For many years we have been developing the use of heterogeneous catalytic bases for the activation of Si-C, Si-N, Si-O bonds. In this context, we have accessed to several chemically and environmentally effective protocols that include the β-cyanation and β-azidation of alpha-beta-unsaturated ketones, ring-opening of epoxides, and also an innovative catalytic approach to a Peterson-like olefination that has allowed to replace stoichiometric amounts of wasteful and toxic supebases. Currently we are focusing our attention on the catalytic preparation and use of silyl enol ethers. These intermediates, are common reagents of choice for many reactions and they are synthetically versatile substrates for a wide range of C-C and C-X bond-forming reactions. Conventional preparations of silyl enol ethers employed a silyl chlorides/base combination and need careful attention during work-up of the reaction and isolation of the enol ethers. In this communication, we report our recent results on the definition of a protocol for the preparation of silyl enol ethers starting from aryl or alkyl ketones based on the combination of solvent-free conditions (SolFC), BSA (bis trimethylsilyl acetamide) as silylating agent used in equimolar amount and a polymer-supported base as catalyst. Such procedure is also suitable for in situ reaction with a variety of reagents to yield a wide array of fine chemicals.

Green protocol for the preparation of silyl enol ethers and their application in the synthesis of fine chemicals

253rd National Meeting (2017)

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