Abstract
Silica gel was found to be an excellent medium for some useful organic transformations under organic solvent-free conditions, such as (1) the Friedel-Crafts-type nitration of arenes using commercial aqueous 69% nitric acid alone at room temperature, (2) one-pot Wittig-type olefination of aldehydes with activated organic halides in the presence of tributyl- or triphenylphosphine and Hunig’s base, and (3) the Morita-Baylis-Hillman reaction of aldehydes with methyl acrylate. After the reactions, the desired products were easily obtained in good to excellent yields through simple manipulation.
Highlights
IntroductionHuge amounts of organic solvents have been used and are still wasted all over the World
In the chemical industry, huge amounts of organic solvents have been used and are still wasted all over the World
We report here the successful use of silica gel as a solid reaction medium for three synthetically useful organic transformations: aromatic nitration, Wittig-type olefination, and Morita-Baylis-Hillman reaction, in which no organic solvents are required
Summary
Huge amounts of organic solvents have been used and are still wasted all over the World. There have been several approaches to access to this problem, e.g., the developments of neat reactions that proceed under various conditions such as microwave irradiation, thermal heating, grinding, sonication, etc., or in organic or inorganic solid-media, or in ionic liquid-media under organic solvent-free reactions [2,3,4,5,6,7]. In this context, we have made our own efforts to contribute to this research field developing some useful synthetic methods that do not require any organic solvents as reaction media [8,9,10,11,12]. We report here the successful use of silica gel as a solid reaction medium for three synthetically useful organic transformations: aromatic nitration, Wittig-type olefination, and Morita-Baylis-Hillman reaction, in which no organic solvents are required
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