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Issue 10, 2018
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Direct cross-coupling between alkenes and tetrahydrofuran with a platinum-loaded titanium oxide photocatalyst

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Abstract

A Pt-loaded TiO2 photocatalyst successfully catalyzed the direct cross-coupling between various alkenes and tetrahydrofuran (THF) without any additional oxidizing agent. The reaction between cyclohexene and THF gave three cross-coupling products, namely, 2-cyclohexyltetrahydrofuran (A), 2-(cyclohex-2-en-1-yl)tetrahydrofuran (B) and 2-(cyclohex-1-en-1-yl)tetrahydrofuran (C), along with gaseous hydrogen. The mechanistic study revealed that these products were formed through different individual mechanisms: successive addition of two radical species, a 2-tetrahydrofuranyl radical and a hydrogen radical, to the double bond of cyclohexene for A, coupling of a 3-cyclohexenyl radical and a 2-tetrahydrofuranyl radical for B, and 2-tetrahydrofuranyl radical addition and hydrogen radical elimination at the double bond of cyclohexene for C. Among these three mechanisms, those for B and C are dehydrogenative. In this photocatalytic reaction system, since the cyclohexene molecule has enough reactivity, due to the localized π electron density, the Pt nanoparticles loaded on the TiO2 function not as a metal catalyst but as an electron receiver to enhance the charge separation, although the dehydrogenative cross-coupling of benzene with THF requires Pd metal catalysis.

Graphical abstract: Direct cross-coupling between alkenes and tetrahydrofuran with a platinum-loaded titanium oxide photocatalyst

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Publication details

The article was received on 20 Jan 2018, accepted on 25 Mar 2018 and first published on 26 Mar 2018


Article type: Paper
DOI: 10.1039/C8CY00129D
Citation: Catal. Sci. Technol., 2018,8, 2546-2556
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    Direct cross-coupling between alkenes and tetrahydrofuran with a platinum-loaded titanium oxide photocatalyst

    A. Tyagi, A. Yamamoto, M. Yamamoto, T. Yoshida and H. Yoshida, Catal. Sci. Technol., 2018, 8, 2546
    DOI: 10.1039/C8CY00129D

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