Photocatalytic Ring-Closing Metathesis/Amination of 1,6-Enynes and 1,7-Enynes: Synthesis of α,β-Unsaturated γ-Lactams and Quinolin-2-ones

IF 5 1区化学 Q1 CHEMISTRY, ORGANIC

Organic Letters Pub Date : 2025-05-20 DOI:10.1021/acs.orglett.5c0166810.1021/acs.orglett.5c01668

Juan Ren, Tian-Yu Sun and Xiao-Feng Xia*,

引用次数: 0

Abstract

A photocatalyzed ring-closing metathesis/amination of 1,6-enynes and 1,7-enynes using alkyl oxime esters as both an alkene deconstruction auxiliary and amination source is present for the synthesis of α,β-unsaturated γ-lactams and quinolin-2-ones. Preliminary mechanistic studies suggest that intramolecular 1,5-hydrogen atom transfer is the key to the generation of the unstabilized alkyl radicals, which subsequently promote homolytic C_α–C_β cleavage under the driving force of formation of more stable captodative radicals.

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1,6-炔和1,7-炔的光催化合环复合/胺化：α，β-不饱和γ-内酰胺和喹啉-2-酮的合成

利用烷基肟酯作为烯烃分解助剂和胺化源，光催化1,6-炔和1,7-炔的闭环复合/胺化反应，合成了α，β-不饱和γ-内酰胺和喹啉-2-酮。初步机理研究表明，分子内1,5-氢原子转移是不稳定烷基自由基生成的关键，不稳定烷基自由基在形成更稳定的俘获自由基的驱动下促进c - α - c - β均裂。

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 Letters 化学-有机化学

CiteScore

9.30

自引率

11.50%

发文量

1607

审稿时长

1.5 months

期刊介绍： Organic Letters invites original reports of fundamental research in all branches of the theory and practice of organic, physical organic, organometallic,medicinal, and bioorganic chemistry. Organic Letters provides rapid disclosure of the key elements of significant studies that are of interest to a large portion of the organic community. In selecting manuscripts for publication, the Editors place emphasis on the originality, quality and wide interest of the work. Authors should provide enough background information to place the new disclosure in context and to justify the rapid publication format. Back-to-back Letters will be considered. Full details should be reserved for an Article, which should appear in due course.