Nature research paper: Functional Group Translocation of Cyano Groups by Reversible C–H Sampling
Chemical transformations that introduce, remove, or manipulate functional groups are ubiquitous in synthetic chemistry.Unlike conventional FG interconversion reactions that swap one functionality for another, transformations that alterthe location of FGs are far less explored. Here, by photocatalytic, reversible C–H sampling, we report a FG translocation reaction of cyano groups in common nitriles, allowing for the direct positional exchange between a CN and an unactivated C−H bond.
The reaction shows high fidelity for 1,4-CN translocation, frequently contrary to inherent site selectivity in conventional C−H functionalizations. We also report the direct transannular CN translocation of cyclic systems, providing access to valuable structures that are non-trivial to obtain by other methods. Making use of the synthetic versatility of CN and a key CN translocation step, we showcase concise syntheses of building blocks of bioactive molecules.
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