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Generation of benzosultams via a radical process with the insertion of sulfur dioxide

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Abstract

An efficient route to diverse 3-sulfonated-2,3-dihydrobenzo[d]isothiazole 1,1-dioxides is achieved through a three-component reaction of 2-ethynylbenzenesulfonamides, DABCO-bis(sulfur dioxide), and aryldiazonium tetrafluoroborates. The corresponding sulfonated benzosultams are produced in moderate to good yields. During the reaction process, the in situ generated arylsulfonyl radical via addition of an aryl radical to sulfur dioxide and the subsequent single electron transfer would be the key steps for the final outcome. DABCO acts as the carrier for single electron transfer, as well as a base to promote the C–N bond formation.

Graphical abstract: Generation of benzosultams via a radical process with the insertion of sulfur dioxide

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Publication details

The article was received on 15 Feb 2017, accepted on 01 Mar 2017 and first published on 02 Mar 2017


Article type: Research Article
DOI: 10.1039/C7QO00127D
Citation: Org. Chem. Front., 2017, Advance Article
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    Generation of benzosultams via a radical process with the insertion of sulfur dioxide

    K. Zhou, H. Xia and J. Wu, Org. Chem. Front., 2017, Advance Article , DOI: 10.1039/C7QO00127D

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