green Chem. 18 (2016) 4879-4883;
  (e) C. Wu, X. Xin, Z.M. Fu, et al., Green Chem. 19 (2017) 1983-1989;
  (f) S. Peng, Y.X. Song, J.Y. He, et al., Chin. Chem. Lett. 30 (2019) 2287-2290;
  (g) Y. Kim, C.J. Li, Green Synth. Catal. 1 (2020) 1-11.
11. [11]
  (a) J.P. Bégué, D. Bonnet-Delpon, B. Crousse, Synlett (2004) 18-29;
  (b) I.A. Shuklov, N.V. Dubrovina, A. Börner, Synthesis (2007) 2925-2943;
  (c) I. Colomer, A.E.R. Chamberlain, M.B. Haughey, T.J. Donohoe, Nat. Rev. Chem. 1 (2017) 0088;
  (d) J. Wencel-Delord, F. Colobert, Org. Chem. Front. 3 (2016) 394-400.
12. [12]
  (a) H.F. Motiwala, R.H. Vekariya, J. Aubé, Org. Lett. 17 (2015) 5484-5487;
  (b) R.H. Vekariya, J. Aubé, Org. Lett. 18 (2016) 3534-3537;
  (c) G.X. Li, J. Qu, Chem. Commun. 46 (2010) 2653-2655;
  (d) M. De Rosa, A. Soriente, Eur. J. Org. Chem. (2010) 1029-1032;
  (e) Z. Sadiq, M. Iqbal, E.A. Hussain, S. Naz, J. Mol. Liq. 255 (2018) 26-42;
  (f) W.C. Shiyao Lu, Qilong Shen, Chin. Chem. Lett. 30 (2019) 2279-2281.
13. [13]
  M.B. Rubin, R. Gleiter, Chem. Rev. 100(2000) 1121-1164. doi: 10.1021/cr960079j
14. [14]
  A. Saba, Synth. Commun. 24(1994) 695-699. doi: 10.1080/00397919408012648
15. [15]
  Y. Yu, Q. Sha, H. Cui, K.S. Chandler, M.P. Doyle, Org. Lett. 20(2018) 776-779. doi: 10.1021/acs.orglett.7b03912
16. [16]
  (a) R.D.C. Gallo, A.C.B. Burtoloso, Green Chem. 20 (2018) 4547-4556;
  (b) H.H. San, S.J. Wang, M. Jiang, X.Y. Tang, Org. Lett. 20 (2018) 4672-4676.
17. [17]
  (a) S.F. Zhu, C. Chen, Y. Cai, Q.L. Zhou, Angew. Chem. Int. Ed. 47 (2008) 932-934;
  (b) S.F. Zhu, Y. Cai, H.X. Mao, J.H. Xie, Q.L. Zhou, Nat. Chem. 2 (2010) 546-551.
18. [18]
  X.J. Lv, Y.H. Chen, Y.K. Liu, Org. Lett. 21(2019) 190-195. doi: 10.1021/acs.orglett.8b03654
19. [19]
  B.M. Trost, S. Malhotra, P. Koschker, P. Ellerbrock, J. Am. Chem. Soc. 134(2012) 2075-2084. doi: 10.1021/ja206995s
20. [20]
  (a) D. Vuluga, J. Legros, B. Crousse, et al., J. Org. Chem. 76 (2011) 1126-1133;
  (b) S. Khaksar, S.M. Vahdat, M. Gholizadeh, S.M. Talesh, J. Fluorine Chem. 136 (2012) 8-11;
  (c) C. Pi, X. Yin, X. Cui, Y. Ma, Y. Wu, Org. Lett. 21 (2019) 2081-2084.
1. [1]
  Haoyu Tian , Xiaolin Cui , Guiwei Yao , Wenyan Wei , Junchao Lu , Senyao Zheng , Xingjian Wang , Xun Chen , Guangkuan Zhao , Dulin Kong . The sulfenylation of enamine esters with heterocyclic thiols or disulfides in water and application to DNA-compatible chemistry. Chinese Chemical Letters, 2025, 36(12): 111006-. doi: 10.1016/j.cclet.2025.111006
2. [2]
  Yunhao Zhang , Yinuo Wang , Siran Wang , Dazhen Xu . Progress in Selective Construction of Functional Aromatics from Nitrogenous Cycloalkanes. University Chemistry, 2024, 39(11): 136-145. doi: 10.3866/PKU.DXHX202401083
3. [3]
  Shule Liu . Application of SPC/E Water Model in Molecular Dynamics Teaching Experiments. University Chemistry, 2024, 39(4): 338-342. doi: 10.3866/PKU.DXHX202310029
4. [4]
  Yanhui Zhong , Ran Wang , Zian Lin . Analysis of Halogenated Quinone Compounds in Environmental Water by Dispersive Solid-Phase Extraction with Liquid Chromatography-Triple Quadrupole Mass Spectrometry. University Chemistry, 2024, 39(11): 296-303. doi: 10.12461/PKU.DXHX202402017
5. [5]
  Ping Sun , Yuanqin Huang , Shunhong Chen , Xining Ma , Zhaokai Yang , Jian Wu . Indole derivatives as agrochemicals: An overview. Chinese Chemical Letters, 2024, 35(7): 109005-. doi: 10.1016/j.cclet.2023.109005
6. [6]
  Jingxiong Jiang , Yao Dong , Yuchun Wang , Lijuan Qi , Zhen-Yu Li , Tai-Bao Wei , Wen-Juan Qu , Qi Lin , Bingbing Shi . Separation of toluene-alcohol azeotropes by porous crystals of fluorinated leaning pillar[6]arene. Chinese Chemical Letters, 2025, 36(8): 110759-. doi: 10.1016/j.cclet.2024.110759
7. [7]
  Xuan Pan , Tao Sheng , Zhanzhu Liu . A concise total synthesis of monoterpenoid indole alkaloid (-)-voacafricine A. Chinese Chemical Letters, 2025, 36(10): 110913-. doi: 10.1016/j.cclet.2025.110913
8. [8]
  Cui Xin , Zi-Jian Zhao , Wei-Min He . Indole-quinoline transmutation enabled by a formal rhodium carbynoid. Chinese Chemical Letters, 2025, 36(11): 111583-. doi: 10.1016/j.cclet.2025.111583
9. [9]
  Yan-Li Li , Zhi-Ming Li , Kai-Kai Wang , Xiao-Long He . Beyond 1,4-addition of in-situ generated (aza-)quinone methides and indole imine methides. Chinese Chemical Letters, 2024, 35(7): 109322-. doi: 10.1016/j.cclet.2023.109322
10. [10]
  Wei Zhou , Xi Chen , Lin Lu , Xian-Rong Song , Mu-Jia Luo , Qiang Xiao . Recent advances in electrocatalytic generation of indole-derived radical cations and their applications in organic synthesis. Chinese Chemical Letters, 2024, 35(4): 108902-. doi: 10.1016/j.cclet.2023.108902
11. [11]
  Fang-Yuan Chen , Wen-Chao Geng , Kang Cai , Dong-Sheng Guo . Molecular recognition of cyclophanes in water. Chinese Chemical Letters, 2024, 35(5): 109161-. doi: 10.1016/j.cclet.2023.109161
12. [12]
  Kun Tang , Yu-Wu Zhong . Water reduction by an organic single-chromophore photocatalyst. Chinese Journal of Structural Chemistry, 2024, 43(8): 100376-100376. doi: 10.1016/j.cjsc.2024.100376
13. [13]
  Yan Zou , Yuting Xue , Chenxue Du , Wenyang Fu , Bin Xia , Yu He , Liang Ao , Xiaoshu Lv , Guangming Jiang . Anhydrous sodium sulfate microparticles for efficient water separation from surfactant-stabilized water-in-oil emulsions. Chinese Chemical Letters, 2025, 36(11): 110814-. doi: 10.1016/j.cclet.2025.110814
14. [14]
  Manman Ou , Yunjian Zhu , Jiahao Liu , Zhaoxuan Liu , Jianjun Wang , Jun Sun , Chuanxiang Qin , Lixing Dai . Polyvinyl alcohol fiber with enhanced strength and modulus and intense cyan fluorescence based on covalently functionalized graphene quantum dots. Chinese Chemical Letters, 2025, 36(2): 110510-. doi: 10.1016/j.cclet.2024.110510
15. [15]
  Yufeng ZHANG , Haotian QI , Jingya ZHONG , Leiming LANG , Guojun YUAN , Siqi LU , Haiying WANG , Guangxiang LIU . S-anion effects on the improvement of adsorption capacity and performance for benzyl alcohol electro-oxidation catalysts. Chinese Journal of Inorganic Chemistry, 2025, 41(12): 2591-2600. doi: 10.11862/CJIC.20250282
16. [16]
  Yi Zhang , Biao Wang , Chao Hu , Muhammad Humayun , Yaping Huang , Yulin Cao , Mosaad Negem , Yigang Ding , Chundong Wang . Fe–Ni–F electrocatalyst for enhancing reaction kinetics of water oxidation. Chinese Journal of Structural Chemistry, 2024, 43(2): 100243-100243. doi: 10.1016/j.cjsc.2024.100243
17. [17]
  Yang Yang , Jing-Li Luo , Xian-Zhu Fu . Water-oxidation intermediates enabling electrochemical propylene epoxidation. Chinese Journal of Structural Chemistry, 2024, 43(5): 100269-100269. doi: 10.1016/j.cjsc.2024.100269
18. [18]
  Jinjie Lu , Qikai Liu , Yuting Zhang , Yi Zhou , Yanbo Zhou . Antibacterial performance of cationic quaternary phosphonium-modified chitosan polymer in water. Chinese Chemical Letters, 2024, 35(9): 109406-. doi: 10.1016/j.cclet.2023.109406
19. [19]
  Wenhao Chen , Jian Du , Hanbin Zhang , Hancheng Wang , Kaicheng Xu , Zhujun Gao , Jiaming Tong , Jin Wang , Junjun Xue , Ting Zhi , Longlu Wang . Surface treatment of GaN nanowires for enhanced photoelectrochemical water-splitting. Chinese Chemical Letters, 2024, 35(9): 109168-. doi: 10.1016/j.cclet.2023.109168
20. [20]
  Shuyuan Pan , Zehui Yang , Fang Luo . Ni-based electrocatalysts for urea assisted water splitting. Chinese Journal of Structural Chemistry, 2024, 43(8): 100373-100373. doi: 10.1016/j.cjsc.2024.100373

Get Citation

PDF

XML

Metrics

PDF Downloads(12)
Abstract views(1584)
HTML views(107)

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