Premium
New Pd‐phosphorus ylide complexes based on FC 60 as heterogeneous nano‐catalyst for H/D exchange reaction
Author(s) -
Yousefi Abed,
Sabounchei Seyyed Javad,
Hashemi Ali
Publication year - 2021
Publication title -
applied organometallic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.53
H-Index - 71
eISSN - 1099-0739
pISSN - 0268-2605
DOI - 10.1002/aoc.6139
Subject(s) - chemistry , catalysis , benzoic acid , ylide , toluene , spectroscopy , nuclear chemistry , infrared spectroscopy , medicinal chemistry , organic chemistry , physics , quantum mechanics
In this account, new Pd(0) complexes of phosphorus ylides based on fullerene C 60 (FC 60 ) were synthesized and utilized as the first fullerene‐based heterogeneous nano‐catalysts for H/D exchange reaction. Four new palladacyclopropa‐[60]fullerene complexes 1 – 4 , [(η 2 ‐C 60 )Pd( Y 1–4 ) 2 ] ( Y 1 = PPh 3 CHC(O)C 6 H 4 ‐ p ‐NO 2 , Y 2 = PPh 3 CHC(O)C 6 H 4 ‐ p ‐CH 3 , Y 3 = ( p ‐tolyl) 3 P‐CHC(O)C 6 H 4 ‐ p ‐NO 2 , and Y 4 = ( p ‐tolyl) 3 P‐CHC(O)C 6 H 4 ‐ p ‐CH 3 ), were prepared through dissolving the related α‐keto stabilized phosphorus ylide in toluene solution in the presence of FC 60 and Pd (dba) 2 (dba = dibenzylideneacetone). All of the complexes were characterized using Nuclear magnetic resonance (NMR) ( 1 H, 13 C, and 31 P), Infrared spectroscopy (IR), Ultraviolet‐visible spectroscopy (UV‐visible), fluorescence, Electrospray Ionisation Mass Spectrometry (ESI‐MS), and Energy‐dispersive X‐ray spectroscopy (EDX) spectroscopies, and scanning electron microscopy (SEM) and TEM techniques. The data proved that FC 60 and two ylides were coordinated to Pd(0) center through two hexagons and two ylidic carbon atoms, respectively. An evaluation was also performed to compare the catalytic activity of synthesized Pd complex 1 and a conventional heterogeneous catalyst, 10% Pd on carbon, in H/D exchange reaction. The results indicate that the process of H/D exchange reaction in aromatic rings of benzoic acid derivatives progressed more efficiently by Pd complex 1 .