Carbon–carbon (C–C) bond formation is paramount in the synthesis of biologically relevant molecules, modern synthetic materials and commodity chemicals such as fuels and lubricants. Traditionally, the presence of a functional group is required at the site of C–C bond formation. Strategies that allow C–C bond formation at inert carbon–hydrogen (C–H) bonds enable access to molecules that would otherwise be inaccessible and the development of more efficient syntheses of complex molecules. Here we report a method for the formation of C–C bonds by directed cleavage of traditionally non-reactive C–H bonds and their subsequent coupling with readily available alkenes. Our methodology allows for amide-directed selective C–C bond formation at unactivated sp3 C–H bonds in molecules that contain many such bonds that are seemingly indistinguishable. Selectivity arises through a relayed photoredox-catalysed oxidation of a nitrogen–hydrogen bond. We anticipate that our findings will serve as a starting point for functionalization at inert C–H bonds through a strategy involving hydrogen-atom transfer.

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functionalization carbonhydrogen ch photoredoxcatalysed oxidation transfer selective cc bond formation

Tomislav Rovis,John C. K. Chu,.Amide-directed photoredox-catalysed C–C bond formation at unactivated sp3 C–H bonds. 2016 (10),.

Tomislav Rovis,John C. K. Chu,"Amide-directed photoredox-catalysed C–C bond formation at unactivated sp3 C–H bonds" 2016

Tomislav Rovis,John C. K. Chu,"Amide-directed photoredox-catalysed C–C bond formation at unactivated sp3 C–H bonds"