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Issue 13, 2018
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Homodimerization of 2H-chromenes catalyzed by Brønsted-acid derived UiO-66 MOFs

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Abstract

Two UiO-66 derived Brønsted acid metal–organic framework (MOF) catalysts were prepared through a facile post-synthetic modification method, characterized by SEM, XRD, 1H NMR, FTIR, BET and TGA and applied as heterogeneous catalysts in the homodimerization of 2H-chromenes. Several substituted tetrahydrochromeno heterocycles were generated in high yields, at reduced reaction times and with good diastereoselectivities, taking advantage of the strong Brønsted-acidic sites. A detailed mechanism was proposed and a tandem rearrangement/hetero-Diels–Alder reaction sequence was revealed. Deuterium labeling and various dienophiles were studied to verify the hypothesis of a pathway based on a hydride shift followed by ortho-quinone methide cycloaddition.

Graphical abstract: Homodimerization of 2H-chromenes catalyzed by Brønsted-acid derived UiO-66 MOFs

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Publication details

The article was received on 20 Nov 2017, accepted on 01 Jun 2018 and first published on 06 Jun 2018


Article type: Paper
DOI: 10.1039/C7CY02362F
Citation: Catal. Sci. Technol., 2018,8, 3406-3413
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    Homodimerization of 2H-chromenes catalyzed by Brønsted-acid derived UiO-66 MOFs

    Z. Miao, Z. Zhou, H. Tang, M. Yu, D. Ramella, X. Du and Y. Luan, Catal. Sci. Technol., 2018, 8, 3406
    DOI: 10.1039/C7CY02362F

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