Photocatalytic Fluorosulfonylation/Fluorosulfonamidation of N-Homoallyl Aldehyde Hydrazones to Access FSO2-/FSO2N-Functionalized Tetrahydropyridazines.

IF 4.9 1区化学 Q1 CHEMISTRY, ORGANIC

Organic Letters Pub Date : 2025-07-13 DOI:10.1021/acs.orglett.5c02385

Yi-Chen Dong,Yu-Xue Ma,Yun-Fei Lu,Lin Qi,Wei Li,Li-Jing Wang

引用次数: 0

Abstract

Sulfonyl/sulfamoyl fluoride and tetrahydropyridazine cores represent pivotal structural units in chemical and medicinal science. We herein disclose a photocatalytic strategy for the fluorosulfonylation/fluorosulfonamidation of N-homoallyl aldehyde hydrazones using FABI (1-fluorosulfonyl-2-arylbenzoimidazolium triflate salts) and NFSAP (N-fluorosulfamoylpyridinium salts), enabling efficient access to sulfonyl-/sulfamoyl-substituted tetrahydropyridazines. This protocol demonstrates excellent synthetic scalability and facilitates diverse postderivatization reactions, including SuFEx click reactions and elimination processes. Preliminary mechanistic studies reveal that the transformation proceeds via a fluorosulfonyl/fluorosulfonamidyl radical-mediated cascade cyclization pathway.

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光催化氟磺化/氟磺化制备FSO2-/ fso2n功能化四氢吡啶。

磺酰/磺酰氟和四氢吡啶核心是化学和医学科学中的关键结构单元。我们在此公开了一种利用FABI（1-氟磺酰基-2-芳基苯并咪唑三酸盐）和NFSAP （n -氟磺酰基吡啶盐）进行n -纯烯丙基腙氟磺化/氟磺化的光催化策略，从而有效地获得磺酰基/磺胺酰基取代的四氢吡啶。该协议具有出色的合成可扩展性，并促进了多种衍生后反应，包括SuFEx点击反应和消除过程。初步的机制研究表明，这种转化是通过氟磺酰/氟磺酰胺自由基介导的级联环化途径进行的。

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.