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(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].