Tunable Preparation of α‐Aminoacyl Fluorides and α‐Fluoroamides via Base‐Induced Cascade Multiple‐Cleavage Processes from Bromodifluorohydrin Reagents and Amines

IF 4 2区化学 Q2 CHEMISTRY, APPLIED

Advanced Synthesis & Catalysis Pub Date : 2025-09-26 DOI:10.1002/adsc.70083

Giulia De Santis , Andrea Maranzana , Federica Lauria , Mauro Spennacchio , Michael Andresini , Rosa Purgatorio , Marco Colella , Renzo Luisi , Leonardo Degennaro

引用次数: 0

Abstract

A concise strategy for the divergent synthesis of α‐fluoroamides and α‐aminoacyl fluorides is developed via multiple bond‐cleavage processes of 2‐bromo‐2,2‐difluoro alcohols in the presence of amines. The transformation proceeds under mild conditions, displays a broad substrate scope, and features operational simplicity. Mechanistic studies, supported by density functional theory calculations, suggest the involvement of a putative gem‐difluoroepoxide intermediate that triggers a cascade of atom recombination events.

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溴代氟丙烷试剂和胺的碱诱导级联多重裂解制备α-氨基酰氟化物和α-氟酰胺的研究

通过2-溴-2,2-二氟醇在胺存在下的多重键裂解过程，建立了α-氟酰胺和α-氨基酰氟化合物的合成策略。该转化在温和的条件下进行，显示出广泛的衬底范围，并且具有操作简单的特点。由密度泛函理论计算支持的机制研究表明，假定的宝石-二氟环氧化物中间体参与了触发一连串原子重组事件的过程。

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.