Citation: Menggen qiqige, Wu Yun, Bao Yongsheng. Metal-Free Esterification of Aldehydes or Carboxylic Acids with Quaternary Ammonium Salts[J]. Chinese Journal of Organic Chemistry, ;2018, 38(4): 902-911. doi: 10.6023/cjoc201710034 shu

Metal-Free Esterification of Aldehydes or Carboxylic Acids with Quaternary Ammonium Salts

  • Corresponding author: Bao Yongsheng, sbbys197812@163.com
  • Received Date: 26 October 2017
    Revised Date: 26 November 2017
    Available Online: 5 April 2017

    Fund Project: Project supported by the National Natural Science Foundation of China (No. 21462031) and the Program for Young Talents of Science and Technology in Universities of Inner Mongolia Autonomous Region (No. NJYT-17-A22)the National Natural Science Foundation of China 21462031the Program for Young Talents of Science and Technology in Universities of Inner Mongolia Autonomous Region NJYT-17-A22

Figures(3)

  • A metal-free esterification of various aldehydes or carboxylic acids with quaternary ammonium salts has been developed for selective synthesis of esters. A possible mechanism containing radical process that aldehyde converts to carboxylic acid and the generation of iodohydrocarbon via C-N bond cleavage of quaternary ammonium salt is proposed.
  • 加载中
    1. [1]

      (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.

    2. [2]

      (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.

    3. [3]

      (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.
      (c) Bao, H. ; Qi, X. ; Tambar, U. K. J. Am. Chem. Soc. 2011, 133, 1206.

    4. [4]

      (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.
      (c) Guo, W. -J. ; Wang, Z. -X. Tetrahedron 2013, 69, 9580.

    5. [5]

      (a) Blakey, S. B. ; MacMillan, D. W. C. J. Am. Chem. Soc. 2003, 125, 6046.
      (b) Maity, P. ; Shacklady-McAtee, D. M. ; Yap, G. P. A. ; Sirianni, E. R. ; Watson, M. P. J. Am. Chem. Soc. 2013, 135, 280.

    6. [6]

      (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.

    7. [7]

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

    8. [8]

      (a) Uyanik, M. ; Ishihara, K. ChemCatChem 2012, 4, 177.
      (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) Sun, J. W. ; Wang, Y. ; Pan, Y. J. Org. Chem. 2015, 80, 8945.
      (j) Uyanik, M. ; Okamoto, H. ; Yasui, T. ; Ishihara, K. Science 2010, 328, 1376.
      (k) Kim, H. J. ; Kim, J. ; Cho, S. H. ; Chang, S. J. Am. Chem. Soc. 2011, 133, 16382.
      (l) Rao, H. ; Ma, X. ; Liu, Q. ; Li, Z. ; Cao, S. ; Li, C. -J. Adv. Synth. Catal. 2013, 355, 2191.

    9. [9]

      Wei, W.; Zhang, C.; Xu, Y.; Wan, X. Chem. Commun. 2011, 47, 10827.  doi: 10.1039/c1cc14602e

    10. [10]

      Liu, Z.; Zhang, J.; Chen, S.; Shi, E.; Xu, Y.; Wan, X. Angew. Chem., Int. Ed. 2012, 51, 3231.  doi: 10.1002/anie.v51.13

    11. [11]

      Zhao, J.; Li, P.; Xia, C.; Li, F. Chem. Commun. 2014, 50, 4751.  doi: 10.1039/c4cc01587h

    12. [12]

      Deshidi, R.; Rizvi, M. A.; Shah, B. A. RSC Adv. 2015, 5, 90521.  doi: 10.1039/C5RA17425B

    13. [13]

      Tan, B.; Toda, N.; Barbas, C. F. Angew. Chem., Int. Ed. 2012, 51, 12538.  doi: 10.1002/anie.201205921

    14. [14]

      Huang, J.; Li, L.; Li, H.; Husan, E.; Wang, P.; Wang, B. Chem. Commun. 2012, 48, 10204.  doi: 10.1039/c2cc35450k

    15. [15]

      (a) Fox, S. C. ; Li, B. ; Xu, D. ; Edgar, K. J. Biomacromolecules 2011, 12, 1956.
      (b) Otera, J. ; Nishikido, J. Esterification, Methods, Reactions, and Applications, 2nd ed., Wiley-VCH, Weinheim, 2010.
      (c) Otera, J. Chem. Rev. 1993, 93, 1449.
      (d) Swamy, K. C. K. ; Kumar, N. N. B. ; Balaraman, E. ; Kumar, K. V. P. P. Chem. Rev. 2009, 109, 2551.

    16. [16]

      Kouichi, M.; Hayato, S.; Yu, M.; Kazuaki, S.; Fumi, H.; Yuki, Y.; Hirotsugu, M.; Keiji, N.; Shigenori, K. J. Oleo Sci. 2014, 63, 539.  doi: 10.5650/jos.ess13199

    17. [17]

      Kong, W.; Li, B.; Xu, X.; Song, Q. J. Org. Chem. 2016, 81, 8436.  doi: 10.1021/acs.joc.6b01594

    18. [18]

      Wang, Q.; Wang, Z.; Xu, Y.; Zhang, X.; Fan, X. Asian J. Org. Chem. 2016, 5, 1304.  doi: 10.1002/ajoc.v5.11

    19. [19]

      Nulty, J.; Nair, J. J.; Sliwinski, M.; Robertson, A. J. Tetrahedron Lett. 2009, 50, 2342.  doi: 10.1016/j.tetlet.2009.02.200

    20. [20]

      Blanc, P. Y.; Perret, A.; Teppa, F. Helv. Chim. Acta 1964, 47, 567.  doi: 10.1002/hlca.19640470224

    21. [21]

      Nishii, Y.; Akiyama, S.; Kita, Y.; Mashima, K. Synlett 2015, 26, 1831.  doi: 10.1055/s-00000083

    22. [22]

      Tahmasbi, B.; Ghorbani-Choghamarani, A. Catal. Lett. 2017, 147, 649.  doi: 10.1007/s10562-016-1927-y

    23. [23]

      Cho, C. S.; Kim, D. T.; Choi, H.; Kim, T.; Shim, S. C. Bull. Korean Chem. Soc. 2002, 23, 539.  doi: 10.5012/bkcs.2002.23.4.539

    24. [24]

      Lu, B.; Zhu, F.; Sun, H.; Shen, Q. Org. Lett. 2017, 19, 1132.  doi: 10.1021/acs.orglett.7b00148

    25. [25]

      Gaspa, S.; Porcheddu, A.; De Luca, L. Org. Lett. 2015, 17, 3666.  doi: 10.1021/acs.orglett.5b01579

    26. [26]

      Subrao, M.; Potukuchi, D. M.; Ramachandra, G.; Bhagavath, P.; Bhat, S. G.; Maddasani, S. Beilstein J. Org. Chem. 2015, 11, 233.  doi: 10.3762/bjoc.11.26

    27. [27]

      Liu, H.; Eisen, M. S. Organometallics 2017, 36, 1461.  doi: 10.1021/acs.organomet.7b00101

    28. [28]

      Beller, M.; Magerlein, W.; Indolese, A. F.; Fischer, C. Synthesis 2001, 1098.

    29. [29]

      Zhu, Z.; Yuan, J.; Zhou, Y.; Qin, Y.; Xu, J.; Peng, Y. Eur. J. Org. Chem. 2014, 2014, 511.

    30. [30]

      Bhandari, K. S.; Snieckus, V. Can. J. Chem. 1971, 49, 2354.  doi: 10.1139/v71-380

  • 加载中
    1. [1]

      Mengfan ZhangLingyan LiuPeng WeiWei FengTao Yi . A proximity tagging strategy utilizing an activated aldehyde group as the active site. Chinese Chemical Letters, 2025, 36(4): 110127-. doi: 10.1016/j.cclet.2024.110127

    2. [2]

      Zhikang WuGuoyong DaiQi LiZheyu WeiShi RuJianda LiHongli JiaDejin ZangMirjana ČolovićYongge Wei . POV-based molecular catalysts for highly efficient esterification of alcohols with aldehydes as acylating agents. Chinese Chemical Letters, 2024, 35(8): 109061-. doi: 10.1016/j.cclet.2023.109061

    3. [3]

      Hong XinShutao WangLi-Na GuoCheng GuanJinyi LiaoZi-Hang YuanZhengze ZhangXin-Hua Duan . An unusual carbon radical-mediated ring-opening/amination or esterification cascade of unstrained α-haloalkyl cycloketone derivatives. Chinese Chemical Letters, 2026, 37(7): 111939-. doi: 10.1016/j.cclet.2025.111939

    4. [4]

      Xuerui SongXi HuZhengxing ZengRuikang QinTing WangHuan YangChuanfeng WangZhouyu WangXiaoqi Yu . White-light organic molecule based on structural regulation of aldehyde–gemdiol equilibrium and its applications in information encryption. Chinese Chemical Letters, 2026, 37(8): 112568-. doi: 10.1016/j.cclet.2026.112568

    5. [5]

      Xue DuZe-Hua SunPenglei ZhangLi-Ping XuXiaodong Xiong . Asymmetric chloro– and selenocyclization of 2-alkenyl anilides enabled by tertiary ammonium salt catalysis. Chinese Chemical Letters, 2026, 37(4): 111259-. doi: 10.1016/j.cclet.2025.111259

    6. [6]

      Yuexiang LiuXiangqiao YangTong LinGuantian YangXiaoyong XuBubing ZengZhong LiWeiping ZhuXuhong Qian . Efficient continuous synthesis of 2-[3-(trifluoromethyl)phenyl]malonic acid, a key intermediate of Triflumezopyrim, coupling with esterification-condensation-hydrolysis. Chinese Chemical Letters, 2025, 36(1): 109747-. doi: 10.1016/j.cclet.2024.109747

    7. [7]

      Fuyun ChiMan ZhangYiman HanFukui ShenShijie PengBo SuYuanyuan HouGang Bai . Covalent modulation of mPGES1 activity via α,β-unsaturated aldehyde group: Implications for downregulating PGE2 expression and antipyretic response. Chinese Chemical Letters, 2025, 36(4): 109913-. doi: 10.1016/j.cclet.2024.109913

    8. [8]

      Jinjie LuQikai LiuYuting ZhangYi ZhouYanbo 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

    9. [9]

      Zhi-Peng BaoHefei YangRu-Han AYuanrui WangXiao-Feng Wu . Carbonylative five-component synthesis of amides and esters with α-quaternary carbon center. Chinese Chemical Letters, 2025, 36(11): 111150-. doi: 10.1016/j.cclet.2025.111150

    10. [10]

      Saima PerveenXicheng WangTao LiLinghua WangShuai ZhangYizhao OuyangXue ZhaoLiang XuPengfei Li . Enantioconvergent reductive amidation of benzyl ammonium salts for synthesis of α-chiral amides. Chinese Chemical Letters, 2026, 37(1): 111779-. doi: 10.1016/j.cclet.2025.111779

    11. [11]

      Kang ZhangJin ZhaoPengcheng SuMingkun WangKexin WanHongwei TangDai-Huo LiuJingyu SunYihui Li . Molecular engineering strategies of ammonium vanadates for advanced zinc-ion storage. Chinese Chemical Letters, 2026, 37(7): 111831-. doi: 10.1016/j.cclet.2025.111831

    12. [12]

      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

    13. [13]

      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

    14. [14]

      Jing RenFeng-Huan DuXiaowei ChenChi Zhang . Monofluoroiodane(Ⅲ) reagent mediated Wagner−Meerwein rearrangement fluorination: Construction of quaternary C(sp3)−F bond. Chinese Chemical Letters, 2026, 37(5): 111407-. doi: 10.1016/j.cclet.2025.111407

    15. [15]

      Yuhao ZhouSiyuan WuXiaozhe RenHongjin LiShu LiTianying Yan . Effects of salt fraction on the Na+ transport in salt-in-ionic liquid electrolytes. Chinese Chemical Letters, 2025, 36(6): 110048-. doi: 10.1016/j.cclet.2024.110048

    16. [16]

      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

    17. [17]

      Quanxing MaoZhengliang WangZhinan HuZiqi YangHui LiYali YaoZijun YongTianyi Ma . Facial detection of formaldehyde by using acidichromic carbon dots and the reaction between formaldehyde and ammonium chloride. Chinese Chemical Letters, 2025, 36(7): 110499-. doi: 10.1016/j.cclet.2024.110499

    18. [18]

      Yang WANGLulu ZHANGHanjiang HEXia ZHANGXiaohong SUNFan WANGShuli WANGIn situ construction of ammonium phosphomolybdate@ZIF-8 composite for Rb+ and Cs+ adsorption performance. Chinese Journal of Inorganic Chemistry, 2026, 42(4): 826-842. doi: 10.11862/CJIC.20250332

    19. [19]

      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

    20. [20]

      Qiangwei WangHuijiao LiuMengjie WangHaojie ZhangJianda XieXuanwei HuShiming ZhouWeitai Wu . Observation of high ionic conductivity of polyelectrolyte microgels in salt-free solutions. Chinese Chemical Letters, 2024, 35(4): 108743-. doi: 10.1016/j.cclet.2023.108743

Metrics
  • PDF Downloads(12)
  • Abstract views(2877)
  • HTML views(471)

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