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Issue 33, 2019
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Iron-catalyzed oxidative C–C(vinyl) σ-bond cleavage of allylarenes to aryl aldehydes at room temperature with ambient air

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Abstract

A general and selective iron-catalyzed allylic C–C(vinyl) σ-bond cleavage of allylarenes without the assistance of heteroatoms to give aryl aldehydes is reported. The unstrained carbon–carbon single bond cleavage reaction uses ambient air as the sole oxidant, proceeds efficiently at room temperature, and allows for exceptional functional-group tolerance, which addresses the long-standing challenges of current C–C bond cleavage/functionalization. Notably, the method enables rapid late-stage oxidation of complex bioactive molecules and can be used to expedite syntheses of natural products (vanillin and glucovanillin) from readily available chemical feedstocks.

Graphical abstract: Iron-catalyzed oxidative C–C(vinyl) σ-bond cleavage of allylarenes to aryl aldehydes at room temperature with ambient air

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Publication details

The article was received on 13 Mar 2019, accepted on 28 Mar 2019 and first published on 28 Mar 2019


Article type: Communication
DOI: 10.1039/C9CC01995B
Chem. Commun., 2019,55, 4817-4820

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    Iron-catalyzed oxidative C–C(vinyl) σ-bond cleavage of allylarenes to aryl aldehydes at room temperature with ambient air

    B. Liu, L. Cheng, P. Hu, F. Xu, D. Li, W. Gu and W. Han, Chem. Commun., 2019, 55, 4817
    DOI: 10.1039/C9CC01995B

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