Litcius/Paper detail

Direct C–H Allylation of Unactivated Alkanes by Cooperative W/Cu Photocatalysis

Pol Martínez-Balart, Balázs L. Tóth, Álvaro Velasco‐Rubio, Martín Fañanás‐Mastral

2022Organic Letters21 citationsDOIOpen Access PDF

Abstract

Here we report a photocatalytic methodology that enables the direct allylation of strong aliphatic C–H bonds with simple allylic chlorides. The method relies on a cooperative interaction of two metal catalysts in which the decatungstate anion acts as a hydrogen-atom abstractor generating a nucleophilic carbon-centered radical that engages in an SH2′ reaction with an activated allylic π-olefin–copper complex. Because of this dual catalysis, the protocol allows for the functionalization of a range of chemical feedstocks and natural products under mild conditions in short reaction times.

Topics & Concepts

ChemistryPhotocatalysisCombinatorial chemistryMedicinal chemistryCatalysisStereochemistryOrganic chemistryCatalytic C–H Functionalization MethodsRadical Photochemical ReactionsSulfur-Based Synthesis Techniques