Silver(i)-catalyzed stereoselective Meyer–Schuster-type rearrangement: synthesis of densely substituted α-iodo α,β-unsaturated thioesters
Literature Information
Publication Date
2023-12-07
DOI
10.1039/D3NJ05144G
Impact Factor
3.591
Authors
José L. Lopes, Lucas L. Baldassari, Diogo S. Lüdtke
View Original
Abstract
Herein, we report our approach for a Meyer–Schuster type rearrangement to access α-iodo α,β-unsaturated thioesters from propargyl thioalkynes using a silver(I) catalyst and N-iodosuccinimide as an electrophilic iodine source. The reaction proceeds smoothly for a range of propargyl thioalkynes, thus delivering tri- and tetrasubstituted olefins in good yields and, for a number of examples, (Z)-selectivity. The silver catalyst presumably plays a dual role involving both the activation of the π-system by the alkynophilic Ag(I) and the activation of the NIS, ultimately leading to a sulfur-stabilized vinyl cation/ketenethionium intermediate. This reactive intermediate is trapped intramolecularly to yield an oxetane, which then readily undergoes decomposition to deliver the final product.
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New Journal of Chemistry
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