Quinones represent a ubiquitous class of natural products, extensively distributed throughout nature. Within these organisms, they fulfil pivotal roles across a spectrum of metabolic processes essential to the organisms. Their privileged core structure is present in a variety of substances explored in medicinal chemistry. Modification of the central core of quinones could give rise to new substances with great potential as drug candidates. In this context, the introduction of an aryl or heteroaryl moiety on the quinone structure can be an important strategy for the development of new potentially bioactive compounds. In the present work, direct arylation methods of quinones reported in the literature are summarized, restricting the text to methods where organometallics are not used as catalysts, nor are organometallic species formed during the catalytic cycle. Radical arylation methods are presented where diazonium salts, hydrazines and arylboronic acids are used as aryl radicals’ sources, thermally and photochemically generated. Polar reactions are also presented, that is, through nucleophiles and electrophiles. In most reports, rich aromatics acts as nucleophiles against naphthoquinones, whose electrophilicity is increased by an Brönsted or Lewis acid. Quinones can be the starting materials or generated in situ from phenolic precursors.

中文翻译：

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苯醌和萘醌直接芳基化的无有机金属方法


醌代表一类普遍存在的天然产物，广泛分布于自然界中。在这些生物体中，它们在生物体必需的一系列代谢过程中发挥着关键作用。它们独特的核心结构存在于药物化学探索的多种物质中。醌核心的修饰可能会产生作为候选药物具有巨大潜力的新物质。在这种情况下，在醌结构上引入芳基或杂芳基部分可能是开发新的潜在生物活性化合物的重要策略。在本工作中，总结了文献中报道的醌的直接芳基化方法，将文本限制为不使用有机金属作为催化剂，也不在催化循环过程中形成有机金属物质的方法。提出了自由基芳基化方法，其中重氮盐、肼和芳基硼酸用作芳基自由基的来源，通过热和光化学产生。还存在极性反应，即通过亲核试剂和亲电试剂。在大多数报告中，丰富的芳族化合物充当萘醌的亲核试剂，其亲电性通过布朗斯特酸或路易斯酸而增加。醌可以是起始材料或由酚类前体原位产生。