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Exploration of amination reactions on highly extendable active sites of Pd(II)-3-allylsalicylaldiminophenol (ASIP) complex over thiofunctionalized SBA-15

Exploration of amination reactions on highly extendable active sites of Pd(II)-3-allylsalicylaldiminophenol (ASIP) complex over thiofunctionalized SBA-15
Exploration of amination reactions on highly extendable active sites of Pd(II)-3-allylsalicylaldiminophenol (ASIP) complex over thiofunctionalized SBA-15
An effective and impressive heterogeneous catalyst, Pd(II)-3-allylsalicylaldiminophenol-SBA-15, dubbed as Pd(II)ASIP@SBA-15, for amination reactions of aryl halides to synthesize secondary amines (20), has been synthesized and characterized. Pd(II)ASIP@SBA-15 has been synthesized by the covalent anchoring of 3-allylsalicylaldehyde over thiofunctionalized SBA-15, then further reaction with 2-aminophenol, followed by metallation process by using Pd(II)(OAc)2. A specifically designed cheap and easily available organic ligand, 3-allylsalicylaldiminophenol (ASIP), was synthesized from 3-allylsalicylaldehyde and 2-aminophenol. Using this, the synthesis of Pd(II)ASIP@SBA-15 was carried out whereby the ligand providing an active co-ordination or chelating sites for palladium metal. This strategy helped in exposing the Pd(II)ASIP active sites from surface to channels of SBA-15 support during the reactions. The synthesized catalyst were characterized by CHN analysis, PXRD, Nitrogen sorption analyses, TG & DTA, FTIR, 13C and 29Si CPMASS NMR spectra, XPS, UV–Visible, SEM, EDAX and TEM. Pd(II)ASIP@SBA-15 catalyst was screened in heterogeneous amination reactions of aryl halides to produce N-aryl derivatives or secondary amines with high catalytic activity as revealed by turn over frequency (TOF) calculations. To explore the heterogeneous nature of catalysts, amination reactions were carried with neat Pd(II)ASIP complex and Pd(II)(OAc)2 catalysts. The catalyst was recycled several times without much loss of activity and Sheldon hot filtration test has been performed.
173-181
Lazar, Anish
f01c546a-a2e1-4b7b-a121-dd6e06de6b61
Vinod, Chathakudath P.
02386bb6-9b4a-4904-99e2-8c7702ebf582
Singh, A.P.
df443df3-4520-4abc-9aff-09160821b030
Lazar, Anish
f01c546a-a2e1-4b7b-a121-dd6e06de6b61
Vinod, Chathakudath P.
02386bb6-9b4a-4904-99e2-8c7702ebf582
Singh, A.P.
df443df3-4520-4abc-9aff-09160821b030

Lazar, Anish, Vinod, Chathakudath P. and Singh, A.P. (2017) Exploration of amination reactions on highly extendable active sites of Pd(II)-3-allylsalicylaldiminophenol (ASIP) complex over thiofunctionalized SBA-15. Microporous and Mesoporous Materials, 242, 173-181. (doi:10.1016/j.micromeso.2017.01.026).

Record type: Article

Abstract

An effective and impressive heterogeneous catalyst, Pd(II)-3-allylsalicylaldiminophenol-SBA-15, dubbed as Pd(II)ASIP@SBA-15, for amination reactions of aryl halides to synthesize secondary amines (20), has been synthesized and characterized. Pd(II)ASIP@SBA-15 has been synthesized by the covalent anchoring of 3-allylsalicylaldehyde over thiofunctionalized SBA-15, then further reaction with 2-aminophenol, followed by metallation process by using Pd(II)(OAc)2. A specifically designed cheap and easily available organic ligand, 3-allylsalicylaldiminophenol (ASIP), was synthesized from 3-allylsalicylaldehyde and 2-aminophenol. Using this, the synthesis of Pd(II)ASIP@SBA-15 was carried out whereby the ligand providing an active co-ordination or chelating sites for palladium metal. This strategy helped in exposing the Pd(II)ASIP active sites from surface to channels of SBA-15 support during the reactions. The synthesized catalyst were characterized by CHN analysis, PXRD, Nitrogen sorption analyses, TG & DTA, FTIR, 13C and 29Si CPMASS NMR spectra, XPS, UV–Visible, SEM, EDAX and TEM. Pd(II)ASIP@SBA-15 catalyst was screened in heterogeneous amination reactions of aryl halides to produce N-aryl derivatives or secondary amines with high catalytic activity as revealed by turn over frequency (TOF) calculations. To explore the heterogeneous nature of catalysts, amination reactions were carried with neat Pd(II)ASIP complex and Pd(II)(OAc)2 catalysts. The catalyst was recycled several times without much loss of activity and Sheldon hot filtration test has been performed.

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Accepted/In Press date: 15 January 2017
e-pub ahead of print date: 19 January 2017
Published date: April 2017

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Local EPrints ID: 435017
URI: http://eprints.soton.ac.uk/id/eprint/435017
PURE UUID: fa73a469-f1b4-4dac-a7d9-cf1b6a4f3b15

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Date deposited: 18 Oct 2019 16:30
Last modified: 06 Oct 2020 21:02

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