Amide-directed photoredox-catalysed C–C bond formation at unactivated sp3 C–H bonds
| Autor: | John C. K. Chu, Tomislav Rovis |
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| Rok vydání: | 2016 |
| Předmět: |
Multidisciplinary
Mechanical bond 010405 organic chemistry Stereochemistry 010402 general chemistry Cleavage (embryo) 01 natural sciences Combinatorial chemistry 0104 chemical sciences chemistry.chemical_compound chemistry Amide Functional group Molecule Surface modification Selectivity Bond cleavage |
| Zdroj: | Nature. 539:272-275 |
| ISSN: | 1476-4687 0028-0836 |
| DOI: | 10.1038/nature19810 |
| Popis: | 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. |
| Databáze: | OpenAIRE |
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