DBU触发的三氟甲基酮和二氰烯烃的一锅多米诺骨牌转化为宝石-二氟烯基γ -内酰胺

IF 4 2区化学 Q2 CHEMISTRY, APPLIED

Advanced Synthesis & Catalysis Pub Date : 2025-09-26 DOI:10.1002/adsc.70090

Jian Wang , Cheng‐Feng Gao , Houwen Zhou , Feng Li , Jing Nie , Jun‐An Ma , Fa‐Guang Zhang

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引用次数: 0

摘要

三氟甲基酮直接转化为有价值的宝石二氟烯烃仍然是一种合成上有用的转化，但尚未得到充分的探索。在此，我们报道了碱催化的三氟甲基酮与二氰烯烃的一锅多米诺反应，实现了正式的双脱氧和脱氟。在温和和操作简单的条件下，该方案提供了多种宝石-二氟烯基不饱和γ -内酰胺，产率为62-95%。提出的机制包括一个顺序的葡萄醛反应，环化，重排和去氟化。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

DBU‐Triggered One‐Pot Domino Transformation of Trifluoromethyl Ketones and Dicyanoalkenes into gem‐Difluoroalkenyl γ‐Lactams

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DBU‐Triggered One‐Pot Domino Transformation of Trifluoromethyl Ketones and Dicyanoalkenes into gem‐Difluoroalkenyl γ‐Lactams

The direct conversion of trifluoromethyl ketones to valuable gem‐difluoroalkenes remains a synthetically useful but underexplored transformation. Herein, we report a base‐catalyzed, one‐pot domino reaction of trifluoromethyl ketones with dicyanoalkenes, enabling formal dual deoxygenation and defluorination. This protocol affords a diverse range of gem‐difluoroalkenyl unsaturated γ‐lactams in yields of 62–95% under mild and operationally simple conditions. A proposed mechanism involves a sequential vinylogous aldol reaction, cyclization, rearrangement, and defluorination.

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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.