Argüello Juan E, Schmidt Luciana C, Peñéñory Alicia B
INFIQC, Departamento de Química Orgánica, Facultad de Ciencias Químicas, Universidad Nacional de Córdoba, Ciudad Universitaria, 5000 Córdoba, Argentina.
Org Lett. 2003 Oct 30;5(22):4133-6. doi: 10.1021/ol035545n.
[reaction: see text]. The photoinduced reactions of aryl halides with the thiourea anion afford arene thiolate ions in DMSO. These species without isolation, and by a subsequent aliphatic nucleophilic substitution, S(RN)1 reaction, oxidation, or protonation, yield aryl methyl sulfides, diaryl sulfides, diaryl disulfides, and aryl thiols with good yields (50-80%). This is a simple and convenient approach which involves the use of the commercially available and inexpensive thiourea in a "one-pot" two-step process for the synthesis of aromatic sulfur compounds.
[反应:见正文]。芳基卤化物与硫脲阴离子的光诱导反应在二甲基亚砜(DMSO)中生成芳硫醇盐离子。这些物种无需分离,通过随后的脂肪族亲核取代、S(RN)1反应、氧化或质子化,能以良好的产率(50 - 80%)生成芳基甲基硫醚、二芳基硫醚、二芳基二硫醚和芳基硫醇。这是一种简单便捷的方法,在“一锅法”两步过程中使用市售且廉价的硫脲来合成芳香族硫化合物。