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Issue 77, 2017
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A tandem annulation with a [1,3]-hydride transfer as the key step leading to isochromans

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Abstract

An unprecedented method that enables the direct coupling of an α-C–H bond in alcohols with 2-arylacetaldehydes through a [1,3]-hydride transfer ([1,3]-HT) of oxocarbenium ions catalyzed by a Lewis acid has been developed. The redox neutral preparation of the isochroman derivatives proceeds via a tandem condensation/[1,3]-HT/Friedel–Crafts sequence with moderate to good yields. Deuterium-labeling studies provide mechanistic insights and reveal that the redox functionalization proceeds via a [1,3]-HT.

Graphical abstract: A tandem annulation with a [1,3]-hydride transfer as the key step leading to isochromans

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Publication details

The article was received on 09 Aug 2017, accepted on 30 Aug 2017 and first published on 01 Sep 2017


Article type: Communication
DOI: 10.1039/C7CC06144G
Citation: Chem. Commun., 2017,53, 10652-10655
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    A tandem annulation with a [1,3]-hydride transfer as the key step leading to isochromans

    Y. Wang, G. Li, H. Liu, Z. Tang, Y. Cao and G. Zhao, Chem. Commun., 2017, 53, 10652
    DOI: 10.1039/C7CC06144G

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