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

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]. © 2019 by the authors. Licensee MDPI, Basel, Switzerland.

Authors
Tiago G.A.O.1 , Mahmudov K.T. 1, 2 , Guedes Da Silva M.F.C. , Ribeiro A.P.C.1 , Branco L.C.3 , Zubkov F.I. 4 , Pombeiro A.J.L. 1
Journal
Publisher
MDPI AG
Number of issue
3
Language
English
Status
Published
Number
284
Volume
9
Year
2019
Organizations
  • 1 Centro de Química Estrutural, Instituto Superior Técnico, Universidade de Lisboa, Av. Rovisco Pais, Lisboa, 1049-001, Portugal
  • 2 Department of Chemistry, Baku State University, Z. Xalilov Str. 23, Az Baku, 1148, Azerbaijan
  • 3 LAQV-REQUINTE, Departamento de Química, Faculdade de Ciências e Tecnologias da Universidade Nova de Lisboa, Quinta da Torre, Caparica, 2829-516, Portugal
  • 4 Organic Chemistry Department, Faculty of Science, Peoples’ Friendship University of Russia (RUDN University), 6 Miklukho-Maklaya St, Moscow, 117198, Russian Federation
Keywords
Ag(I) and Cu(II) coordination polymers; Arylhydrazone; Catalysis; Cyanosilylation reaction; Ionic liquids
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