Alkylation of Allyl/Alkenyl Sulfones by Deoxygenation of Alkoxyl Radicals

Chemistry. 2019 Feb 26;25(12):2989-2994. doi: 10.1002/chem.201806138. Epub 2019 Jan 29.

Abstract

A challenging deoxygenation of alkoxyl radicals from readily accessible alcohol derivatives was developed, affording facile synthesis of functionalized alkenes with good functional group tolerance under mild reaction conditions. Because alkoxyl radicals can easily undergo β-fragmentations or hydrogen abstractions, this new strategy for deoxygenation of alkoxyl radicals is highly valuable. Moreover, mechanistic studies revealed that the electron-neutral phosphine acts as the deoxygenation reagent.

Keywords: alkenes; alkoxyl radical; deoxygenation; photoredox catalysis; radical alkylation.