N-Oxide-Catalyzed Six-Membered Ring Bromo-etherification of ε-Alkenyl Alcohols

IF 4.4 2区化学 Q2 CHEMISTRY, APPLIED

Advanced Synthesis & Catalysis Pub Date : 2024-11-03 DOI:10.1002/adsc.202401209

Yuki Hoshino, Honoka Kasahara, Ryusei Marushima, Katsuhiko Moriyama

引用次数: 0

Abstract

A six-membered ring bromo-etherification of ε-alkenyl alcohols using N-oxide catalyst was developed to furnish 2-bromomethyl-6-substituted tetrahydropyrans with cis-selectivity and 3-bromomethyl isochromans in high yields. DFT calculations indicate that the NMO catalyst enhances the electrophilicity of the bromine atom on NBS via two hydrogen-bonding interactions after the formation of the NMO-NBS complex.

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N-氧化物催化的ε-烯醇六元环溴乙醚化反应

利用 N-oxide 催化剂开发了一种ε-烯醇的六元环溴乙醚化反应，以 cis-selectivity 合成了 2-溴甲基-6-取代的四氢吡喃，并高产率地合成了 3-溴甲基异苯并吡喃。DFT 计算表明，在 NMO-NBS 复合物形成后，NMO 催化剂通过两个氢键相互作用增强了 NBS 上溴原子的亲电性。

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

Advanced Synthesis & Catalysis 化学-应用化学

CiteScore

9.40

自引率

7.40%

发文量

447

审稿时长

1.8 months

期刊介绍： Advanced Synthesis & Catalysis (ASC) is the leading primary journal in organic, organometallic, and applied chemistry. The high impact of ASC can be attributed to the unique focus of the journal, which publishes exciting new results from academic and industrial labs on efficient, practical, and environmentally friendly organic synthesis. While homogeneous, heterogeneous, organic, and enzyme catalysis are key technologies to achieve green synthesis, significant contributions to the same goal by synthesis design, reaction techniques, flow chemistry, and continuous processing, multiphase catalysis, green solvents, catalyst immobilization, and recycling, separation science, and process development are also featured in ASC. The Aims and Scope can be found in the Notice to Authors or on the first page of the table of contents in every issue.