Transition-Metal-Free Radical Approach for the Synthesis of Isothiocyanates by Pyridinium 1,4-Zwitterionic Thiolates as a Sulfur Source

IF 3.6 2区 化学 Q1 CHEMISTRY, ORGANIC Journal of Organic Chemistry Pub Date : 2025-01-28 DOI:10.1021/acs.joc.4c02593
Fatemeh Abdiyan Mobarakeh, Hormoz Khosravi, Alireza Akbari, Frank Rominger, Saeed Balalaie
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Abstract

Herein, we disclose a novel, mild, transition-metal-free approach to synthesizing diversely functionalized isothiocyanates from the corresponding isocyanide precursors, achieving high to excellent yields (up to 97%). The current method sheds light on the reactivity of pyridinium 1,4-zwitterionic thiolates as an unprecedented sulfur source strikingly distinct from their previously known reactivity in ionic annulation reactions, showcasing an innovative approach to organic synthesis.

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以1,4-两性硫酸吡啶为硫源合成异硫氰酸酯的过渡-金属自由基法
在此,我们公开了一种新的,温和的,无过渡金属的方法,从相应的异氰化物前体合成不同功能化的异硫氰酸酯,实现了高到优异的收率(高达97%)。目前的方法揭示了吡啶- 1,4两性离子硫酸盐作为一种前所未有的硫源的反应性,与以前已知的离子环反应的反应性截然不同,展示了一种创新的有机合成方法。
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来源期刊
Journal of Organic Chemistry
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: 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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