期刊
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
卷 54, 期 3, 页码 828-832出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201408721
关键词
ambiphiles; click chemistry; ionic liquids; mass spectrometry; NMR spectroscopy
资金
- CSIR
Thiol-ene click chemistry has emerged as a powerful strategy to construct carbon-heteroatom (C-S) bonds, which generally results in the formation of two regioisomers. To this end, the neutral ionic liquid [hmim]Br has been explored as a solvent cum catalyst for the synthesis of linear thioethers from activated and inactivated styrene derivatives or secondary benzyl alcohols and thiols without the requirement of using a metal complex, base, or free radical initiator. Furthermore, detailed mechanistic investigations using H-1 NMR spectroscopy and quadrupole time-of-flight electrospray ionization mass spectrometry (Q-TOF ESI-MS) revealed that the ambiphilic character of the ionic liquid promotes the nucleophilic addition of thiol to styrene through an anti-Markovnikov pathway. The catalyst recyclability and the extension of the methodology for thiol-yne click chemistry are additional benefits. A competitive study among thiophenol, styrene, and phenyl acetylene revealed that the rate of reaction is in the order of thiol-yne > thiol-ene > dimerization of thiol in [hmim]Br.
作者
我是这篇论文的作者
点击您的名字以认领此论文并将其添加到您的个人资料中。
推荐
暂无数据