Photo‐catalyzed Stereospecific Synthesis of Trisubstituted Alkenes Incorporating 3,3‐Difluoro‐γ‐Lactams from Morita‐Baylis‐Hillman Acetates and N‐Allylbromodifluoroacetamides

IF 4.4 2区化学 Q2 CHEMISTRY, APPLIED

Advanced Synthesis & Catalysis Pub Date : 2024-11-01 DOI:10.1002/adsc.202401103

Jia-Yin Wang, Xi Chen, Chan Ai, Yu-Ting Wang, Hang-Dong Zuo, Jian-Wu Liu, Yue Zhang

引用次数: 0

Abstract

A photocatalytic methodology has been devised for the stereoselective construction of trisubstituted alkenes incorporating 3,3‐difluoro‐γ‐lactams in 17‐93% yields via a radical cascade process utilizing MBH acetates and N‐allylbromodifluoroacetamides as starting materials. The reaction mechanism involves single‐electron transfer, 5‐exo‐trig cyclization, radical addition, and elimination in a cascade fashion.

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由 Morita-Baylis-Hillman 醋酸盐和 N-烯丙基溴二氟乙酰胺光催化立体特异性合成掺杂 3,3-二氟-γ-内酰胺的三取代烯烃

我们设计了一种光催化方法，利用甲基溴乙酸酯和 N-烯丙基溴二氟乙酰胺作为起始材料，通过自由基级联过程，立体选择性地构建了包含 3,3-二氟-γ-内酰胺的三取代烯，收率为 17-93%。反应机理包括单电子转移、5-外-三环化、自由基加成和级联消除。

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.