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Synthesis of Ferrocene Tertiary Amine Cyclopalladium Compounds and Its Application in Suzuki and Sonogashira Reactions

DOI: 10.4236/oalib.preprints.1200181, PP. 1-23

Subject Areas: Biological Chemistry, Organic Chemistry

Keywords: Ynones, Suzuki Reaction, Sonogashira Reaction, Palladium Catalyst

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Abstract

Ynones, also known as α, β-acetylenic ketones, have been widespread used in modern synthetic organic chemistry. They exist in biologically active compounds, and are used as vital building blocks in complex molecule synthesis. Consequently, a number of methodologies involving ynones have been developed to access a wide range scaffold using this simple building block. In this paper, the synthesis of a ferrocene tertiary amine cyclopalladium compounds and its application in Suzuki & Sonogashira reactions were our main works, to achieve the goal of discovering new ynones. The contents including the following three aspects: (1) The Schiff bases synthesized by ferrocene methylamine and cinnamaldehyde were underwent sodium borohydride reduction, then the corresponding cyclopalladium compounds were obtained by Mannich reaction and cyclopalladation. The structures of products were characterized by NMR spectroscopy and X-ray single crystal diffraction. (2) Suzuki coupling reactions between 3,4-dimethoxyphenylboronic acid and a series of aryl halides were studied, and several biphenyl coupling products were characterized by NMR spectroscopy. Besides, we also optimized the reaction conditions and expanded the range of substrates. (3) Sonogashira coupling reactions between phenylacetylene and series of acid chlorides were discovered, and several ynones derivatives were characterized by NMR spectroscopy. We also optimized the conditions of reaction and expanded the range of substrates.

Cite this paper

Yuan, Q. (2017). Synthesis of Ferrocene Tertiary Amine Cyclopalladium Compounds and Its Application in Suzuki and Sonogashira Reactions. Open Access Library PrePrints, 3, e181. doi: http://dx.doi.org/10.4236/oalib.preprints.1200181.

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