Enantioconvergent nucleophilic substitution via synergistic phase-transfer catalysis.

ABSTRACT: Catalytic enantioconvergent nucleophilic substitution reactions of alkyl halides are highly valuable transformations, but they are notoriously difficult to implement. Specifically, nucleophilic fluorination is a renowned challenge, especially when inexpensive alkali metal fluorides are used as fluorinating reagents due to their low solubility, high hygroscopicity and Brønsted basicity. Here we report a solution by developing the concept of synergistic hydrogen bonding phase-transfer catalysis. Key to our strategy is the combination of a chiral bis-urea hydrogen bond donor (HBD) and an onium salt-two phase-transfer catalysts essential for the solubilization of potassium fluoride-as a well-characterized ternary HBD-onium fluoride complex. Mechanistic investigations indicate that this

SUBMITTER: Dooley C 

PROVIDER: S-EPMC11860226 | biostudies-literature | 2025

REPOSITORIES: biostudies-literature