Cyanosilylation of aldehydes catalyzed by arylhydrazone di-and triorganotin(IV) complexes

Two known organotin(IV) complexes, [Sn(C6H5)(3)HL1] (1) and [Sn(C2H5)(2)(1 kappa O, 2 kappa O-H3L2) (1 kappa O-2-H3L2) (mu(3)-O)](2) (2), were prepared upon interaction of Ph3SnCl and Et2SnO with 2-(2-(2,4-dioxopentan-3-ylidene) hydrazinyl) benzoic acid (H2L1) and 2-(2-(2,4,6-trioxotetrahydropyrimidin-5(2H)-ylidene) hydrazinyl) benzoic acid (H4L2), respectively, in toluene solution. Both complexes are applied as catalysts in cyanosilylation of aldehydes. Complex 2 shows a high catalytic activity in the cyanosilylation reaction of a variety of aliphatic and aromatic aldehydes with trimethylsilyl cyanide yielding to the corresponding cyanohydrin trimethylsilyl ethers (yields up to 99%) in methanol and at room temperature. (C) 2017 Elsevier B.V. All rights reserved.