Acid-catalyzed regioselective remote heteroarylation of alkenes via CC bond migration†

IF 11.3 1区化学 Q1 CHEMISTRY, PHYSICAL

ACS Catalysis Pub Date : 2024-09-30 DOI:10.1039/d4gc03356f

Shengxiang Qin , Yaqi Zhang , Long Jiang , Man Kin Tse , Albert S. C. Chan , Liqin Qiu

引用次数: 0

Abstract

We report herein the acid-catalyzed regioselective remote heteroarylation and reductive alkylation of alkenes. Various alkenes, including mono-, di-, and tri-substituted alkenes and cyclic alkenes, are applicable to this reaction. This method exhibits broad substrate scope, high functional group tolerance and high atomic economy. In addition, both gram-scale synthesis and product transformations demonstrate the potential utility of this reaction. It also provides an efficient and novel pathway to establish the valuable framework of 1,1-diaryl alkanes. Further mechanistic studies suggested that TfOH in situ generated by Cu(OTf)₂ and trace H₂O catalyzed the alkene migration. Then, heteroarylation was conducted by Friedel–Crafts type alkylation.

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通过 CC 键迁移实现酸催化烯烃的区域选择性远程杂芳基化

我们在此报告了酸催化的烯烃区域选择性远程杂芳基化和还原烷基化反应。包括一、二、三取代烯烃和环烯烃在内的各种烯烃都适用于该反应。这种方法具有底物范围广、官能团耐受性高和原子经济性高等特点。此外，克级规模的合成和产物转化都证明了这一反应的潜在用途。它还为建立有价值的 1,1-二芳基烷烃框架提供了一条高效而新颖的途径。进一步的机理研究表明，由 Cu(OTf)2 和痕量 H2O 原位生成的 TfOH 催化了烯的迁移。然后，通过 Friedel-Crafts 型烷基化反应进行杂芳基化。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

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来源期刊

ACS Catalysis CHEMISTRY, PHYSICAL-

CiteScore

20.80

自引率

6.20%

发文量

1253

审稿时长

1.5 months

期刊介绍： ACS Catalysis is an esteemed journal that publishes original research in the fields of heterogeneous catalysis, molecular catalysis, and biocatalysis. It offers broad coverage across diverse areas such as life sciences, organometallics and synthesis, photochemistry and electrochemistry, drug discovery and synthesis, materials science, environmental protection, polymer discovery and synthesis, and energy and fuels. The scope of the journal is to showcase innovative work in various aspects of catalysis. This includes new reactions and novel synthetic approaches utilizing known catalysts, the discovery or modification of new catalysts, elucidation of catalytic mechanisms through cutting-edge investigations, practical enhancements of existing processes, as well as conceptual advances in the field. Contributions to ACS Catalysis can encompass both experimental and theoretical research focused on catalytic molecules, macromolecules, and materials that exhibit catalytic turnover.