Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 24, Issue 63, Pages 16895-16901Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201804229
Keywords
amination; isoindolinones; oxidation; photoredox catalysis; redox catalysis
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Funding
- NNSFC [21472057, 21472058, 21622201, 21772053]
- Science and Technology Department of Hubei Province [2016CFA050, 2017AHB047]
- Program of Introducing Talents of Discipline to Universities of China (111 Program) [B17019]
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A new synergistic multicatalytic activation mode of eosin Y has been discovered by exploiting the redox potential of its ground state and excited state. This catalytic strategy proves to be an enabling tool for visible-light-driven sequential benzylic C-H amination and oxidation of o-benzyl-N-methoxyl-benzamides when using Selectfluor as a hydrogen atom transfer (HAT) reagent and O-2 as oxidant. Efficient synthesis of a range of diversely functionalized 3-hydroxyisoindolinones can thus be achieved with good yields and selectivity at mild reaction conditions. Preliminary mechanistic studies and DFT calculations suggest that eosin Y works as a redox catalyst and photosensitizer.
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