Citation: Ya-Shuai Liu, Yan Liu, Xiao-Wei Ma, Ping Liu, Jian-Wei Xie, Bin Dai. 3-(Diphenylphosphino)propanoic acid：An efficient ligand for the Cu-catalyzed N-arylation of imidazoles and 1H-pyrazole with aryl halides[J]. Chinese Chemical Letters, ;2014, 25(05): 775-778. doi: 10.1016/j.cclet.2014.01.042 shu

3-(Diphenylphosphino)propanoic acid：An efficient ligand for the Cu-catalyzed N-arylation of imidazoles and 1H-pyrazole with aryl halides

1.
School of Chemistry and Chemical Engineering/Key Laboratory for Green Processing of Chemical Engineering of Xinjiang Bingtuan, Shihezi University, Shihezi 832003, China

Corresponding author: Ping Liu,
Received Date: 27 November 2013
Available Online: 16 January 2014
Fund Project: We gratefully acknowledge financial support of this work by the National Basic Research Program of China (973 Program, No. 2012CB722603) (973 Program, No. 2012CB722603) the National Natural Science Foundation of China (No. 21103114) (No. IRT1161) and the Doctor Foundation of Xinjiang Bingtuan (No. 2012BB010). (No. 21103114)

3-(Diphenylphosphino)propanoic acid (L2) has proved to be an efficient ligand for the copper-catalyzed C-N coupling reactions. N-arylation of imidazoles with aryl iodides catalyzed by CuCl/L2 was smoothly carried out in DMSO at 100 ℃ with a yield up to 98%. N-arylation of 1H-pyrazole with aryl iodides and bromides catalyzed by Cu(OAc)₂/L2 in 1,4-dioxane also gave the corresponding products with yields of 40%-98%.
- Cu catalyzed,
- C-N coupling,
- N-arylation,
- P,O ligands
1. [1]
  [1] N.R. Candeias, L.C. Branco, P.M. Gois, C.A.M. Afonso, A.F. Trindade, More sustainable approaches for the synthesis of N-based heterocycles, Chem. Rev. 109 (2009) 2703-2802.
2. [2]
  [2] J.F. Hartwig, Palladium-catalyzed amination of aryl halides and sulfonates, in: A. Ricci (Ed.),Modern AminationMethods, Wiley-VCH,Weinheim, 2000, pp. 195-262.
3. [3]
  [3] (a) J.P. Wolfe, S.L. Buchwald, Nickel-catalyzed amination of aryl chlorides, J. Am. Chem. Soc. 119 (1997) 6054-6058; (b) C. Desmarets, R. Schneider, Y. Fort, Nickel(0)/dihydroimidazol-2-ylidene complex catalyzed coupling of aryl chlorides and amines, J. Org. Chem. 67 (2002) 3029-3036; (c) S. Tasler, B.H. Lipshutz, Nickel-on-charcoal-catalyzed aromatic aminations and Kumada couplings: mechanistic and synthetic aspects, J. Org. Chem. 68 (2003) 1190-1199.
4. [4]
  [4] (a) F. Monnier, M. Taillefer, Catalytic C-C, C-N and C-O Ullmann-type coupling reactions, Angew. Chem. Int. Ed. 48 (2009) 6954-6971; (b) M.G. Boswell, F.G. Yeung, C. Wolf, Copper-catalyzed C-N bond formation with N-heterocycles and aryl halides, Synlett 23 (2012) 1240-1244; (c) Y.C. Teo, F.F. Yong, G.S. Lim, A manganese/copper bimetallic catalyst for C-N coupling reactions under mild conditions in water, Tetrahedron Lett. 52 (2011) 7171-7174.
5. [5]
  [5] (a) R.K. Gujadhur, D. Venkataraman, J.T. Kintigh, Formation of aryl-nitrogen bonds using a soluble copper(I) catalyst, Tetrahedron Lett. 42 (2001) 4791-4793; (b) R.K. Gujadhur, C.G. Bates, D. Venkataraman, Formation of aryl-nitrogen, aryloxygen, and aryl-carbon bonds using well-defined copper(I)-based catalysts, Org. Lett. 3 (2001) 4315-4317.
6. [6]
  [6] M.H. Yang, F. Liu, An Ullmann coupling of aryl iodides and amines using an airstable diazaphospholane ligand, J. Org. Chem. 72 (2007) 8969-8971.
7. [7]
  [7] (a) A. Kiyomori, J.F.Marcoux, S.L. Buchwald, An efficient copper-catalyzed coupling of aryl halides with imidazoles, Tetrahedron Lett. 40 (1999) 2657-2660; (b) L.B. Liu,M. Frohn, N. Xi, et al., A soluble base for the copper-catalyzed imidazole N-arylations with aryl halides, J. Org. Chem. 70 (2005) 10135-10138; (c) A.A. Kelkar, N.M. Patil, R.V. Chaudhari, Copper-catalyzed amination of aryl halides: single-step synthesis of triarylamines, Tetrahedron Lett. 43 (2002) 7143-7146; (d) Y.H. Liu, C. Chen, L.M. Yang, Diazabutadiene: a simple and efficient ligand for copper-catalyzed N-arylation of aromatic amines, Tetrahedron Lett. 47 (2006) 9275-9278.
8. [8]
  [8] (a) J.C. Antilla, A. Klapars, S.L. Buchwald, The copper-catalyzed N-arylation of indoles, J. Am. Chem. Soc. 124 (2002) 11684-11688; (b) A. Klapars, X.H. Huang, S.L. Buchwald, A general and efficient copper catalyst for the amidation of aryl halides, J. Am. Chem. Soc. 124 (2002) 7421-7428; (c) B. Mallesham, B.M. Rajesh, P.R. Reddy, D. Srinivas, S. Trehan, Highly efficient CuI-catalyzed coupling of aryl bromides with oxazolidinones using Buchwald's protocol: a short route to Linezolid and Toloxatone, Org. Lett. 5 (2003) 963-965; (d) P.S. Wang, C.K. Liang, M.K. Leung, An improved Ullmann-Ukita-Buchwald-Li conditions for CuI-catalyzed coupling reaction of 2-pyridones with aryl halides, Tetrahedron 61 (2005) 2931-2939; (e) E. Alcalde, I. Dinares, S. Rodríguez, C.G. de Miguel, Synthetic approaches to sterically hindered n-arylimidazoles through copper-catalyzed coupling reactions, Eur. J. Org. Chem. (2005) 1637-1643; (f) P.E. Maligres, S.W. Krska, P.G. Dormer, A soluble copper(I) source and stable salts of volatile ligands for copper-catalyzed C-X couplings, J. Org. Chem. 77 (2012) 7646-7651.
9. [9]
  [9] F.Y. Kwong, A. Klapars, S.L. Buchwald, Copper-catalyzed coupling of alkylamines and aryl iodides: an efficient system even in an air atmosphere, Org. Lett. 4 (2002) 581-584.
10. [10]
  [10] Y.J. Chen, H.H. Chen, 1,1,1-Tris(hydroxymethyl)ethane as a new, efficient, and versatile tripod ligand for copper-catalyzed cross-coupling reactions of aryl iodides with amides, thiols, and phenols, Org. Lett. 8 (2006) 5609-5612.
11. [11]
  [11] D.S. Jiang, H. Fu, Y.Y. Jiang, Y.F. Zhao, CuBr/rac-BINOL-catalyzed N-arylations of aliphatic amines at room temperature, J. Org. Chem. 72 (2007) 672-674.
12. [12]
  [12] F.Y. Kwong, S.L. Buchwald, Mild and efficient copper-catalyzed amination of aryl bromides with primary alkylamines, Org. Lett. 5 (2003) 793-796.
13. [13]
  [13] (a) A. Shafir, S.L. Buchwald, Highly selective room temperature copper-catalyzed C-N coupling reactions, J. Am. Chem. Soc. 128 (2006) 8742-8743; (b) Z.X. Xi, F.H. Liu, Y.B. Zhou, W.Z. Chen, CuI/L (L = pyridine-functionalized 1,3- diketones) catalyzed C-N coupling reactions of aryl halides with NH-containing heterocycles, Tetrahedron 64 (2008) 4254-4259; (c) X.H. Zhu, L. Su, L.Y. Huang, et al., A facile and efficient oxalyldihydrazide/ ketone-promoted copper-catalyzed amination of aryl halides in water, Eur. J. Org. Chem. (2009) 635-642.
14. [14]
  [14] X. Lv, W.L. Bao, A b-keto ester as a novel, efficient, and versatile ligand for copper(I)-catalyzed C-N, C-O, and C-S coupling reactions, J. Org. Chem. 72 (2007) 3863-3867.
15. [15]
  [15] (a) H.J. Cristau, P.P. Cellier, J.F. Spindler, M. Taillefer, Highly efficient and mild copper-catalyzed N- and C-arylations with aryl bromides and iodides, Chem. Eur. J. 10 (2004) 5607-5622; (b) Z.Q. Wu, Z.Q. Jiang, D. Wu, H.F. Xiang, X.G. Zhou, A simple and efficient catalytic system for coupling aryl halides with aqueous ammonia in water, Eur. J. Org. Chem. (2010) 1854-1857; (c) Z.Q. Wu, L. Zhou, Z.Q. Jiang, et al., Sulfonato-Cu(salen) complex catalyzed Narylation of aliphatic amines with aryl halides in water, Eur. J. Org. Chem. (2010) 4971-4975; (d) Y. Wang, Z.Q. Wu, L.X. Wang, Z.K. Li, X.G. Zhou, A simple and efficient catalytic system for N-arylation of imidazoles in water, Chem. Eur. J. 15 (2009) 8971-8974.
16. [16]
  [16] (a) D.W. Ma, Q. Cai, H. Zhang, Mild method for Ullmann coupling reaction of amines and aryl halides, Org. Lett. 5 (2003) 2453-2455; (b) D.W. Ma, Q. Cai, L-Proline promoted Ullmann-type coupling reactions of aryl iodides with indoles, pyrroles, imidazoles or pyrazoles, Synlett (2004) 128-130; (c) Q. Cai, H. Zhang, W. Zhu, Y.D. Zhang, D.W. Ma, Preparation of N-aryl compounds by amino acid-promoted Ullmann-type coupling reactions, Synthesis (2005) 496-499; (d) H. Zhang, Q. Cai, D.W. Ma, Amino acid promoted CuI-catalyzed C-N bond formation between aryl halides and amines or N-containing heterocycles, J. Org. Chem. 70 (2005) 5164-5173; (e) X. Lv, Z.M. Wang, W.L. Bao, CuI catalyzed C-N bond forming reactions between aryl/heteroaryl bromides and imidazoles in [Bmim]BF4, Tetrahedron 62 (2006) 4756-4761.
17. [17]
  [17] (a) Z.K. Lu, R.J. Twieg, S.D. Huang, Copper-catalyzed amination of aromatic halides with 2-n,n-dimethylaminoethanol as solvent, Tetrahedron Lett. 44 (2003) 6289-6292; (b) Z.K. Lu, R.J. Twieg, Copper-catalyzed aryl amination in aqueous media with 2- dimethylaminoethanol ligand, Tetrahedron Lett. 46 (2005) 2997-3001.
18. [18]
  [18] H.H. Rao, H. Fu, Y.Y. Jiang, Y.F. Zhao, Copper-catalyzed arylation of amines using diphenyl pyrrolidine-2-phosphonate as the new ligand, J. Org. Chem. 70 (2005) 8107-8109.
19. [19]
  [19] W. Keim, Vor- und Nachteile der homogeneU¨ bergangs metallkatalyse, dargestellt am SHOP-Prozeb, Chem. Ing. Tech. 56 (1984) 850-853.
20. [20]
  [20] (a) A. Bader, E. Lindner, Coordination chemistry and catalysis with hemilabile oxygen-phosphorus ligands, Coord. Chem. Rev. 108 (1991) 27-110; (b) G.J.P. Britovsek, W. Keim, S. Mecking, D. Sainzb, T. Wagner, Hemilabile P,Oligands in palladium catalysed C-C linkages: codimerization of ethylene and styrene and cooligomerization of ethylene and carbon monoxide, J. Chem. Soc. Chem. Commun. (1993) 1632-1634.
21. [21]
  [21] (a) X. Du, X.J. Feng, Y. Liu, R. He, M. Bao, Suzuki reaction of bromoallenes with arylboronic acids using an air-stable palladium complex Pd(Ph2PCH2CO2)2 as a precatalyst, Chin. Chem. Lett. 21 (2010) 641-644; (b) L. Zhou, Q.Q. Miao, R. He, X.J. Feng, M. Bao, Ni-catalyzed cross-coupling reaction of aryl chlorides with arylboronic acids in IPA without using a reducing reagent, Tetrahedron Lett. 48 (2007) 7899-7902.
22. [22]
  [22] (a) M.P. Guo, F.F. Jian, R. He, Efficient synthesis of fluorinated biphenyl derivatives via Pd-catalyzed Suzuki coupling reactions in aqueous solvents at room temperature, J. Fluorine Chem. 27 (2006) 177-181; (b) M.P. Guo, F.F. Jian, R. He, Cross coupling reactions catalyzed by P,O chelate palladium complexes at room temperature, Tetrahedron Lett. 46 (2005) 9017- 9020.
23. [23]
  [23] E. Ullah, J. McNulty, A. Robertson, A novel P,O-type phosphorinane ligand for the Suzuki-Miyaura cross-coupling of aryl chlorides, Tetrahedron Lett. 50 (2009) 5599-5601.
24. [24]
  [24] (a) F.T. Wu, P. Liu, X.W. Ma, J.W. Xie, B. Dai, Tetrazole-1-acetic acid as a ligand for copper-catalyzed N-arylation of imidazoles with aryl iodides under mild conditions, Chin. J. Chem. 24 (2013) 893-896; (b) Y.L. Jiao, N.N. Yan, J.W. Xie, et al., A simple and efficient copper(II) complex as a catalyst for N-arylation of imidazoles, Chin. J. Chem. 31 (2013) 267-270; (c) Y. Liu, Q. Zhang, X.W. Ma, et al., Salen-Cu(II) complex catalyzed N-arylation of imidazoles under mild conditions, Inter. J. Org. Chem. 3 (2013) 185-189; (d) Y. Liu, W. Liu, Q. Zhang, et al., Salen-Cu(II) complex catalyzed N-arylation of pyrazole under mild conditions, J. Chem. Res. (2013) 636-637.
25. [25]
  [25] (a) K. Issleib, G. Thomas, Basizitäts, IR und NMR untersuchungen an carboxyalkylphosphinen und deren derivaten, Z. Anorg. Allg. Chem. 330 (1964) 295- 308; (b) K. Issleib, G. Thomas, Alkali-Phosphorverbindungen und ihr reaktives Verhalten, V. Darstellung von Carboxyphosphinen R₂P-[CH₂]_n-CO₂H, Chem. Ber. 93 (1960) 803-808.
1. [1]
  Yue Zhang , Xiaoya Fan , Xun He , Tingyu Yan , Yongchao Yao , Dongdong Zheng , Jingxiang Zhao , Qinghai Cai , Qian Liu , Luming Li , Wei Chu , Shengjun Sun , Xuping Sun . Ambient electrosynthesis of urea from carbon dioxide and nitrate over Mo₂C nanosheet. Chinese Chemical Letters, 2024, 35(8): 109806-. doi: 10.1016/j.cclet.2024.109806
2. [2]
  Shengkai Li , Yuqin Zou , Chen Chen , Shuangyin Wang , Zhao-Qing Liu . Defect engineered electrocatalysts for C–N coupling reactions toward urea synthesis. Chinese Chemical Letters, 2024, 35(8): 109147-. doi: 10.1016/j.cclet.2023.109147
3. [3]
  Kaihui Huang , Boning Feng , Xinghua Wen , Lei Hao , Difa Xu , Guijie Liang , Rongchen Shen , Xin Li . Effective photocatalytic hydrogen evolution by Ti3C2-modified CdS synergized with N-doped C-coated Cu2O in S-scheme heterojunctions. Chinese Journal of Structural Chemistry, 2023, 42(12): 100204-100204. doi: 10.1016/j.cjsc.2023.100204
4. [4]
  Qinyu Zhao , Yunchao Zhao , Songjing Zhong , Zhaoyang Yue , Zhuoheng Jiang , Shaobo Wang , Quanhong Hu , Shuncheng Yao , Kaikai Wen , Linlin Li . Urchin-like piezoelectric ZnSnO₃/Cu₃P p-n heterojunction for enhanced cancer sonodynamic therapy. Chinese Chemical Letters, 2024, 35(12): 109644-. doi: 10.1016/j.cclet.2024.109644
5. [5]
  Bowen Wang , Longwu Sun , Qianqian Cao , Xinzhi Li , Jianai Chen , Shizhao Wang , Miaolin Ke , Fener Chen . Cu-catalyzed three-component CSP coupling for the synthesis of trisubstituted allenyl phosphorothioates. Chinese Chemical Letters, 2024, 35(12): 109617-. doi: 10.1016/j.cclet.2024.109617
6. [6]
  Hong-Tao Ji , Yu-Han Lu , Yan-Ting Liu , Yu-Lin Huang , Jiang-Feng Tian , Feng Liu , Yan-Yan Zeng , Hai-Yan Yang , Yong-Hong Zhang , Wei-Min He . Nd@C₃N₄-photoredox/chlorine dual catalyzed synthesis and evaluation of antitumor activities of 4-alkylated sulfonyl ketimines. Chinese Chemical Letters, 2025, 36(2): 110568-. doi: 10.1016/j.cclet.2024.110568
7. [7]
  Entian Cui , Yulian Lu , Zhaoxia Li , Zhilei Chen , Chengyan Ge , Jizhou Jiang . Interfacial B-O bonding modulated S-scheme B-doped N-deficient C₃N₄/O-doped-C₃N₅ for efficient photocatalytic overall water splitting. Chinese Chemical Letters, 2025, 36(1): 110288-. doi: 10.1016/j.cclet.2024.110288
8. [8]
  Yan-Bo Li , Yi Li , Liang Yin . Copper(Ⅰ)-catalyzed diastereodivergent construction of vicinal P-chiral and C-chiral centers facilitated by dual "soft-soft" interaction. Chinese Chemical Letters, 2024, 35(7): 109294-. doi: 10.1016/j.cclet.2023.109294
9. [9]
  Wei Zhong , Dan Zheng , Yuanxin Ou , Aiyun Meng , Yaorong Su . K原子掺杂高度面间结晶的g-C₃N₄光催化剂及其高效H₂O₂光合成. Acta Physico-Chimica Sinica, 2024, 40(11): 2406005-. doi: 10.3866/PKU.WHXB202406005
10. [10]
  Guoqiang Chen , Zixuan Zheng , Wei Zhong , Guohong Wang , Xinhe Wu . 熔融中间体运输导向合成富氨基g-C₃N₄纳米片用于高效光催化产H₂O₂. Acta Physico-Chimica Sinica, 2024, 40(11): 2406021-. doi: 10.3866/PKU.WHXB202406021
11. [11]
  Yan XU , Suzhi LI , Yan LI , Lushun FENG , Wentao SUN , Xinxing LI . Structure variation of cadmium naphthalene-diphosphonates with the changing rigidity of N-donor auxiliary ligands. Chinese Journal of Inorganic Chemistry, 2025, 41(2): 395-406. doi: 10.11862/CJIC.20240226
12. [12]
  Bin Chen , Chaoyang Zheng , Dehuan Shi , Yi Huang , Renxia Deng , Yang Wei , Zheyuan Liu , Yan Yu , Shenghong Zhong . p-d orbital hybridization induced by CuGa2 promotes selective N2 electroreduction. Chinese Journal of Structural Chemistry, 2025, 44(1): 100468-100468. doi: 10.1016/j.cjsc.2024.100468
13. [13]
  Yue Sun , Liming Yang , Yaohang Cheng , Guanghui An , Guangming Li . Pd(I)-catalyzed ring-opening arylation of cyclopropyl-α-aminoamides: Access to α-ketoamide peptidomimetics. Chinese Chemical Letters, 2024, 35(6): 109250-. doi: 10.1016/j.cclet.2023.109250
14. [14]
  Long TANG , Yaxin BIAN , Luyuan CHEN , Xiangyang HOU , Xiao WANG , Jijiang WANG . Syntheses, structures, and properties of three coordination polymers based on 5-ethylpyridine-2,3-dicarboxylic acid and N-containing ligands. Chinese Journal of Inorganic Chemistry, 2024, 40(10): 1975-1985. doi: 10.11862/CJIC.20240180
15. [15]
  Heng Chen , Longhui Nie , Kai Xu , Yiqiong Yang , Caihong Fang . 两步焙烧法制备大比表面积和结晶性增强超薄g-C₃N₄纳米片及其高效光催化产H₂O₂. Acta Physico-Chimica Sinica, 2024, 40(11): 2406019-. doi: 10.3866/PKU.WHXB202406019
16. [16]
  Qianqian Liu , Xing Du , Wanfei Li , Wei-Lin Dai , Bo Liu . Synergistic Effects of Internal Electric and Dipole Fields in SnNb₂O₆/Nitrogen-Enriched C₃N₅ S-Scheme Heterojunction for Boosting Photocatalytic Performance. Acta Physico-Chimica Sinica, 2024, 40(10): 2311016-. doi: 10.3866/PKU.WHXB202311016
17. [17]
  Hualin Jiang , Wenxi Ye , Huitao Zhen , Xubiao Luo , Vyacheslav Fominski , Long Ye , Pinghua Chen . Novel 3D-on-2D g-C₃N₄/AgI._x._y heterojunction photocatalyst for simultaneous and stoichiometric production of H₂ and H₂O₂ from water splitting under visible light. Chinese Chemical Letters, 2025, 36(2): 109984-. doi: 10.1016/j.cclet.2024.109984
18. [18]
  Xiaoxiao Huang , Zhi-Long He , Yangpeng Chen , Lei Li , Zhenyu Yang , Chunyang Zhai , Mingshan Zhu . Novel P-doping-tuned Pd nanoflowers/S,N-GQDs photo-electrocatalyst for high-efficient ethylene glycol oxidation. Chinese Chemical Letters, 2024, 35(6): 109271-. doi: 10.1016/j.cclet.2023.109271
19. [19]
  Weichen Zhu , Wei Zuo , Pu Wang , Wei Zhan , Jun Zhang , Lipin Li , Yu Tian , Hong Qi , Rui Huang . Fe-N-C heterogeneous Fenton-like catalyst for the degradation of tetracycline: Fe-N coordination and mechanism studies. Chinese Chemical Letters, 2024, 35(9): 109341-. doi: 10.1016/j.cclet.2023.109341
20. [20]
  Liangfeng Yang , Liang Zeng , Yanping Zhu , Qiuan Wang , Jinheng Li . Copper-catalyzed photoredox 1,4-amidocyanation of 1,3-enynes with N-amidopyridin-1-ium salts and TMSCN: Facile access to α-amido allenyl nitriles. Chinese Chemical Letters, 2024, 35(11): 109685-. doi: 10.1016/j.cclet.2024.109685

Get Citation

PDF

XML

Metrics

PDF Downloads(0)
Abstract views(801)
HTML views(32)

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