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Solvent-Free and Liquid-Phase Iodination of Thiophene Derivatives with Potassium Dichloroiodate Monohydrate
Synthesis ( IF 2.2 ) Pub Date : 2020-01-23 , DOI: 10.1055/s-0039-1690795 Grigoriy Sereda 1 , Akash Mamon Sarkar 1 , Anwar Hussain 1 , Nikolai Zefirov 2
Synthesis ( IF 2.2 ) Pub Date : 2020-01-23 , DOI: 10.1055/s-0039-1690795 Grigoriy Sereda 1 , Akash Mamon Sarkar 1 , Anwar Hussain 1 , Nikolai Zefirov 2
Affiliation
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Iodination of a series of benzene and thiophene derivatives by potassium dichloroiodate monohydrate was studied with and without a solvent. The liquid substrates tend to be more reactive in water while the solid substrates afford better yields in dichloromethane or under the solvent-free conditions. The 2-substituted thiophenes show good to excellent yields whereas the yield for 3-substituted and 3,4- or 2,4-disubstituted thiophenes and benzene derivatives are significantly lower. The mechanochemical reaction of 5-carbaldehyde-2,2′-bithiophene shows excellent yields, while 2,2′-bithiophene gives practical yields only in dichloromethane. In the case of thiophene and N-acetyl-p-toluidine, electrophilic iodination is accompanied by a small extent of chlorination.
中文翻译：
二氯碘酸钾一水合物对噻吩衍生物的无溶剂液相碘化
研究了在有或没有溶剂的情况下，二氯碘酸钾一水合物对一系列苯和噻吩衍生物的碘化作用。液体底物倾向于在水中具有更高的反应性，而固体底物在二氯甲烷中或在无溶剂条件下的产率更高。2-取代的噻吩显示出良好至极好的收率，而3-取代的和3,4-或2,4-二取代的噻吩和苯衍生物的收率明显更低。5-甲醛-2,2'-联噻吩的机械化学反应显示出优异的收率，而2,2'-联噻吩仅在二氯甲烷中提供了实际收率。就噻吩和N-乙酰基-对甲苯胺而言，亲电子碘化伴随着少量氯化。
更新日期：2020-01-24
中文翻译：
二氯碘酸钾一水合物对噻吩衍生物的无溶剂液相碘化
研究了在有或没有溶剂的情况下，二氯碘酸钾一水合物对一系列苯和噻吩衍生物的碘化作用。液体底物倾向于在水中具有更高的反应性，而固体底物在二氯甲烷中或在无溶剂条件下的产率更高。2-取代的噻吩显示出良好至极好的收率，而3-取代的和3,4-或2,4-二取代的噻吩和苯衍生物的收率明显更低。5-甲醛-2,2'-联噻吩的机械化学反应显示出优异的收率，而2,2'-联噻吩仅在二氯甲烷中提供了实际收率。就噻吩和N-乙酰基-对甲苯胺而言，亲电子碘化伴随着少量氯化。
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