Stereo- and Regioselective Installation of Vinyl Sulfonyl Fluoride onto Indoles without Transition-Metal Catalyst.

IF 3.3 2区 化学 Q1 CHEMISTRY, ORGANIC The Journal of Organic Chemistry Pub Date : 2024-09-24 DOI:10.1021/acs.joc.4c01689
Shu-Zhen Zheng, Eman Fayad, Najla A Alshaye, Hua-Li Qin
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Abstract

Herein, we developed a practical method for synthesizing a class of novel and highly valuable indolyl vinyl sulfonyl fluorides. This protocol has carved out a path for constructing a broad range of vinyl sulfonyl fluorinated indoles with exclusive stereo- and regioselectivity through the Friedel-Crafts/elimination reaction without any transition-metal catalyst. This transformation features mild conditions, high efficiency, excellent selectivity, and rich substrate compatibility, highlighting its significant value in medicinal chemistry and many related disciplines.

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在无过渡金属催化剂的情况下,将乙烯基磺酰氟立体和区域选择性地安装到吲哚上。
在此,我们开发了一种合成一类新型高价值吲哚基乙烯磺酰氟的实用方法。该方法通过弗里德尔-卡夫斯/消除反应,在不使用任何过渡金属催化剂的情况下,构建了一系列具有独特立体和区域选择性的乙烯基磺酰氟吲哚。这一转化过程具有条件温和、效率高、选择性好和底物兼容性强等特点,在药物化学和许多相关学科中具有重要价值。
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来源期刊
The Journal of Organic Chemistry
The Journal of Organic Chemistry 化学-有机化学
CiteScore
6.20
自引率
11.10%
发文量
1467
审稿时长
2 months
期刊介绍: The Journal of Organic Chemistry welcomes original contributions of fundamental research in all branches of the theory and practice of organic chemistry. In selecting manuscripts for publication, the editors place emphasis on the quality and novelty of the work, as well as the breadth of interest to the organic chemistry community.
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