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Issue 6, 2016
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Copper(i)-catalyzed sulfonylation of (2-alkynylaryl)boronic acids with DABSO

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Abstract

The scaffold of benzo[b]thiophene 1,1-dioxides can be easily constructed through a copper(I)-catalyzed insertion of sulfur dioxide into (2-alkynylaryl)boronic acids. The reaction proceeds in the presence of 10 mol% copper(I) acetate in DMF at 100 °C with high efficiency, leading to benzo[b]thiophene 1,1-dioxides in good to excellent yields. The sulfonyl group can be easily introduced via insertion of sulfur dioxide and the subsequent intramolecular 5-endo cyclization affords the core of benzo[b]thiophene 1,1-dioxide.

Graphical abstract: Copper(i)-catalyzed sulfonylation of (2-alkynylaryl)boronic acids with DABSO

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Supplementary files

Article information


Submitted
17 Feb 2016
Accepted
19 Mar 2016
First published
21 Mar 2016

Org. Chem. Front., 2016,3, 693-696
Article type
Research Article

Copper(I)-catalyzed sulfonylation of (2-alkynylaryl)boronic acids with DABSO

R. Mao, D. Zheng, H. Xia and J. Wu, Org. Chem. Front., 2016, 3, 693
DOI: 10.1039/C6QO00070C

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