AI Article Synopsis
- - The presence of a heteroatom in an aromatic ring affects the compound's chemical properties, but swapping atoms in these structures can be challenging due to thermodynamic issues.
- - A new photocatalytic method has been developed to replace an oxygen atom in furan with a nitrogen group, converting it into a pyrrole derivative in one step.
- - This method works well with different furan derivatives and nitrogen sources used in drug discovery, and it allows for the functionalization of complex naturally occurring furans into useful pyrroles, with a mechanism based on polarity inversion from single electron transfer.
Article Abstract
The identity of a heteroatom within an aromatic ring influences the chemical properties of that heterocyclic compound. Systematically evaluating the effect of a single atom, however, poses synthetic challenges, primarily as a result of thermodynamic mismatches in atomic exchange processes. We present a photocatalytic strategy that swaps an oxygen atom of furan with a nitrogen group, directly converting the furan into a pyrrole analog in a single intermolecular reaction. High compatibility was observed with various furan derivatives and nitrogen nucleophiles commonly used in drug discovery, and the late-stage functionalization furnished otherwise difficult-to-access pyrroles from naturally occurring furans of high molecular complexity. Mechanistic analysis suggested that polarity inversion through single electron transfer initiates the redox-neutral atom exchange processes at room temperature.
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| http://dx.doi.org/10.1126/science.adq6245 | DOI Listing |
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