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Updated: Dec 22, 2025

Efficient Synthesis of Polyfunctionalized Benzenes in Water via Persulfate-promoted Benzannulation of α,β-Unsaturated Compounds and Alkynes
Published on: December 16, 2019
Trisubstituted Highly Activated Benzo[d]thiazol-2-yl-sulfone-Containing Olefins as Building Blocks in Organic
Ondřej Kováč1, František Zálešák1, David J-Y D Bon1
1Department of Organic Chemistry, Faculty of Science, Palacky University, tř. 17. listopadu 1192/12, CZ-771 46 Olomouc, Czech Republic.
Abstract:
In this paper, we report the formation of highly electrophilic 1,1-deactivated olefins, their use as novel synthetic building blocks, and their transformation to structurally diverse molecular scaffolds. Synthesis of 1,1-deactivated olefins substituted with a BT-sulfonyl group and a carbonyl or nitrile, respectively, consists of unusual Ti(OPr)4-mediated Knoevenagel-type condensation and proceed in good to excellent yields. Generated olefins can be further transformed in a highly stereoselective manner and in good yields to various polyfunctionalized heterocycles and acyclic molecular scaffolds. Overall, the obtained structures are accessed in two to four steps starting from the (mostly) commercially available aldehydes. In addition, the presence of the BT-sulfonyl group in prepared structures allows for further chemoselective functionalization/post-synthetic transformations to provide structurally diverse final compounds.
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