Novel ruthenium-terpyridyl complex for direct oxidation of amines to nitriles

Liliana Cristian; Simona Nica; Octavian D. Pavel; Constantin Mihailciuc; Valer Almasan; Simona M. Coman; Christopher Hardacre; Vasile I. Parvulescu

doi:10.1039/c3cy00209h

Novel ruthenium-terpyridyl complex for direct oxidation of amines to nitriles

Liliana Cristian^*, Simona Nica, Octavian D. Pavel, Constantin Mihailciuc, Valer Almasan, Simona M. Coman, Christopher Hardacre, Vasile I. Parvulescu

^*Corresponding author for this work

School of Chemistry and Chemical Engineering

Research output: Contribution to journal › Article › peer-review

32 Citations (Scopus)

Abstract

High catalytic activity and selectivity has been demonstrated for the oxidation of both aliphatic and aromatic amines to nitriles under benign conditions with dioxygen or air using the Ru2Cl4(az-tpy)(2) complex. The conversion was found to be strongly influenced by the alkyl chain length of the reactant with shorter chain amines found to have lower conversions than those with longer chains. Importantly, by using the ruthenium terpyridine complex functionalized with azulenyl moiety at the 4 position of central pyridine core provided a much higher reactivity catalyst compared with a series of ruthenium terpyridine-based ligand complexes reported. Mechanistic studies using deuterated benzylamine demonstrated the importance of RuOH in this reaction.

Original language	English
Pages (from-to)	2646-2653
Number of pages	8
Journal	Catalysis Science & Technology
Volume	3
Issue number	10
Early online date	12 Jul 2013
DOIs	https://doi.org/10.1039/c3cy00209h
Publication status	Published - Oct 2013

Keywords

MOLECULAR-OXYGEN
HETEROGENEOUS OXIDATION
CATALYTIC-ACTIVITY
AEROBIC OXIDATION
DEHYDROGENATION
CONVERSION
ALCOHOLS
ALDEHYDES
SYSTEM
AMIDES

ASJC Scopus subject areas

Catalysis

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10.1039/c3cy00209h

Cite this

@article{8de08c954548450ba109db0da43419ee,

title = "Novel ruthenium-terpyridyl complex for direct oxidation of amines to nitriles",

abstract = "High catalytic activity and selectivity has been demonstrated for the oxidation of both aliphatic and aromatic amines to nitriles under benign conditions with dioxygen or air using the Ru2Cl4(az-tpy)(2) complex. The conversion was found to be strongly influenced by the alkyl chain length of the reactant with shorter chain amines found to have lower conversions than those with longer chains. Importantly, by using the ruthenium terpyridine complex functionalized with azulenyl moiety at the 4 position of central pyridine core provided a much higher reactivity catalyst compared with a series of ruthenium terpyridine-based ligand complexes reported. Mechanistic studies using deuterated benzylamine demonstrated the importance of RuOH in this reaction.",

keywords = "MOLECULAR-OXYGEN, HETEROGENEOUS OXIDATION, CATALYTIC-ACTIVITY, AEROBIC OXIDATION, DEHYDROGENATION, CONVERSION, ALCOHOLS, ALDEHYDES, SYSTEM, AMIDES",

author = "Liliana Cristian and Simona Nica and Pavel, {Octavian D.} and Constantin Mihailciuc and Valer Almasan and Coman, {Simona M.} and Christopher Hardacre and Parvulescu, {Vasile I.}",

year = "2013",

month = oct,

doi = "10.1039/c3cy00209h",

language = "English",

volume = "3",

pages = "2646--2653",

journal = "Catalysis Science & Technology",

issn = "2044-4753",

publisher = "Royal Society of Chemistry",

number = "10",

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TY - JOUR

T1 - Novel ruthenium-terpyridyl complex for direct oxidation of amines to nitriles

AU - Cristian, Liliana

AU - Nica, Simona

AU - Pavel, Octavian D.

AU - Mihailciuc, Constantin

AU - Almasan, Valer

AU - Coman, Simona M.

AU - Hardacre, Christopher

AU - Parvulescu, Vasile I.

PY - 2013/10

Y1 - 2013/10

N2 - High catalytic activity and selectivity has been demonstrated for the oxidation of both aliphatic and aromatic amines to nitriles under benign conditions with dioxygen or air using the Ru2Cl4(az-tpy)(2) complex. The conversion was found to be strongly influenced by the alkyl chain length of the reactant with shorter chain amines found to have lower conversions than those with longer chains. Importantly, by using the ruthenium terpyridine complex functionalized with azulenyl moiety at the 4 position of central pyridine core provided a much higher reactivity catalyst compared with a series of ruthenium terpyridine-based ligand complexes reported. Mechanistic studies using deuterated benzylamine demonstrated the importance of RuOH in this reaction.

AB - High catalytic activity and selectivity has been demonstrated for the oxidation of both aliphatic and aromatic amines to nitriles under benign conditions with dioxygen or air using the Ru2Cl4(az-tpy)(2) complex. The conversion was found to be strongly influenced by the alkyl chain length of the reactant with shorter chain amines found to have lower conversions than those with longer chains. Importantly, by using the ruthenium terpyridine complex functionalized with azulenyl moiety at the 4 position of central pyridine core provided a much higher reactivity catalyst compared with a series of ruthenium terpyridine-based ligand complexes reported. Mechanistic studies using deuterated benzylamine demonstrated the importance of RuOH in this reaction.

KW - MOLECULAR-OXYGEN

KW - HETEROGENEOUS OXIDATION

KW - CATALYTIC-ACTIVITY

KW - AEROBIC OXIDATION

KW - DEHYDROGENATION

KW - CONVERSION

KW - ALCOHOLS

KW - ALDEHYDES

KW - SYSTEM

KW - AMIDES

U2 - 10.1039/c3cy00209h

DO - 10.1039/c3cy00209h

M3 - Article

SN - 2044-4753

VL - 3

SP - 2646

EP - 2653

JO - Catalysis Science & Technology

JF - Catalysis Science & Technology

IS - 10

ER -

Novel ruthenium-terpyridyl complex for direct oxidation of amines to nitriles

Abstract

Keywords

ASJC Scopus subject areas

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