Jump to main content
Jump to site search

Issue 1, 2013
Previous Article Next Article

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

Author affiliations

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

Back to tab navigation

Supplementary files

Publication details

The article was received on 11 Sep 2012, accepted on 02 Nov 2012 and first published on 02 Nov 2012


Article type: Paper
DOI: 10.1039/C2GC36442E
Citation: Green Chem., 2013,15, 199-204
  •   Request permissions

    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

Search articles by author

Spotlight

Advertisements