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Catalysts 2019, 9(3), 284; https://doi.org/10.3390/catal9030284

Cyanosilylation of Aldehydes Catalyzed by Ag(I)- and Cu(II)-Arylhydrazone Coordination Polymers in Conventional and in Ionic Liquid Media

1
Centro de Química Estrutural, Instituto Superior Técnico, Universidade de Lisboa, Av. Rovisco Pais, 1049–001 Lisboa, Portugal
2
Department of Chemistry, Baku State University, Z. Xalilov Str. 23, Az 1148 Baku, Azerbaijan
3
LAQV-REQUINTE, Departamento de Química, Faculdade de Ciências e Tecnologias da Universidade Nova de Lisboa, Quinta da Torre, 2829-516 Caparica, Portugal
4
Organic Chemistry Department, Faculty of Science, Peoples’ Friendship University of Russia (RUDN University), 6 Miklukho-Maklaya St., Moscow 117198, Russian
*
Authors to whom correspondence should be addressed.
Received: 22 February 2019 / Revised: 13 March 2019 / Accepted: 15 March 2019 / Published: 20 March 2019
(This article belongs to the Special Issue Catalysis in Unconventional Media)
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Abstract

The novel Ag(I) and Cu(II) coordination polymers [Ag(μ3-1κO;2:3κO′;4κN-HL)]n∙n/2H2O (1) and [Cu(en)2(μ-1κO;2κN-L)]n∙nH2O (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(H2O)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]. View Full-Text
Keywords: Ag(I) and Cu(II) coordination polymers; arylhydrazone; catalysis; ionic liquids; cyanosilylation reaction Ag(I) and Cu(II) coordination polymers; arylhydrazone; catalysis; ionic liquids; cyanosilylation reaction
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited (CC BY 4.0).

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Tiago, G.A.O.; Mahmudov, K.T.; Guedes da Silva, M.F.C.; Ribeiro, A.P.C.; Branco, L.C.; Zubkov, F.I.; Pombeiro, A.J.L. Cyanosilylation of Aldehydes Catalyzed by Ag(I)- and Cu(II)-Arylhydrazone Coordination Polymers in Conventional and in Ionic Liquid Media. Catalysts 2019, 9, 284.

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