Copper‐catalyzed intramolecular N—H/C—H annulation with alkynes has been developed. A variety of densely functionalized heterocycles, such as pyrrolo[1,2‐a]indoles, indolo[1,2‐c]quinazolin‐2‐ones, oxazolo[3,4‐a]indoles, and imidazo[1,5‐a]indoles, were synthesized in an atom‐ and step‐economical manner, owing to the high modularized feature of aniline moiety, the linker moiety, as well as the alkyne moiety. By simply changing the oxidant from di‐tert‐butyl peroxide (DTBP) to 2,2,6,6‐tetramethylpiperidine‐1‐oxyl (TEMPO), the reaction could readily be transformed to the aminooxygenation pathway, which grabs one oxygen atom from the TEMPO to generate 5‐aroyl‐pyrrol‐2‐ones. Mechanistic experiments indicate that vinyl radical is involved in this reaction and an amidyl‐radical‐initiated radical cascade might be responsible for this transformation.

中文翻译：

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铜催化通过炔烃的分子内NH / CH-H环化法获得N稠合的多环吲哚和5-芳基吡咯-2-酮的范围和作用机理

已经开发了使用炔烃的铜催化分子内NH / CH环合反应。各种稠密官能化的杂环，如吡咯并[1,2- a ]吲哚，吲哚并[1,2 - c ]喹唑啉-2-酮，恶唑并[3,4- a ]吲哚和咪唑[1,5-由于苯胺部分，连接子部分和炔烃部分具有高度模块化的特征，因此以原子和分步经济的方式合成了α ]吲哚。通过简单地改变从二氧化剂叔将过氧化叔丁基（DTBP）转化为2,2,6,6-四甲基哌啶-1-氧基（TEMPO），该反应很容易转化为氨氧化途径，该途径从TEMPO夺取一个氧原子以生成5-芳酰基吡咯2个 机理实验表明，乙烯基自由基参与了该反应，而酰胺基自由基引发的自由基级联反应可能是造成这种转变的原因。