Facile InCl 3-catalyzed room temperature synthesis and electrochemical behavior of ferrocene appended (R, S)- α-aminophosphonates

被引:1
|
作者
Anand, A. S. Vijai [1 ]
Sivaramakrishna, Akella [1 ]
机构
[1] Vellore Inst Technol VIT, Sch Adv Sci, Dept Chem, Vellore 632014, Tamil Nadu, India
关键词
Ferrocene-appended alpha-aminophosphonates; Kabachnik-Fields reaction; Structural aspects; InCl3-catalysis; Electrochemical studies; CATALYST;
D O I
10.1016/j.molstruc.2024.138361
中图分类号
O64 [物理化学(理论化学)、化学物理学];
学科分类号
070304 ; 081704 ;
摘要
alpha-Aminophosphonates represent a significant category of the phosphorus family. Due to the additional 'N ' atom (s), these compounds exhibit interesting electronic, coordination, and electrochemical properties. In this regard, the present work is focused on the In(III)-catalyzed synthesis of new ferrocene-appended alpha-aminophosphonates using the well-known Kabachnik-Fields reaction. Notably, all the reactions proceed to complete at room temperature in ethanol to provide the products with excellent yields in the range of 87 - 95%. The reaction proceeded smoothly with a broader substrate scope containing -Cl, Br, F, NO 2 , t -butyl, and 3,5-dimethyl substituents at various positions. The purity of the products was assessed by analytical and spectroscopic techniques including 1 H, 13 C and 31 P NMR along with HR -MS spectroscopic analysis. Among 18 compounds, 17 derivatives were crystallized in triclinic and monoclinic systems with P-1, P2 1 /n, or P2 1 /c space groups. From the results, the length of P = O bonds exhibits a range spanning from 1.447(2) & Aring; ( 4c ) to 1.469(2) & Aring; ( 4l ). Additionally, the electrochemical studies of all the synthesized compounds showed an effective redox response. The presence of the phosphoryl group and the substituents have a distinct influence on the electrochemical behavior of the synthesized molecules.
引用
下载
收藏
页数:11
相关论文
共 17 条
  • [1] A facile Er(OTf)3-catalyzed synthesis of 2,3-unsaturated O- and S-glycosides
    Procopio, Antonio
    Dalpozzo, Renato
    De Nino, Antonio
    Maluolo, Loredana
    Nardi, Monica
    Oliverio, Manuela
    Russo, Beatrice
    CARBOHYDRATE RESEARCH, 2007, 342 (14) : 2125 - 2131
  • [2] Facile synthesis of bis(indolyl)methanes catalyzed by ferric dodecyl sulfonate [Fe(DS)3] in water at room temperature
    Wang, Shun-Yi
    Ji, Shun-Jun
    SYNTHETIC COMMUNICATIONS, 2008, 38 (08) : 1291 - 1298
  • [3] Facile synthesis and electrochemical application of surface-modified Bi2S3 urchin-like nano-spheres at room temperature
    Zhou, Xiaodong
    Shi, Huaqiang
    Zhang, Bo
    Fu, Xun
    Hao, Kui
    MATERIALS LETTERS, 2008, 62 (17-18) : 3201 - 3204
  • [4] The facile synthesis of PbS cubes and Bi2S3 nanoflowers from molecular precursors at room temperature
    Sun, Shan-shan
    Han, Qiao-feng
    Wu, Xiao-dong
    Zhu, Jun-wu
    Wang, Xin
    MATERIALS LETTERS, 2011, 65 (21-22) : 3344 - 3347
  • [5] PPh3-catalyzed Mannich reaction: a facile one-pot synthesis of β-amino carbonyl compounds under solvent-free conditions at room temperature
    Javad Abedini-Torghabeh
    Hossein Eshghi
    Mehdi Bakavoli
    Mohammad Rahimizadeh
    Research on Chemical Intermediates, 2015, 41 : 3649 - 3658
  • [6] Palladium-catalyzed alkylation of unactivated C(sp3)-H bonds with primary alkyl iodides at room temperature: facile synthesis of β-alkyl α-amino acids
    Wang, B.
    Wu, X.
    Jiao, R.
    Zhang, S. -Y.
    Nack, W. A.
    He, G.
    Chen, G.
    ORGANIC CHEMISTRY FRONTIERS, 2015, 2 (10): : 1318 - 1321
  • [7] PPh3-catalyzed Mannich reaction: a facile one-pot synthesis of β-amino carbonyl compounds under solvent-free conditions at room temperature
    Abedini-Torghabeh, Javad
    Eshghi, Hossein
    Bakavoli, Mehdi
    Rahimizadeh, Mohammad
    RESEARCH ON CHEMICAL INTERMEDIATES, 2015, 41 (06) : 3649 - 3658
  • [8] Room Temperature Synthesis of Cu2Sn(S,Se)3 Thin Film by Facile Arrested Precipitation Technique for Photoelectrochemical Cell Application
    Joshi, Monika P.
    Bhosale, P. N.
    4TH INTERNATIONAL CONFERENCE ON EMERGING TECHNOLOGIES; MICRO TO NANO, 2019: (ETMN 2019), 2021, 2335
  • [9] Naturally Occurring Organic Acid-catalyzed Facile Diastereoselective Synthesis of Biologically Active (E)-3-(arylimino)indolin-2-one Derivatives in Water at Room Temperature
    Kaur, Gurpreet
    Singh, Arvind
    Bala, Kiran
    Devi, Mamta
    Kumari, Anjana
    Devi, Sapna
    Devi, Rekha
    Gupta, Vivek Kumar
    Banerjee, Bubun
    CURRENT ORGANIC CHEMISTRY, 2019, 23 (16) : 1778 - 1788
  • [10] Visible photoassisted room-temperature oxidizing gas-sensing behavior of Sn2S3 semiconductor sheets through facile thermal annealing
    Yuan-Chang Liang
    Tsai-Wen Lung
    Chein-Chung Wang
    Nanoscale Research Letters, 2016, 11