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Trapping of Transient Thienyllithiums Generated by Deprotonation of 2,3- or 2,5-Dibromothiophene in a Flow Microreactor
Synlett ( IF 2 ) Pub Date : 2020-10-15 , DOI: 10.1055/s-0040-1706479
Kentaro Okano 1 , Yoshiki Yamane 1 , Aiichiro Nagaki 2 , Atsunori Mori 1, 3
Affiliation  

Selective trapping of (4,5-dibromo-2-thienyl)lithium, known to undergo halogen dance, was achieved in a flow microreactor. This transient thienyllithium, generated by mixing 2,3-dibromothiophene and lithium diisopropylamide at –78 °C for 1.6 seconds, reacted with benzaldehyde. The reaction system is also applicable to other carbonyl compounds to afford the corresponding adducts in good yields. Moreover, the established conditions permit the conversion of 2,5-dibromothiophene into a mixture of the two constitutional isomers. The contrasting results are discussed on the basis of the reaction pathway.

中文翻译:

在流动微反应器中捕获由 2,3- 或 2,5-二溴噻吩的去质子化产生的瞬态噻吩基锂

(4,5-二溴-2-噻吩基)锂的选择性捕获,已知会发生卤素舞蹈,是在流动微反应器中实现的。这种瞬态噻吩基锂是通过在 –78 °C 下将 2,3-二溴噻吩和二异丙基氨基锂混合 1.6 秒而生成的,它与苯甲醛反应。该反应体系也适用于其他羰基化合物,以良好的收率得到相应的加合物。此外,既定条件允许 2,5-二溴噻吩转化为两种结构异构体的混合物。对比结果根据反应途径进行讨论。
更新日期:2020-10-15
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