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首页> 外文期刊>Chemistry: A European journal >Synthesis of a library of fluorescent 2-aryl-3-trifluoromethylnaphthofurans from naphthols by using a sequential pummerer-annulation/cross-coupling strategy and their photophysical properties
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Synthesis of a library of fluorescent 2-aryl-3-trifluoromethylnaphthofurans from naphthols by using a sequential pummerer-annulation/cross-coupling strategy and their photophysical properties

机译：序贯的pummerer-annulation /交叉耦合策略从萘酚合成荧光2-芳基-3-三氟甲基萘呋喃文库及其光物理性质

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摘要

A library of 2-aryl-3-trifluoromethylnaphthofurans was synthesized with high efficiency from simple naphthols. In this synthesis, the Pummerer-type annulation of naphthols with 3-(2,2,2-trifluoroethylidene)-2,4-dithiapentane 2-oxide was followed by a cross-coupling of the resulting 2-methylthio-3- trifluoromethylnaphthofurans with a variety of arylzinc reagents. A palladium complex, Pd-PEPPSI-IPr, was the most efficient catalyst for the arylation step, which represents the first cross-coupling of aryl sulfides by using an N-heterocyclic-carbene-ligated palladium complex. This library consists of new π-expanded molecules, all of which are fluorescent in the solid state as well as in solution. Their photophysical properties, such as absorption and emission, fluorescence quantum yields, and fluorescence lifetimes, were thoroughly investigated. This library was also useful to identify acidochromic molecules. Generation next: Pummerer annulation of simple naphthols followed by cross-coupling with various arylzinc reagents allows the concise and diversity-oriented synthesis of a library of fluorescent naphthofurans (see scheme).
机译：从简单的萘酚高效合成了2-芳基-3-三氟甲基萘呋喃文库。在该合成中，萘酚与3-（2,2,2-三氟亚乙基）-2,4-二硫杂戊烷2-氧化物的Pummerer型环化反应之后，是将生成的2-methylthio-3-trifluoromethylnaphthofurans与各种芳基锌试剂。钯配合物Pd-PEPPSI-IPr是芳基化步骤中最有效的催化剂，代表使用N-杂环-卡宾连接的钯配合物实现芳基硫醚的首次交叉偶联。该文库由新的π扩展分子组成，所有这些分子在固态和溶液中均发出荧光。对其吸收和发射，荧光量子产率和荧光寿命等光物理性质进行了彻底的研究。该文库还可用于鉴定酸性变色分子。下一代产品：简单的萘酚的Pummerer环环法，然后与各种芳基锌试剂交叉偶联，可实现荧光萘呋喃文库的简明且面向多样性的合成（参见方案）。

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