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The Study Of Lewis-acid-catalyzed Reactions For The Formation Of Carbon-carbon And Carbon-heteroatom Bonds

Posted on:2009-07-08Degree:MasterType:Thesis
Country:ChinaCandidate:Z Z ShiFull Text:PDF
GTID:2121360242493623Subject:Organic Chemistry
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Transition-metal-catalyzed organic reactions for the formation of carbon–carbon and carbon–heteroatom bonds form the basis of essential and powerful strategies for the preparation of important compounds in biological, pharmaceutical, and materials sciences. Iron salts have emerged as alternative and promising catalysts for many organic transformations due to the properties of low cost, readily availability, and environmentally benign, in combination with the exceptionally high reaction rates observed and mild reaction conditions. We envisaged the application of iron catalysts in the reactions of the formation of carbon–carbon and carbon–heteroatom bonds, and we also developed other transition-metal catalyzed organic reactions in high efficiency.My job was focused on three sections as follows:1. An efficient MnCl2-catalyzed tandem acylation-cross-coupling reaction of o-halobenzoyl chloride with diorganyl magnesium compounds. We have shown a one-pot synthesis of (ortho-organyl)aryl organyl ketones, in which the organyl groups are the same, which proceeds in good yield under mild conditions.2. Iron(III) chloride catalyzed the substituted and addition reactions ofβ-dicarbonyl compounds. In this work, we have developed FeCl3 catalyzed the direct substitution of the hydroxyl group in alcohols andβ-dicarbonyl compounds, moreover addition ofβ-dicarbonyl compounds to Alkenes. This allows an easyand practical procedure for the purpose of C–C bond formation because of the inexpensive catalyst and mild condition.3. Indium(III) catalyzed addition of active methylene compounds, amine hydroxybenzene, carboxylic acid to alkenes. We have demonstrated a simple indium-salt-catalyzed addition reaction of C-H, N-H, O-H bonds to various alkenes which provides an easy and practical procedure for carbon–carbon and carbon–heteroatom bonds formation.
Keywords/Search Tags:cross-coupling reaction, tandem reaction, β-diketone compound, carbon–carbon bonds, carbon–heteroatom bonds, atom economy
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