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Studies on Copper-catalyzed Reactions Between Arylboronic Acids and Alddhydes

Author: ZhengHanMei
Tutor: DingJinChang；WuHuaYue
School: Wenzhou University
Course: Organic Chemistry
Keywords: aldehyde arylboronic acid copper-catalyzed addition reaction coupling reaction
CLC: O621.25
Type: Master's thesis
Year: 2010
Downloads: 68
Quote: 0
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Abstract


Arylboronic acids enjoy high prestige in the metal-catalyzed C-C bond formation due to their advantages of relative stability toward moisture and air, good functional group tolerance and ease of synthesis. In recent years, great attention has been paid to the transition metal-catalyzed addition of arylboronic acids to unsaturated carbon-oxygen bond. In this paper, recent advances in the metal-catalyzed reactions between arylboronic acids and aldehydes were reviewed, then two kinds of reactions were studied: (1) In the presence of copper(II) acetate and dppf ligand, diarylmethanol compounds were generated from the addition of arylboronic acids to aromatic aldehydes in good to excellent yields. The important features of this methodology are no requirement of rigorous exclusion of air/moisture; (2) copper(II) trifluomethanesulfonate-catalyzed synthesis of diaryl ketone compounds from aldehydes by coupling reaction with arylboronic acids. In the course of the study found product may involve two steps,in which diaryl ketones are compared by the corresponding diarylmethanols produced in situ by addition reaction between arylboronic acids and aldehydes.The new approach for the synthesis of diarylmethanol compounds, diaryl ketone compounds are developed, which enjoy the advantages of mild reaction conditions, commercially available materials, simple operation and moderate to high yields.

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CLC: > Mathematical sciences and chemical > Chemistry > Organic Chemistry > Organic Chemistry general issues > Properties of organic compounds > Chemical properties of organic reactions
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