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Updated: May 23, 2025
Facile Preparation of 2Z,4E-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
Published on: June 21, 2017
Mild Hydroalkylation of Terminal Olefins Via Decatungstate/Thiol Cooperative Photocatalysis
Austin J Moser1, Paige E Sutter1, Alex M Chavez1
1Department of Chemistry, Rice University, 6500 Main Street, Houston, Texas 77005, United States.
Abstract:
Here we report the use of a tetrabutylammonium decatungstate (TBADT)/thiol photocatalytic system for selective addition of acetone and other simple ketone, nitrile, and chlorocarbon functionalities to terminal olefins. This system avoids the use of energetic reagents such as peroxides and proceeds under mild conditions using Earth-abundant element catalysts, providing a sustainable approach to C-C bond formation using activated olefins. Initial exploration reveals that hydroalkylation of unactivated olefins is also possible, though in lower efficiency, and preliminary mechanistic experiments are consistent with a radical mechanism.
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