An unexpected reaction of 2-alkynylaryldiazonium tetrafluoroborate with sulfur dioxide?

Chemical Communications Pub Date: 2014-10-30 DOI: 10.1039/C4CC07938H

Abstract

An unexpected result from the reaction of 2-alkynylaryldiazonium tetrafluoroborate with sulfur dioxide is described. In the presence of morpholin-4-amine, this transformation catalyzed by copper(I) bromide proceeds through insertion of sulfur dioxide and intramolecular 5-endo cyclization, leading to benzo[b]thiophene 1,1-dioxides in moderate to good yields.

Graphical abstract: An unexpected reaction of 2-alkynylaryldiazonium tetrafluoroborate with sulfur dioxide
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