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Issue 6, 2019
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I2/DMSO-mediated multicomponent reaction of o-hydroxyaryl methyl ketones, rongalite, and DMSO: access to C3-sulfenylated chromones

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Abstract

An efficient I2–DMSO reagent system-mediated multicomponent reaction strategy for the synthesis of C3-sulfenylated chromones from o-hydroxyaryl methyl ketones, rongalite, and dimethyl sulfoxide has been developed. Notably, the double C–S bond cleavages of rongalite and dimethyl sulfoxide served as key steps in this smooth transformation, affording the C1 unit and sulfur source for the assembly of C3-sulfenylated chromones. Preliminary mechanistic studies indicated that in situ generated HCHO and (2-(2-hydroxyphenyl)-2-oxoethyl)dimethylsulfonium iodine were probably the key intermediates in this transformation.

Graphical abstract: I2/DMSO-mediated multicomponent reaction of o-hydroxyaryl methyl ketones, rongalite, and DMSO: access to C3-sulfenylated chromones

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Publication details

The article was received on 01 Dec 2018, accepted on 16 Jan 2019 and first published on 16 Jan 2019


Article type: Paper
DOI: 10.1039/C8OB02994F
Citation: Org. Biomol. Chem., 2019,17, 1535-1541

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    I2/DMSO-mediated multicomponent reaction of o-hydroxyaryl methyl ketones, rongalite, and DMSO: access to C3-sulfenylated chromones

    M. Wang, B. Tang, J. Ma, Z. Wang, J. Xiang, Y. Wu, J. Wang and A. Wu, Org. Biomol. Chem., 2019, 17, 1535
    DOI: 10.1039/C8OB02994F

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