Constructing less-conjugated olefins via unusual regioselective hydrogen atom transfer from acetals

IF 4.6 1区化学 Q1 CHEMISTRY, ORGANIC Organic Chemistry Frontiers Pub Date : 2025-01-14 DOI:10.1039/d4qo02099e

Zhaoshan Wang, Huiying Liu, Tian-Tian Liu, Qixiang Wang, Youhao Wei, Xiaoguang Bao, Xinxin Wu

引用次数: 0

Abstract

Utilizing a regioselective hydrogen atom transfer (RHAT) strategy, this study demonstrates a triple RHAT process accompanied by C–O bond homolysis to generate unusual less-conjugated or contra-thermodynamic olefins, a transformation rarely documented in the literature. The key to this conversion is the uncommon RHAT from the secondary ether C–H bond, rather than the weaker tertiary acetal C–H bond. This protocol offers a diverse class of synthetically versatile, less-conjugated, or contra-thermodynamic olefins.

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本研究利用区域选择性氢原子转移（RHAT）策略，展示了伴随着 C-O 键均解的三重 RHAT 过程，生成了不寻常的低共轭或反热力学烯烃，这种转化在文献中很少见。这种转化的关键在于从二级醚 C-H 键而不是较弱的三级缩醛 C-H 键进行不常见的 RHAT。该方案可合成多种用途广泛、共轭度较低或反热力学的烯烃。

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

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.