Figure - available from: Nature Catalysis
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Enantioconvergent approaches for nucleophilic substitution a, Nucleophilic substitution via SN1, SN2, SN2X, transition metal-catalysed and photoredox mechanisms. b, HBPTC for the desymmetrization of meso-onium-type electrophiles with alkali metal fluoride salts (MF). c, S-HBPTC (this work): enantioconvergent nucleophilic substitution of benzylic bromides and α-haloketones with KF and two phase-transfer catalysts (a chiral HBD and an achiral onium salt). hv, visible light; cat*, chiral catalyst; DKR, dynamic kinetic resolution; TMS, trimethylsilyl; Nu, nucleophile; LG, leaving group.
Source publication
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...
