Iron-catalyzed fluoroalkylative alkylsulfonylation of alkenes via radical-anion relay

Xiaoya Hou, Hongchi Liu and Hanmin Huang ()
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Xiaoya Hou: University of Science and Technology of China
Hongchi Liu: University of Science and Technology of China
Hanmin Huang: University of Science and Technology of China

Nature Communications, 2024, vol. 15, issue 1, 1-9

Abstract: Abstract Transition metal-catalyzed reductive difunctionalization of alkenes with alkyl halides is a powerful method for upgrading commodity chemicals into densely functionalized molecules. However, super stoichiometric amounts of metal reductant and the requirement of installing a directing group into alkenes to suppress the inherent β-H elimination bring great limitations to this type of reaction. We demonstrate herein that the difunctionalization of alkenes with two different alkyl halides is accessible via a radical-anion relay with Na2S2O4 as both reductant and sulfone-source. The Na2S2O4 together with the electron-shuttle catalyst is crucial to divert the mechanistic pathway toward the formation of alkyl sulfone anion instead of the previously reported alkylmetal intermediates. Mechanistic studies allow the identification of carbon-centered alkyl radical and sulfur-centered alkyl sulfone radical, which are in equilibrium via capture or extrusion of SO2 and could be converted to alkyl sulfone anion accelerated by iron electron-shuttle catalysis, leading to the observed high chemoselectivity.

Date: 2024
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DOI: 10.1038/s41467-024-45867-y

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