Regioselective syn-1,2-Hydroarylation of Internal Alkynes

IF 4.6 1区化学 Q1 CHEMISTRY, ORGANIC

Organic Chemistry Frontiers Pub Date : 2024-10-19 DOI:10.1039/d4qo01715c

Shubham Dutta, Manoj Sethi, Avijit Maity, Aradhana Sahoo, Vincent Gandon, Akhila Kumar Sahoo

引用次数: 0

Abstract

The regioselective hydro-functionalization reaction is a powerful method to convert readily available alkynes into structurally diverse olefins. Such an efficient syn-1,2-hydroarylation of yne-acetates is described herein using aryl diazonium salts and silanes as aryl and hydride sources, respectively. The transformation shows excellent functional group tolerance and applications to late-stage functionalization, providing a straightforward entry to trisubstituted allyl acetates. DFT analysis sheds light on the mechanism, particularly on the role of DMSO solvent in assisting the Si–H bond cleavage.

查看原文本刊更多论文

内部炔烃的区域选择性合成-1,2-羟基芳香化反应

区域选择性氢功能化反应是一种将容易获得的炔类化合物转化为结构多样的烯烃的有效方法。本文介绍了使用芳基重氮盐和硅烷分别作为芳基和氢化物源，对炔-乙酸酯进行这种高效的合成-1,2-氢芳基化反应。该转化过程显示出极佳的官能团耐受性，适用于后期官能化，为三取代烯丙基乙酸酯提供了直接入口。DFT 分析揭示了其机理，特别是 DMSO 溶剂在协助 Si-H 键裂解中的作用。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

求助全文

约1分钟内获得全文求助全文

来源期刊

Organic Chemistry Frontiers CHEMISTRY, ORGANIC-

CiteScore

7.90

自引率

11.10%

发文量

686

审稿时长

1 months

期刊介绍： Organic Chemistry Frontiers is an esteemed journal that publishes high-quality research across the field of organic chemistry. It places a significant emphasis on studies that contribute substantially to the field by introducing new or significantly improved protocols and methodologies. The journal covers a wide array of topics which include, but are not limited to, organic synthesis, the development of synthetic methodologies, catalysis, natural products, functional organic materials, supramolecular and macromolecular chemistry, as well as physical and computational organic chemistry.