化学
硫酚
芳基
激进的
硫脲
光化学
离子键合
组合化学
离子
有机化学
烷基
作者
Liam T. Ball,Charlie Swan,Lorenzo Maggi,Mahri Park,Sophie Taylor,William C. Shepherd
出处
期刊:Synthesis
[Georg Thieme Verlag KG]
日期:2022-02-10
卷期号:54 (15): 3399-3408
被引量:1
标识
DOI:10.1055/s-0041-1737816
摘要
Abstract The synthetic versatility of thiophenols is offset by their air-sensitivity and foul odor. It is demonstrated that S-aryl isothiouronium salts can be used as precursors to thiyl radicals, extending the practical benefits of these air-stable, odorless salts from ionic to single electron manifolds. The isothiouronium salts are accessed via Ni-catalyzed cross-coupling of (hetero)aryl iodides and thiourea and are isolated as free-flowing solids following anion exchange. Judicious choice of a redox-innocent counteranion enables use of these convenient thiophenol surrogates in radical processes, as is exemplified by the synthesis of non-symmetrical diaryl thioethers via light-promoted S-arylation.
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