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Chemistry. 2014 Jul 21;20(30):9259-62. doi: 10.1002/chem.201403497. Epub 2014 Jul 2.

Cesium carbonate catalyzed chemoselective hydrosilylation of aldehydes and ketones under solvent-free conditions.

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  • 1State Key Laboratory of Elemento-Organic Chemistry, Nankai University, Tianjin 300071 (P. R. China), Fax: (+86) 22-23503461.

Abstract

Cs2CO3 has been found to be an efficient and chemoselective catalyst for reduction of aldehydes and ketones to alcohols with one equivalent of Ph2SiH2 as the reductant under solvent-free conditions. Most of the aldehydes employed can be effectively hydrosilated quantitatively to give the corresponding silyl ethers in 2 h at room temperature, whereas the hydrosilylation of ketones proceeded smoothly at 80 °C. The catalyst system tolerates a number of functional groups including halogen, alkoxyl, olefin, ester, nitro, cyano, and heteroaromatic groups; the selective hydrosilylation of aldehydes in the presence of ketone can be effectively controlled by temperature; and hydrosilylation of α,β-unsaturated carbonyls resulted in the 1,2-addition products. The catalytic hydrosilylation of suitable dicarbonyls can be applied to the synthesis of poly(silyl ether)s with a high molecular weight and narrow molecular distribution.

© 2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

KEYWORDS:

alcohols; aldehydes; cesium carbonate; hydrosilylation; ketones; silyl ethers

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