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Issue 1, 2013
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Efficient synthesis of cyanohydrin trimethylsilyl ethers via 1,2-chemoselective cyanosilylation of carbonyls

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Abstract

Here we report a sustainable protocol for the cyanosilylation of carbonyl compounds 1a–g and 3a–m using trimethylsilyl cyanide and triphenylphosphine supported on polystyrene as a catalyst under solvent-free conditions. It has been shown that a small amount of the catalyst allows the chemoselective 1,2-addition of trimethylsilyl cyanide to α,β-unsaturated carbonyls 1a–g (5 mol%) and to saturated carbonyls 3a–m (2 mol%). The preparation of cyanohydrin trimethylsilyl ethers 2a–g and 4a–m has been accomplished in good yields (72–99%) and very low E-factor values (5–10). Finally, efficiency has been further improved by setting two different flow procedures that have allowed us to perform the representative preparation of cyanohydrin trimethylsilyl ether 4a on a large scale and with the E-factor of 0.16 or 0.47 consisting in a reduction of 90 or 72% of waste compared to our batch conditions.

Graphical abstract: Efficient synthesis of cyanohydrin trimethylsilyl ethers via 1,2-chemoselective cyanosilylation of carbonyls

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Article information


Submitted
11 Sep 2012
Accepted
02 Nov 2012
First published
02 Nov 2012

Green Chem., 2013,15, 199-204
Article type
Paper

Efficient synthesis of cyanohydrin trimethylsilyl ethers via 1,2-chemoselective cyanosilylation of carbonyls

G. Strappaveccia, D. Lanari, D. Gelman, F. Pizzo, O. Rosati, M. Curini and L. Vaccaro, Green Chem., 2013, 15, 199
DOI: 10.1039/C2GC36442E

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