| Autor: |
Lopes, José L., Baldassari, Lucas L., Lüdtke, Diogo S. |
| Předmět: |
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| Zdroj: |
New Journal of Chemistry; 1/21/2024, Vol. 48 Issue 3, p1164-1171, 8p |
| Abstrakt: |
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. [ABSTRACT FROM AUTHOR] |
| Databáze: |
Complementary Index |
| Externí odkaz: |
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