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

Anand, A. S. Vijai
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Vellore Inst Technol VIT, Sch Adv Sci, Dept Chem, Vellore 632014, Tamil Nadu, India Vellore Inst Technol VIT, Sch Adv Sci, Dept Chem, Vellore 632014, Tamil Nadu, India

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[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.
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