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

Organic Chemistry Frontiers Pub Date: 2016-03-21 DOI: 10.1039/C6QO00070C

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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