Citation: Wang Lili, Li Pengshuai, Jia Meilin, Bao Yongsheng. Aminolysis of Esters Using Quaternary Ammonium Salts as Amine Sources via Twice C-N Bond Activations[J]. Chinese Journal of Organic Chemistry, ;2017, 37(5): 1220-1230. doi: 10.6023/cjoc201612014 shu

Aminolysis of Esters Using Quaternary Ammonium Salts as Amine Sources via Twice C-N Bond Activations

  • Corresponding author: Bao Yongsheng, sbbys197812@163.com
  • Received Date: 6 December 2016
    Revised Date: 13 February 2017

    Fund Project: the Research Program of Science and Technology at University of Inner Mongolia Autonomous Region NJZZ14032the Initial Special Research for National Basic Research Program of China 2014CB460609by the National Natural Science Foundation of China 21462031

Figures(6)

  • Catalyzed by supported palladium nanoparticles, an aminolysis reaction between various aryl esters and quaternary ammonium salts via twice C-N bond activations has been developed for selectively synthesis of amides. The Pd/γ-Al2O3 catalyst exhibited an excellent catalytic activity and reusability of at least five recycles in air for the reaction. The experiment results indicated that the first C-N cleavage of quaternary ammonium salt affords the tertiary amine and halohydrocarbon, and the second C-N cleavage proceeds via the formation of an iminium intermediate.
  • 加载中
    1. [1]

      (a) Pattabiraman, V. R. ; Bode, J. W. Nature 2011, 480, 471. (b) Allen, C. L. ; Williams, J. M. J. Chem. Soc. Rev. 2011, 40, 3405. (c) Valeur, E. ; Bradley, M. Chem. Soc. Rev. 2009, 38, 606.

    2. [2]

      Bai, C. H.; Yao, X. F.; Li, Y. W. ACS Catal. 2015, 5, 884.  doi: 10.1021/cs501822r

    3. [3]

      (a) Nekkanti, S. ; Veeramani, K. ; Kumar, N. P. ; Shankaraiah, N. Green chem. 2016, 18, 3439. (b) Wu, K. ; Huang, Z. L. ; Ma, Y. Y. ; Lei, A. W. RSC Adv. 2016, 6, 24349.

    4. [4]

      Arefi, M.; Saberi, D.; Karimi, M.; Heydari, A. ACS Comb. Sci. 2015, 17, 341.  doi: 10.1021/co5001844

    5. [5]

      Ouyang, K.; Hao, W.; Zhang, W. X.; Xi, Z. Chem. Rev. 2015, 115, 12045.  doi: 10.1021/acs.chemrev.5b00386

    6. [6]

      (a) Bao, Y. S. ; Baiyin, M. ; Agula, B. ; Jia, M. L. ; Bao, Z. J. Org. Chem. 2014, 79, 6715. (b) Bao, Y. S. ; Bao, Z. ; Agula, B. ; Baiyin, M. ; Jia, M. L. J. Org. Chem. 2014, 79, 803.

    7. [7]

      (a) Li, Y. M. ; Jia, F. ; Li, Z. P. Chem. -Eur. J. 2012, 18, 5150. (b) Porcheddu, A. ; Luca, L. D. Adv. Synth. Catal. 2012, 354, 2949.

    8. [8]

      Xu, K.; Hu, Y. B.; Zhang, S.; Zha, Z. G.; Wang, Z. Y. Chem.-Eur. J. 2012, 18, 9793.  doi: 10.1002/chem.v18.32

    9. [9]

      Du, B.; Sun, P. Sci. China Chem. 2014, 57, 1176.

    10. [10]

      Gao, L.; Tang, H.; Wang, Z. Chem. Commun. 2014, 50, 4085.  doi: 10.1039/c4cc00621f

    11. [11]

      (a) Cassar, L. ; Foa, M. ; Gardano, A. J. Organomet. Chem. 1976, 121, C55. (b) Bhardwaj, M. ; Sahi, S. ; Mahajan, H. ; Paul, S. ; Clark, J. H. J. Mol. Catal. A: Chem. 2015, 408, 48. (c) Zhang, J. T. ; Li, D. Y. ; Chen, H. ; Wang, B. J. ; Liu, Z. X. ; Zhang, Y. H. Adv. Synth. Catal. 2016, 358, 792.

    12. [12]

      (a) Wang, X. ; Zhu, L. Z. ; Chen, S. H. ; Xu, X. H. ; Au, C. T. ; Qiu, R. Org. Lett. 2015, 17, 5228. (b) Lin, C. L. ; Li, D. ; Wang, Y. B. ; Yao, J. Z. ; Zhang, Y. H. Org. Lett. 2015, 17, 1328. (c) Fabrizi, G. ; Goggiamani, A. ; Sferrazza, A. ; Cacchi, S. Angew. Chem. , Int. Ed. 2010, 49, 4067. (d) Thirupathi, N. ; Puri, S. ; Reddy, T. J. ; Sridhar, B. ; Reddya, M. S. Adv. Synth. Catal. 2016, 358, 303. (e) Xu, P. ; Han, F. S. ; Wang, Y. H. Adv. Synth. Catal. 2015, 357, 3441. (f) Gadge, S. T. ; Khedkar, M. V. ; Lanke, S. R. ; Bhanage, B. M. Adv. Synth. Catal. 2012, 354, 2049.

    13. [13]

      (a) Kim, H. J. ; Kim, J. ; Cho, S. H. ; Chang, S. J. Am. Chem. Soc. 2011, 133, 16382. (b) Xue, Q. C. ; Xie, J. ; Li, H. M. ; Cheng, Y. X. ; Zhu, C. J. Chem. Commun. 2013, 49, 3700. (c) Zhao, D. ; Wang, T. ; Shen, Q. ; Li, J. X. Chem. Commun. 2014, 50, 4302. (d) Wei, W. ; Zhang, C. ; Xu, Y. ; Wan, X. B. Chem. Commun. 2011, 47, 10827. (e) Liu, L. H. ; Yun, L. ; Wang, Z. K. ; Fu, X. F. ; Yan, C. H. Tetrahedron Lett. 2013, 54, 5383. (f) Li, D. J. ; Yang, T. H. ; Su, H. L. ; Yu, W. Adv. Synth. Catal. 2015, 357, 2529. (g) Hao, W. J. ; Du, Y. ; Wang, D. ; Jiang, B. ; Gao, Q. ; Tu, S. J. ; Li, G. G. Org. Lett. 2016, 18, 1884. (h) Zhang, H. ; Dong, D. Q. ; Hao, S. H. ; Wang, Z. L. RSC Adv. 2016, 6, 8465. (i) Tan, B. ; Toda, N. ; Barbas, C. F. Angew. Chem. , Int. Ed. 2012, 51, 12538. (j) Sun, J. W. ; Wang, Y. ; Pan, Y. J. Org. Chem. 2015, 80, 8945. (k) Liu, Z. ; Zhang, J. ; Chen, S. ; Shi, E. ; Xu, Y. ; Wan, X. Angew. Chem. , Int. Ed. 2012, 51, 3231. (l) Uyanik, M. ; Okamoto, H. ; Yasui, T. ; Ishihara, K. Science 2010, 328, 1376.

    14. [14]

      (a) Hirao, T. ; Yamada, N. ; Ohshiro, Y. ; Agawa, T. J. Organomet. Chem. 1982, 236, 409. (b) Hosomi, A. ; Hoashi, K. ; Kohra, S. ; Tominaga, Y. ; Otaka, K. ; Sakurai, H. J. Chem. Soc. , Chem. Commun. 1987, 570.

    15. [15]

      (a) Wenkert, E. ; Han, A. -L. ; Jenny, C. -J. J. Chem. Soc. , Chem. Commun. 1988, 975. (b) Reeves, J. T. ; Fandrick, D. R. ; Tan, Z. ; Song, J. J. ; Lee, H. ; Yee, N. K. ; Senanayake, C. H. Org. Lett. 2010, 12, 4388.

    16. [16]

      Blakey, S. B.; MacMillan, D. W. C. J. Am. Chem. Soc. 2003, 125, 6046.  doi: 10.1021/ja034908b

    17. [17]

      (a) Xie, L. -G. ; Wang, Z. -X. Angew. Chem. , Int. Ed. 2011, 50, 4901. (b) Zhang, X. -Q. ; Wang, Z. -X. J. Org. Chem. 2012, 77, 3658.

    18. [18]

      Zhang, X. Q.; Wang, Z.-X. Org. Biomol. Chem. 2014, 12, 1448.  doi: 10.1039/c3ob41989d

    19. [19]

      (a) Lei, Y. ; Zhang, R. ; Wu, L. ; Wu, Q. ; Mei, H. ; Li, G. Appl. Organomet. Chem. 2014, 28, 310. (b) Lei, Y. ; Zhang, R. ; Wu, Q. ; Mei, H. ; Xiao, B. ; Li, G. J. Mol. Catal. A: Chem. 2014, 381, 120.

    20. [20]

      Rozita, Y.; Brydson, R.; Comyn, T. P.; Scott, A. J.; Hammond, C.; Brown, A.; Chauruka, S.; Hassanpour, A.; Young, N. P.; Kirkland, A. I. ChemCatChem 2013, 5, 2695.  doi: 10.1002/cctc.v5.9

    21. [21]

      Halima, T. B.; Zhang, W.; Yalaoui, I.; Hong, X.; Yang, Y.; Houk, K. N.; Newman, S. G. J. Am. Chem. Soc. 2017, 139, 1311.  doi: 10.1021/jacs.6b12329

    22. [22]

      Sun, J. W.; Fu, Y. S.; He, G. Y.; Sun, X. Q.; Wang, X. Catal. Sci. Technol. 2014, 4, 1742.  doi: 10.1039/c4cy00048j

    23. [23]

      Pillo, T.; Zimmermann, R.; Steiner, P.; Hüfner, S. J. Phys.: Condens. Matter 1997, 9, 3987.  doi: 10.1088/0953-8984/9/19/018

    24. [24]

      Murata, S.; Miura, M.; Nomura, M. J. Org. Chem. 1989, 54, 4700.  doi: 10.1021/jo00280a049

    25. [25]

      (a) North, M. Angew. Chem. , Int. Ed. 2004, 43, 4126. (b) Murahashi, S. I. ; Komiya, N. ; Terai, H. ; Nakae, T. J. Am. Chem. Soc. 2003, 125, 15312. (c) Murahashi, S. I. ; Komiya, N. ; Terai, H. Angew. Chem. , Int. Ed. 2005, 44, 6931.

    26. [26]

      Guo, S. M.; Qian, B.; Xie, Y. J.; Xia, C. G.; Huang, H. M. Org. Lett. 2011, 13, 522.  doi: 10.1021/ol1030298

    27. [27]

      Zhang, D. L.; Bao, Z.; Bao, Y. S. J. Phys. Chem. C 2015, 119, 20426.  doi: 10.1021/acs.jpcc.5b04735

    28. [28]

      Naumov, Y. A.; Dremova, V. P.; Kost, A. N.; Mentus, A. N.; Smirnova, S. N. Tr. Vses. Nauch.-Issled. Inst. Dezinfek. Steriliz. 1970, 2, 24.

    29. [29]

      Houghton, R. P.; Williams, C. S. Tetrahedron Lett. 1967, 40, 3929.

    30. [30]

      Kushner, S.; Dalalian, H.; Sanjurjo, J. L.; BachJr, F. L.; Safir, S. R.; SmithJr, V. K.; Williams, J. H. J. Am. Chem. Soc. 1952, 74, 3617.  doi: 10.1021/ja01134a045

    31. [31]

      Chow, C. T.; Chi, J. Y. Acta Chim. Sinica 1962, 28, 236 (in Chinese).

    32. [32]

      Wu, K.; Huang, Z. L.; Ma, Y. Y.; Lei, A. W. RSC Adv. 2016, 6, 24349.  doi: 10.1039/C6RA02153K

    33. [33]

      Pathak, U.; Bhattacharyya, S.; Pandey, L. K.; Mathur, S.; Jain, R. RSC Adv. 2014, 4, 3900.  doi: 10.1039/C3RA45781H

    34. [34]

      Fang, T.; Gao, X. H.; Tang, R. Y.; Zhang, X. G.; Deng, C. L. Chem. Commun. 2014, 50, 14775.  doi: 10.1039/C4CC07378A

    35. [35]

      Bao, Y. S.; Bao, A.; Bao, Z.; Bai, Y.; Jia, M. J. Org. Chem. 2014, 79, 803.  doi: 10.1021/jo4023974

    36. [36]

      Bhattacharya, A.; Plata, R. E.; Villarreal, V.; Muramulla, S.; Wu, J. Tetrahedron Lett. 2006, 47, 505.  doi: 10.1016/j.tetlet.2005.11.063

    37. [37]

      Reay, A. J.; Fairlamb, I. J. S. Chem. Commun. 2015, 51, 16289.  doi: 10.1039/C5CC06980G

  • 加载中
    1. [1]

      Zhao GuYunhui YangSong YeCongyang Wang . 2,3-Arylacylation of allenes through synergetic catalysis of palladium and N-heterocyclic carbene. Chinese Chemical Letters, 2025, 36(5): 110334-. doi: 10.1016/j.cclet.2024.110334

    2. [2]

      Xiang HuangDongzhen XuYang LiuXia HuangYangfan WuDongmei FangBing XiaWei JiaoJian LiaoMin Wang . Asymmetric synthesis of difluorinated α-quaternary amino acids (DFAAs) via Cu-catalyzed difluorobenzylation of aldimine esters. Chinese Chemical Letters, 2024, 35(12): 109665-. doi: 10.1016/j.cclet.2024.109665

    3. [3]

      Ya-Ling LiJia-Wei KeYue LiuDong-Mei YaoJing-Dong ZhangYou-Cai XiaoFen-Er Chen . Asymmetric conjugated addition of aryl Grignard reagents for the construction of chromanones bearing quaternary stereogenic centers in batch and flow. Chinese Chemical Letters, 2025, 36(6): 110377-. doi: 10.1016/j.cclet.2024.110377

    4. [4]

      Ruilong GengLingzi PengChang Guo . Dynamic kinetic stereodivergent transformations of propargylic ammonium salts via dual nickel and copper catalysis. Chinese Chemical Letters, 2024, 35(8): 109433-. doi: 10.1016/j.cclet.2023.109433

    5. [5]

      Junxin LiChao ChenYuzhen DongJian LvJun-Mei PengYuan-Ye JiangDaoshan Yang . Ligand-promoted reductive coupling between aryl iodides and cyclic sulfonium salts by nickel catalysis. Chinese Chemical Letters, 2024, 35(11): 109732-. doi: 10.1016/j.cclet.2024.109732

    6. [6]

      Hailong HeWenbing WangWenmin PangChen ZouDan Peng . Double stimulus-responsive palladium catalysts for ethylene polymerization and copolymerization. Chinese Chemical Letters, 2024, 35(7): 109534-. doi: 10.1016/j.cclet.2024.109534

    7. [7]

      Gongcheng MaQihang DingYuding ZhangYue WangJingjing XiangMingle LiQi ZhaoSaipeng HuangPing GongJong Seung Kim . Palladium-free chemoselective probe for in vivo fluorescence imaging of carbon monoxide. Chinese Chemical Letters, 2024, 35(9): 109293-. doi: 10.1016/j.cclet.2023.109293

    8. [8]

      Chengyao ZhaoJingyuan LiaoYuxiang ZhuYiying ZhangLianjie ZhaiJunrong HuangHengzhi You . Polystyrene-supported phosphoric-acid catalyzed atroposelective construction of axially chiral N-aryl benzimidazoles. Chinese Chemical Letters, 2025, 36(6): 110337-. doi: 10.1016/j.cclet.2024.110337

    9. [9]

      Jianhui YinWenjing HuangChangyong GuoChao LiuFei GaoHonggang Hu . Tryptophan-specific peptide modification through metal-free photoinduced N-H alkylation employing N-aryl glycines. Chinese Chemical Letters, 2024, 35(6): 109244-. doi: 10.1016/j.cclet.2023.109244

    10. [10]

      Guoju GuoXufeng LiJie MaYongjia ShiJian LvDaoshan Yang . Photocatalyst/metal-free sequential C–N/C–S bond formation: Synthesis of S-arylisothioureas via photoinduced EDA complex activation. Chinese Chemical Letters, 2024, 35(11): 110024-. doi: 10.1016/j.cclet.2024.110024

    11. [11]

      Shuai ZhuMingjie ChenHaichao ShenHanming DingWenbo LiJunliang Zhang . Palladium/Xu-Phos-catalyzed enantioselective arylalkoxylation reaction of γ-hydroxyalkenes at room temperature. Chinese Chemical Letters, 2024, 35(11): 109879-. doi: 10.1016/j.cclet.2024.109879

    12. [12]

      Yunqiang LiYongxian HuangSinuo LiHe HuangZhiwei Jiao . Elaborating azaaryl alkanes enabled by photoredox/palladium dual catalyzed dialkylation of azaaryl alkenes. Chinese Chemical Letters, 2025, 36(4): 110051-. doi: 10.1016/j.cclet.2024.110051

    13. [13]

      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

    14. [14]

      Jing LIANGQian WANGJunfeng BAI . Synthesis and structures of cdq-topological quaternary and (4, 4, 8)-c topological quinary Zn-MOFs with both oxalic acid and triazole ligands. Chinese Journal of Inorganic Chemistry, 2024, 40(11): 2186-2192. doi: 10.11862/CJIC.20240177

    15. [15]

      Ke ZhangSheng ZuoPengyuan YouTong RuFen-Er Chen . Palladium-catalyzed stereoselective decarboxylative [4 + 2] cyclization of 2-methylidenetrimethylene carbonates with pyrrolidone-derived enones: Straightforward access to chiral tetrahydropyran-fused spiro-pyrrolidine-2,3-diones. Chinese Chemical Letters, 2024, 35(6): 109157-. doi: 10.1016/j.cclet.2023.109157

    16. [16]

      Xiaohui FuYanping ZhangJuan LiaoZhen-Hua WangYong YouJian-Qiang ZhaoMingqiang ZhouWei-Cheng Yuan . Palladium-catalyzed enantioselective decarboxylation of vinyl cyclic carbamates: Generation of amide-based aza-1,3-dipoles and application to asymmetric 1,3-dipolar cycloaddition. Chinese Chemical Letters, 2024, 35(12): 109688-. doi: 10.1016/j.cclet.2024.109688

    17. [17]

      Liangfeng YangLiang ZengYanping ZhuQiuan WangJinheng 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

    18. [18]

      Xin LiJia-Min LuBo LiChen ZhaoBei-Bei YangLi Li . Chiroptical sensing for remote chiral amines via a C–H activation reaction. Chinese Chemical Letters, 2025, 36(5): 110310-. doi: 10.1016/j.cclet.2024.110310

    19. [19]

      Qian WuMengda XuTianjiao MaShuzhen YanJin LiXuesong Jiang . Chalcone-derived oxime esters with efficient photoinitiation properties under LED irradiation. Chinese Chemical Letters, 2025, 36(3): 110427-. doi: 10.1016/j.cclet.2024.110427

    20. [20]

      Guang XuCuiju ZhuXiang LiKexin ZhuHao Xu . Copper-catalyzed asymmetric [4+1] annulation of yne–allylic esters with pyrazolones. Chinese Chemical Letters, 2025, 36(4): 110114-. doi: 10.1016/j.cclet.2024.110114

Metrics
  • PDF Downloads(19)
  • Abstract views(1198)
  • HTML views(166)

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