Cyanosilylation of aldehydes catalyzed by ag(I)-and cu(ii)-arylhydrazone coordination polymers in conventional and in ionic liquid media

Gonçalo A. O. Tiago; Kamran T. Mahmudov; M. Fátima C. Guedes da Silva; Ana P. C. Ribeiro; Luís C. Branco; Fedor I. Zubkov; Armando J. L. Pombeiro

doi:10.3390/catal9030284

Cyanosilylation of aldehydes catalyzed by ag(I)-and cu(ii)-arylhydrazone coordination polymers in conventional and in ionic liquid media

Gonçalo A. O. Tiago, Kamran T. Mahmudov, M. Fátima C. Guedes da Silva, Ana P. C. Ribeiro, Luís C. Branco, Fedor I. Zubkov, Armando J. L. Pombeiro

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14 Citations (Scopus)

Abstract

The novel Ag(I) and Cu(II) coordination polymers [Ag(μ ₃ -1κO;2:3κO’;4κN-HL)] _n ∙n/2H ₂ O (1) and [Cu(en) ₂ (μ-1κO;2κN-L)] _n ∙nH ₂ O (2) [HL ^- = 2-(2-(1-cyano-2-oxopropylidene)hydrazinyl)benzene sulfonate] were synthesized and characterized by IR and ESI-MS spectroscopies, elemental and single crystal X-ray diffraction analyses. Compounds 1 and 2 as well as the already known complex salt [Cu(H ₂ O) ₂ (en) ₂ ](HL) ₂ (3) have been tested as homogenous catalysts for the cyanosilylation reaction of different aldehydes with trimethylsilyl cyanide, to provide cyanohydrin trimethylsilyl ethers. Coordination polymer 2 was found to be the most efficient one, with yields ranging from 76 to 88% in methanol, which increases up to 99% by addition of the ionic liquid [DHTMG][L-Lactate].

Original language	English
Article number	284
Journal	Catalysts
Volume	9
Issue number	3
DOIs	https://doi.org/10.3390/catal9030284
Publication status	Published - 1 Mar 2019

Keywords

Ag(I) and Cu(II) coordination polymers
Arylhydrazone
Catalysis
Cyanosilylation reaction
Ionic liquids

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@article{80b7d7ecf7c247eb9a1286a3a33e64d9,

title = "Cyanosilylation of aldehydes catalyzed by ag(I)-and cu(ii)-arylhydrazone coordination polymers in conventional and in ionic liquid media",

abstract = " The novel Ag(I) and Cu(II) coordination polymers [Ag(μ 3 -1κO;2:3κO{\textquoteright};4κN-HL)] n ∙n/2H 2 O (1) and [Cu(en) 2 (μ-1κO;2κN-L)] n ∙nH 2 O (2) [HL - = 2-(2-(1-cyano-2-oxopropylidene)hydrazinyl)benzene sulfonate] were synthesized and characterized by IR and ESI-MS spectroscopies, elemental and single crystal X-ray diffraction analyses. Compounds 1 and 2 as well as the already known complex salt [Cu(H 2 O) 2 (en) 2 ](HL) 2 (3) have been tested as homogenous catalysts for the cyanosilylation reaction of different aldehydes with trimethylsilyl cyanide, to provide cyanohydrin trimethylsilyl ethers. Coordination polymer 2 was found to be the most efficient one, with yields ranging from 76 to 88% in methanol, which increases up to 99% by addition of the ionic liquid [DHTMG][L-Lactate]. ",

keywords = "Ag(I) and Cu(II) coordination polymers, Arylhydrazone, Catalysis, Cyanosilylation reaction, Ionic liquids",

author = "Tiago, {Gon{\c c}alo A. O.} and Mahmudov, {Kamran T.} and Silva, {M. F{\'a}tima C. Guedes da} and Ribeiro, {Ana P. C.} and Branco, {Lu{\'i}s C.} and Zubkov, {Fedor I.} and Pombeiro, {Armando J. L.}",

note = "PD/BD/106015/2014. UID/QUI/00100/2019. KTM and APC acknowledges the FCT and Instituto Superior Tecnico (DL 57/2016 and L 57/2017 Program, Contract no: IST-ID/85/2018 and IST-ID/119/2018). ",

year = "2019",

month = mar,

day = "1",

doi = "10.3390/catal9030284",

language = "English",

volume = "9",

journal = "Catalysts",

issn = "2073-4344",

publisher = "MDPI - Multidisciplinary Digital Publishing Institute",

number = "3",

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TY - JOUR

T1 - Cyanosilylation of aldehydes catalyzed by ag(I)-and cu(ii)-arylhydrazone coordination polymers in conventional and in ionic liquid media

AU - Tiago, Gonçalo A. O.

AU - Mahmudov, Kamran T.

AU - Silva, M. Fátima C. Guedes da

AU - Ribeiro, Ana P. C.

AU - Branco, Luís C.

AU - Zubkov, Fedor I.

AU - Pombeiro, Armando J. L.

N1 - PD/BD/106015/2014. UID/QUI/00100/2019. KTM and APC acknowledges the FCT and Instituto Superior Tecnico (DL 57/2016 and L 57/2017 Program, Contract no: IST-ID/85/2018 and IST-ID/119/2018).

PY - 2019/3/1

Y1 - 2019/3/1

N2 - The novel Ag(I) and Cu(II) coordination polymers [Ag(μ 3 -1κO;2:3κO’;4κN-HL)] n ∙n/2H 2 O (1) and [Cu(en) 2 (μ-1κO;2κN-L)] n ∙nH 2 O (2) [HL - = 2-(2-(1-cyano-2-oxopropylidene)hydrazinyl)benzene sulfonate] were synthesized and characterized by IR and ESI-MS spectroscopies, elemental and single crystal X-ray diffraction analyses. Compounds 1 and 2 as well as the already known complex salt [Cu(H 2 O) 2 (en) 2 ](HL) 2 (3) have been tested as homogenous catalysts for the cyanosilylation reaction of different aldehydes with trimethylsilyl cyanide, to provide cyanohydrin trimethylsilyl ethers. Coordination polymer 2 was found to be the most efficient one, with yields ranging from 76 to 88% in methanol, which increases up to 99% by addition of the ionic liquid [DHTMG][L-Lactate].

AB - The novel Ag(I) and Cu(II) coordination polymers [Ag(μ 3 -1κO;2:3κO’;4κN-HL)] n ∙n/2H 2 O (1) and [Cu(en) 2 (μ-1κO;2κN-L)] n ∙nH 2 O (2) [HL - = 2-(2-(1-cyano-2-oxopropylidene)hydrazinyl)benzene sulfonate] were synthesized and characterized by IR and ESI-MS spectroscopies, elemental and single crystal X-ray diffraction analyses. Compounds 1 and 2 as well as the already known complex salt [Cu(H 2 O) 2 (en) 2 ](HL) 2 (3) have been tested as homogenous catalysts for the cyanosilylation reaction of different aldehydes with trimethylsilyl cyanide, to provide cyanohydrin trimethylsilyl ethers. Coordination polymer 2 was found to be the most efficient one, with yields ranging from 76 to 88% in methanol, which increases up to 99% by addition of the ionic liquid [DHTMG][L-Lactate].

KW - Ag(I) and Cu(II) coordination polymers

KW - Arylhydrazone

KW - Catalysis

KW - Cyanosilylation reaction

KW - Ionic liquids

UR - http://www.scopus.com/inward/record.url?scp=85064188798&partnerID=8YFLogxK

U2 - 10.3390/catal9030284

DO - 10.3390/catal9030284

M3 - Article

AN - SCOPUS:85064188798

SN - 2073-4344

VL - 9

JO - Catalysts

JF - Catalysts

IS - 3

M1 - 284

ER -

Cyanosilylation of aldehydes catalyzed by ag(I)-and cu(ii)-arylhydrazone coordination polymers in conventional and in ionic liquid media

Abstract

Keywords

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