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Updated: Mar 31, 2026

A Two-Step Protocol for Umpolung Functionalization of Ketones Via Enolonium Species
Published on: August 16, 2018
Potassium tert-Butoxide-Mediated Isomerization of Alkenes: A Versatile Protocol for Miscellaneous Substrates
Héctor Mario Heras Martínez1, Sydney M Hampton1, Stephen R Isbel1
1Department of Chemistry and Physics, Florida Gulf Coast University, Fort Myers, Florida 33965, United States.
Abstract:
The development of rapid and efficient routes to alkene derivatives remains a significant priority due to their broad utility as building blocks and valuable compounds. Herein, we report a simple, general, and highly efficient procedure for the (catalytic) isomerization of alkenes under mild conditions. This method is applicable to a wide range of substrates, including allylic derivatives of benzenes, aromatic and aliphatic systems, heterocycles, ethers, thioethers, amines, and sulfones. In this transformation, KO t Bu acts as both the base and the proton shuttle, enabling the reaction to proceed under air and affording quantitative yields within minutes for the majority of the substrates examined. The reaction occurs under thermodynamic control, affording the most stable isomer (typically, the E-alkene).
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