通过乙烯磺酰氟和邻羟基芳基偶氮甲烷的串联 [3+2] 环加成-SuFEx 点击反应，在布氏碱催化下组装磺基苯并[4,3-b]吡咯烷类化合物

IF 4.7 1区化学 Q1 CHEMISTRY, ORGANIC

Organic Chemistry Frontiers Pub Date : 2024-09-05 DOI:10.1039/D4QO01325E

Fang Zhang, Qichao Zhang, Pei Xie, Lin He, Zhihua Cai and Guangfen Du

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引用次数: 0

摘要

本文介绍了磺基色烯并[4,3-b]吡咯烷的合成。在 20 mol% Brønsted 碱催化下，以分子筛 4Å 作为 HF 清除剂，邻羟基芳基偶氮甲烷与乙烯磺酰氟通过串联 [3+2] 环化-SuFEx 点击反应，高产率地生成磺基色并[4,3-b]吡咯烷。根据 19F NMR 实验和 DFT 计算，提出了合理的反应机理。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

Brønsted base-catalyzed assembly of sulfochromeno[4,3-b]pyrrolidines via tandem [3 + 2] cycloaddition–SuFEx click reaction of ethenesulfonyl fluorides and o-hydroxyaryl azomethines†

查看原文本刊更多论文

Brønsted base-catalyzed assembly of sulfochromeno[4,3-b]pyrrolidines via tandem [3 + 2] cycloaddition–SuFEx click reaction of ethenesulfonyl fluorides and o-hydroxyaryl azomethines†

The synthesis of sulfochromeno[4,3-b]pyrrolidines is described. Under the catalysis of a 20 mol% Brønsted base and using molecular sieves 4 Å as an HF scavenger, o-hydroxyaryl azomethines react with ethenesulfonyl fluorides through a tandem [3 + 2] cyclization–SuFEx click reaction to produce sulfochromeno[4,3-b]pyrrolidines in high yields. A reasonable reaction mechanism was proposed based on ¹⁹F NMR experiments and DFT calculations.

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来源期刊

Organic Chemistry Frontiers CHEMISTRY, ORGANIC-

CiteScore

7.90

自引率

11.10%

发文量

686

审稿时长

1 months

期刊介绍： Organic Chemistry Frontiers is an esteemed journal that publishes high-quality research across the field of organic chemistry. It places a significant emphasis on studies that contribute substantially to the field by introducing new or significantly improved protocols and methodologies. The journal covers a wide array of topics which include, but are not limited to, organic synthesis, the development of synthetic methodologies, catalysis, natural products, functional organic materials, supramolecular and macromolecular chemistry, as well as physical and computational organic chemistry.