Regiodivergent α- and β-Functionalization of Saturated N-Heterocycles by Photocatalytic Oxidation

07 May 2025, Version 1
This content is a preprint and has not undergone peer review at the time of posting.

Abstract

Synthetic methods that provide, via a central intermediate, access to two different types of products are highly valuable but difficult to establish. Here, we present a photocatalytic, regiodivergent method for the functionalization of saturated N-heterocycles at either the α- or the β-position. A t-butyl carbamate (Boc)-stabilized iminium ion serves as the key intermediate en route to either α-hydroxylation or β-elimination, depending on the choice of base. The operationally simple procedures use a readily available flavin-based catalyst and reagents, aqueous media, and do not require metals. Combined with facile downstream derivatization, the regiodivergent reaction gives rapid access to a large set of functionalized piperidines, molecules that are highly sought-after for the synthesis of pharmaceuticals and agrochemicals.

Supplementary materials

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Supporting Information
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Experimental details on the reactions including the analytical data of the presented compounds.
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