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Regioselective α-Phosphonylation of Unprotected Alicyclic Amines.

Bowen LiFu-Chao YuWeijie ChenDaniel Seidel
Published in: Organic letters (2024)
Unprotected alicyclic amines undergo α-C-H bond phosphonylation via a two-stage one-pot process involving the oxidation of amine-derived lithium amides with simple ketone oxidants, generating transient imines which are then captured with phosphites or phosphine oxides. Amines with an existing α-substituent undergo regioselective α'-phosphonylation. Amine α-arylation and α'-phosphonylation can be combined, generating a difunctionalized product in a single operation.
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