Palladium-catalyzed C8-H alkoxycarbonylation of 1-naphthylamines with alkyl chloroformates.,Organic & Biomolecular Chemistry

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Palladium-catalyzed C8-H alkoxycarbonylation of 1-naphthylamines with alkyl chloroformates.
Organic & Biomolecular Chemistry ( IF 2.9 ) Pub Date : 2020-06-05 , DOI: 10.1039/d0ob00586j
Yaqi Shi ₁ , Fan Yang ₁ , Yangjie Wu ₁

Affiliation

A simple and efficient protocol for palladium-catalyzed C8–H alkoxycarbonylation of 1-naphthylamine derivatives with alkyl chloroformates has been developed, exhibiting broad functional group tolerance, high regioselectivity, and oxidant-free conditions. Furthermore, the reaction features its ease of further functionalization and transformation. For example, the concise synthesis of one BET bromodomain inhibitor was accomplished via benz[cd]indol-2(1H)-one after multistep transformations from the obtained alkoxycarbonylation product. In addition, the control experiments suggest that the reaction might involve a radical process and the C–H bond cleavage might not be involved in the rate-determining step.

中文翻译：

1-萘胺与烷基氯甲酸酯的钯催化C8-H烷氧基羰基化反应。

已经开发了一种简单有效的方案，用于钯催化1-萘胺衍生物与烷基氯甲酸酯的C8–H烷氧基羰基化，具有宽泛的官能团耐受性，高区域选择性和无氧化剂条件。此外，该反应具有易于进一步官能化和转化的特征。例如，从获得的烷氧羰基化产物进行多步转化后，通过苯并[ cd ]吲哚-2（1 H）-1完成了一种BET溴结构域抑制剂的简明合成。另外，对照实验表明，该反应可能涉及自由基过程，而C–H键断裂可能不参与速率确定步骤。

更新日期：2020-06-24

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