The use of arynes as the highly reactive intermediates in organic synthesis has attracted substantial attention. Particularly, the introduction of ortho-(trimethylsilyl)aryl triflates as easily activatable aryne precursors led to growing activity in this field. Most reactions using these aryne precursors proceed through the addition of nucleophiles to arynes and the subsequent trapping with electrophiles to give the multisubstituted arenes with structural diversity and complexity. Based on our studies, this review highlights the insertion of arynes, generated from ortho-(trimethylsilyl)aryl triflates, into C=O π-bond of formamides. Initially, the representative examples for formal [2+2] cycloaddition of arynes with the carbon–heteroatom double bond or the heteroatom–heteroatom double bond are shown. Next, the studies on the insertion of arynes into the N−C and C=O bonds of amide group including our three-component coupling reaction leading to oxygen heterocycles are summarized. The SN2’ reaction of tricyclic oxygen heterocycles, obtained by three-component coupling reaction, was studied by using carbon and sulfur nucleophiles. The SN2’ reaction was expanded to four-component coupling reaction. Finally, the application of tricyclic oxygen heterocycles to cysteine-selective trapping is described.

中文翻译：

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芳烃介导的氧杂环的合成及其在半胱氨酸选择性诱捕中的应用

芳烃在有机合成中作为高反应性中间体的使用已引起广泛关注。特别地，引入邻- （三甲基甲硅烷基）芳基三氟甲磺酸酯作为易于活化的芳烃前体导致该领域中活性的增长。使用这些芳烃前体的大多数反应是通过将亲核试剂添加到芳烃中并随后用亲电试剂进行捕集而得到的，具有结构多样性和复杂性的多取代芳烃。根据我们的研究，该评价亮点arynes的插入，从生成的邻- （三甲基硅烷基）三氟甲磺酸酯的芳基，成C = O π -甲酰胺键。最初，显示了具有碳-杂原子双键或杂原子-杂原子双键的芳烃的正式[2 + 2]环加成反应的代表性例子。接下来，总结了关于将芳烃插入酰胺基团的N-C和C = O键的研究，包括导致氧杂环的三组分偶联反应。通过使用碳和硫亲核试剂研究了通过三组分偶联反应获得的三环氧杂环的S N 2'反应。S N 2'反应扩展为四组分偶联反应。最后，描述了三环氧杂环在半胱氨酸选择性捕集中的应用。