注册 English

Copper-catalyzed N-arylation of 2-arylindoles with aryl halides

Wei Liu ,  Li-Ya Han ,  Rui-Li Liu ,  Li-Ge Xu ,  Yan-Lan Bi

downloadPDF
Citation:  Wei Liu, Li-Ya Han, Rui-Li Liu, Li-Ge Xu, Yan-Lan Bi. Copper-catalyzed N-arylation of 2-arylindoles with aryl halides[J]. Chinese Chemical Letters, 2014, 25(9): 1240-1243. doi: 10.1016/j.cclet.2014.04.021 shu

Copper-catalyzed N-arylation of 2-arylindoles with aryl halides

    • 通讯作者: Wei Liu,
  • 基金项目:

    This work was supported by the National Natural Science Foundation of China (No. 21102036)  (No. 21102036)

    Plan for Scientific Innovation Talent of Henan University of Technology (No. 11CXRC02)  (No. 11CXRC02)

    startup fund from HAUT (No. 2010BS042). (No. 2010BS042)

摘要: 10 mol% CuI combined with the DMEDA ligand can efficiently catalyze the N-arylation of 2-arylindoles with aryl iodides and aryl bromides in good to excellent yields. The aryl halides bearing electron-rich or electron-deficient functional groups can be well tolerated under this mild reaction conditions.

English

  • 

    1. [1] S.V. Ley, A.W. Thomas, Modern synthetic methods for copper-mediated C(aryl)-O, C(aryl)-N, and C(aryl)-S bond formation, Angew. Chem. Int. Ed. Engl. 42 (2003) 5400-5449.[1] S.V. Ley, A.W. Thomas, Modern synthetic methods for copper-mediated C(aryl)-O, C(aryl)-N, and C(aryl)-S bond formation, Angew. Chem. Int. Ed. Engl. 42 (2003) 5400-5449.

    2. [2] F. Monnier, M. Taillefer, Catalytic C-C, C-N, and C-O Ullmann-type coupling reactions: copper makes a difference, Angew. Chem. Int. Ed. Engl. 47 (2008) 3096-3099.[2] F. Monnier, M. Taillefer, Catalytic C-C, C-N, and C-O Ullmann-type coupling reactions: copper makes a difference, Angew. Chem. Int. Ed. Engl. 47 (2008) 3096-3099.

    3. [3] Y. Wang, J. Zeng, X. Cui, Recent progress in copper-catalyzed C-N coupling reactions, Chin. J. Org. Chem. 30 (2010) 181-199.[3] Y. Wang, J. Zeng, X. Cui, Recent progress in copper-catalyzed C-N coupling reactions, Chin. J. Org. Chem. 30 (2010) 181-199.

    4. [4] J.D. Senra, L.C.S. Aguiar, A.B.C. Simas, Recent progress in transition-metal catalyzed C-N cross-couplings: emerging approaches towards sustainability, Curr. Org. Synth. 8 (2011) 53-78.[4] J.D. Senra, L.C.S. Aguiar, A.B.C. Simas, Recent progress in transition-metal catalyzed C-N cross-couplings: emerging approaches towards sustainability, Curr. Org. Synth. 8 (2011) 53-78.

    5. [5] A. Klapars, J.C. Antilla, X. Huang, S.L. Buchwald, A general and efficient copper catalyst for the amidation of aryl halides and the N-arylation of nitrogen heterocycles, J. Am. Chem. Soc. 123 (2001) 7727-7729.[5] A. Klapars, J.C. Antilla, X. Huang, S.L. Buchwald, A general and efficient copper catalyst for the amidation of aryl halides and the N-arylation of nitrogen heterocycles, J. Am. Chem. Soc. 123 (2001) 7727-7729.

    6. [6] J.C. Antilla, A. Klapars, S.L. Buchwald, The copper-catalyzed N-arylation of indoles, J. Am. Chem. Soc. 124 (2002) 11684-11688.[6] J.C. Antilla, A. Klapars, S.L. Buchwald, The copper-catalyzed N-arylation of indoles, J. Am. Chem. Soc. 124 (2002) 11684-11688.

    7. [7] A. Klapars, X. Huang, S.L. Buchwald, A general and efficient copper catalyst for the amidation of aryl halides, J. Am. Chem. Soc. 124 (2002) 7421-7428.[7] A. Klapars, X. Huang, S.L. Buchwald, A general and efficient copper catalyst for the amidation of aryl halides, J. Am. Chem. Soc. 124 (2002) 7421-7428.

    8. [8] H. Cristau, P.P. Cellier, J. Spindler, M. Taillefer, Highly efficient and mild coppercatalyzed N-and C-arylations with aryl bromides and iodides, Chem. Eur. J. 10 (2004) 5607-5622.[8] H. Cristau, P.P. Cellier, J. Spindler, M. Taillefer, Highly efficient and mild coppercatalyzed N-and C-arylations with aryl bromides and iodides, Chem. Eur. J. 10 (2004) 5607-5622.

    9. [9] X. Diao, Y. Wang, Y. Jiang, D. Ma, Assembly of substituted 1H-benzimidazoles and 1,3-dihydrobenzimidazol-2-ones via CuI/L-proline catalyzed coupling of aqueous ammonia with 2-iodoacetanilides and 2-iodophenylcarbamates, J. Org. Chem. 74 (2009) 7974-7977.[9] X. Diao, Y. Wang, Y. Jiang, D. Ma, Assembly of substituted 1H-benzimidazoles and 1,3-dihydrobenzimidazol-2-ones via CuI/L-proline catalyzed coupling of aqueous ammonia with 2-iodoacetanilides and 2-iodophenylcarbamates, J. Org. Chem. 74 (2009) 7974-7977.

    10. [10] R.K. Rao, A.B. Naidu, E.A. Jaseer, G. Sekar, An efficient, mild, and selective Ullmanntype N-arylation of indoles catalyzed by copper(I) complex, Tetrahedron 65 (2009) 4619-4624.[10] R.K. Rao, A.B. Naidu, E.A. Jaseer, G. Sekar, An efficient, mild, and selective Ullmanntype N-arylation of indoles catalyzed by copper(I) complex, Tetrahedron 65 (2009) 4619-4624.

    11. [11] A.K. Verma, J. Singh, R.C. Larock, Benzotriazole: an efficient ligand for the copper-catalyzed N-arylation of indoles, Tetrahedron 65 (2009) 8434-8439.[11] A.K. Verma, J. Singh, R.C. Larock, Benzotriazole: an efficient ligand for the copper-catalyzed N-arylation of indoles, Tetrahedron 65 (2009) 8434-8439.

    12. [12] S. Haneda, Y. Adachi, M. Hayashi, Copper(I)-2-(20-pyridyl)benzimidazole catalyzed N-arylation of indoles, Tetrahedron 65 (2009) 10459-10462.[12] S. Haneda, Y. Adachi, M. Hayashi, Copper(I)-2-(20-pyridyl)benzimidazole catalyzed N-arylation of indoles, Tetrahedron 65 (2009) 10459-10462.

    13. [13] X. Yang, H. Xing, Y. Zhang, et al., CuI/8-hydroxyquinalidine promoted N-arylation of indole and azoles, Chin. J. Chem. 30 (2012) 875-880.[13] X. Yang, H. Xing, Y. Zhang, et al., CuI/8-hydroxyquinalidine promoted N-arylation of indole and azoles, Chin. J. Chem. 30 (2012) 875-880.

    14. [14] F. Wu, P. Liu, X. Ma, J. Xie, B. Dai, Tetrazole-1-acetic acid as a ligand for coppercatalyzed N-arylation of imidazoles with aryl iodides under mild conditions, Chin. Chem. Lett. 24 (2013) 893-896.[14] F. Wu, P. Liu, X. Ma, J. Xie, B. Dai, Tetrazole-1-acetic acid as a ligand for coppercatalyzed N-arylation of imidazoles with aryl iodides under mild conditions, Chin. Chem. Lett. 24 (2013) 893-896.

    15. [15] J. Engel-Andreasen, B. Shimpukade, T. Ulven, Selective copper catalysed aromatic N-arylation in water, Green Chem. 15 (2013) 336-340.[15] J. Engel-Andreasen, B. Shimpukade, T. Ulven, Selective copper catalysed aromatic N-arylation in water, Green Chem. 15 (2013) 336-340.

    16. [16] L.B. Zhu, L. Cheng, Y.X. Zhang, R.G. Xie, J.S. You, Highly efficient copper-catalyzed N-arylation of nitrogen-containing heterocycles with aryl and heteroaryl halides, J. Org. Chem. 72 (2007) 2737-2743.[16] L.B. Zhu, L. Cheng, Y.X. Zhang, R.G. Xie, J.S. You, Highly efficient copper-catalyzed N-arylation of nitrogen-containing heterocycles with aryl and heteroaryl halides, J. Org. Chem. 72 (2007) 2737-2743.

    17. [17] L.B. Zhu, G.C. Li, L. Luo, et al., Highly functional group tolerance in coppercatalyzed N-arylation of nitrogen-containing heterocycles under mild conditions, J. Org. Chem. 74 (2009) 2200-2202.[17] L.B. Zhu, G.C. Li, L. Luo, et al., Highly functional group tolerance in coppercatalyzed N-arylation of nitrogen-containing heterocycles under mild conditions, J. Org. Chem. 74 (2009) 2200-2202.

    18. [18] N. Panda, A.K. Jena, S. Mohapatra, S.R. Rout, Copper ferrite nanoparticle-mediated N-arylation of heterocycles: a ligand-free reaction, Tetrahedron Lett. 52 (2011) 1924-1927.[18] N. Panda, A.K. Jena, S. Mohapatra, S.R. Rout, Copper ferrite nanoparticle-mediated N-arylation of heterocycles: a ligand-free reaction, Tetrahedron Lett. 52 (2011) 1924-1927.

    19. [19] N.V. Suramwar, S.R. Thakare, N.N. Karade, N.T. Khaty, Green synthesis of predominant (1 1 1) facet CuO nanoparticles: heterogeneous and recyclable catalyst for N-arylation of indoles, J. Mol. Cat. A: Chem. 359 (2012) 28-34.[19] N.V. Suramwar, S.R. Thakare, N.N. Karade, N.T. Khaty, Green synthesis of predominant (1 1 1) facet CuO nanoparticles: heterogeneous and recyclable catalyst for N-arylation of indoles, J. Mol. Cat. A: Chem. 359 (2012) 28-34.

    20. [20] F.P. Yi, H.Y. Sun, X.H. Pan, Y. Xu, J.Z. Li, Synthesis of Fischer indole derivatives using carboxyl-functionalized ionic liquid as an efficient and recyclable catalyst, Chin. Chem. Lett. 20 (2009) 275-278.[20] F.P. Yi, H.Y. Sun, X.H. Pan, Y. Xu, J.Z. Li, Synthesis of Fischer indole derivatives using carboxyl-functionalized ionic liquid as an efficient and recyclable catalyst, Chin. Chem. Lett. 20 (2009) 275-278.

    21. [21] S.V. Goswami, P.B. Thorat, V.N. Kadam, S.A. Khiste, S.R. Bhusare, A convenient one-pot three component synthesis of 3-aminoalkylated indoles catalyzed by 3-chlorophenylboronic acid, Chin. Chem. Lett. 24 (2013) 422-424.[21] S.V. Goswami, P.B. Thorat, V.N. Kadam, S.A. Khiste, S.R. Bhusare, A convenient one-pot three component synthesis of 3-aminoalkylated indoles catalyzed by 3-chlorophenylboronic acid, Chin. Chem. Lett. 24 (2013) 422-424.

    22. [22] W.J. Smith III, J.S. Sawyer, A novel and selective method for the N-arylation of indoles mediated by KF/Al2O3, Tetrahedron Lett. 37 (1996) 299-302.[22] W.J. Smith III, J.S. Sawyer, A novel and selective method for the N-arylation of indoles mediated by KF/Al2O3, Tetrahedron Lett. 37 (1996) 299-302.

    23. [23] G.L. Frayne, G.M. Green, Investigation of the N-arylation of various substituted indoles using microwave-assisted technology, Tetrahedron Lett. 49 (2008) 7328-7329.[23] G.L. Frayne, G.M. Green, Investigation of the N-arylation of various substituted indoles using microwave-assisted technology, Tetrahedron Lett. 49 (2008) 7328-7329.

    24. [24] Z.W. Chen, N. Zhang, Z.H. Wang, W.K. Su, An efficient synthesis of novel chromeno[3'4':5,6]pyrano[2,3-b]indole derivatives, Chin. Chem. Lett. 24 (2013) 199-201.[24] Z.W. Chen, N. Zhang, Z.H. Wang, W.K. Su, An efficient synthesis of novel chromeno[3'4':5,6]pyrano[2,3-b]indole derivatives, Chin. Chem. Lett. 24 (2013) 199-201.

    25. [25] Y.X. Cui, L.D. Sun, Q. Sun, L. Shi, Highly selective synthesis of 3-methylindole from glycerol and aniline over Cu/NaY modified by K22O, Chin. Chem. Lett. 24 (2013) 1127-1129.[25] Y.X. Cui, L.D. Sun, Q. Sun, L. Shi, Highly selective synthesis of 3-methylindole from glycerol and aniline over Cu/NaY modified by K22O, Chin. Chem. Lett. 24 (2013) 1127-1129.

    26. [26] L. Ackermann, General and efficient indole syntheses based on catalytic amination reactions, Org. Lett. 7 (2005) 439-442.[26] L. Ackermann, General and efficient indole syntheses based on catalytic amination reactions, Org. Lett. 7 (2005) 439-442.

    27. [27] L.T. Kaspar, L. Ackermann, Three-component indole synthesis using ortho-dihaloarenes, Tetrahedron 61 (2005) 11311-11316.[27] L.T. Kaspar, L. Ackermann, Three-component indole synthesis using ortho-dihaloarenes, Tetrahedron 61 (2005) 11311-11316.

    28. [28] N.P. Bizier, J.W. Wackerly, E.D. Braunstein, et al., An alternative role for acetylenes: activation of fluorobenzenes toward nucleophilic aromatic substitution, J. Org. Chem. 78 (2013) 5987-5998.[28] N.P. Bizier, J.W. Wackerly, E.D. Braunstein, et al., An alternative role for acetylenes: activation of fluorobenzenes toward nucleophilic aromatic substitution, J. Org. Chem. 78 (2013) 5987-5998.

  • 加载中
WeChat 扫一扫看文章
计量
  • PDF下载量:  0
  • 文章访问数:  1633
  • HTML全文浏览量:  43
文章相关
  • 收稿日期:  2014-03-28
  • 网络出版日期:  2014-04-14
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

/

返回文章

All Rights Reserved by the Chinese Chemical Society   中国化学会 版权所有 京ICP备05002797号

本系统由北京仁和汇智信息技术有限公司开发    技术支持: info@rhhz.net