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Issue 19, 2018
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Thiyl radical promoted chemo- and regioselective oxidation of C[double bond, length as m-dash]C bonds using molecular oxygen via iron catalysis

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Abstract

The first example of the thiyl radical promoted ligand-free iron-catalyzed oxidative cleavage of alkenes using molecular oxygen (1 atm) has been developed. The reaction proceeds under mild reaction conditions with high efficiency and high chemo- and regioselectivity. It features a broad substrate scope and excellent functional group compatibility, enabling facile access to valuable molecules for application in medicinal chemistry. Preliminary mechanistic studies reveal that a vital intermediate dioxetane might be involved in the reaction and a thiyl radical plays a synergistic role in facilitating the selective oxidation of the C[double bond, length as m-dash]C bond.

Graphical abstract: Thiyl radical promoted chemo- and regioselective oxidation of C [[double bond, length as m-dash]] C bonds using molecular oxygen via iron catalysis

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Publication details

The article was received on 29 Jul 2018, accepted on 31 Aug 2018 and first published on 31 Aug 2018


Article type: Paper
DOI: 10.1039/C8GC02369G
Green Chem., 2018,20, 4521-4527

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    Thiyl radical promoted chemo- and regioselective oxidation of C[double bond, length as m-dash]C bonds using molecular oxygen via iron catalysis

    B. Xiong, X. Zeng, S. Geng, S. Chen, Y. He and Z. Feng, Green Chem., 2018, 20, 4521
    DOI: 10.1039/C8GC02369G

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