Reprogramming alkylamine reactivity for direct C–C bond formation

Event Details

Dr Alexander Cresswell from the University of Bath joins us for a seminar on alkylamine reactivity for direct C–C bond formation. Also on Microsoft Teams.

Abstract

We have uncovered a new mode of reactivity for unprotected alkylamines, enabling them to participate in direct C–C bond formation as carbon nucleophiles, rather than conventional nitrogen nucleophiles. This conceptually distinct strategy for amine synthesis, enabled by the merger of photoredox and hydrogen atom transfer (HAT) catalysis, provides rapid access to α‑tertiary and spirocyclic amine architectures through selective α-C–H functionalisation. The process is readily translated to automated and continuous-flow platforms, offering a scalable route to structurally complex amines with broad potential for application in medicinal chemistry and drug discovery.

References:

[1] “Scalable Photocatalytic Annulation of Primary Amines to δ-Lactams: Access to Privileged (Spiro)Piperidine Space” Org. Lett. 2026, 28, 9603.

[2] “Direct α-C−H Heteroarylation of Unprotected Primary Amines” ACS Catal. 2026, 16, 10290.

[3] “Modular, Automated Synthesis of Spirocyclic Tetrahydronaphthyridines from Primary Alkylamines” Commun. Chem. 2023, 6, 215.

[4] “Photocatalytic Hydroaminoalkylation of Styrenes with Unprotected Primary Alkylamines” J. Am. Chem. Soc. 2021, 143, 15936

[5] “Photocatalytic α‐Tertiary Amine Synthesis via C−H Alkylation of Unmasked Primary Amines” Angew. Chem. Int. Ed. 2020, 59, 14986.

For the Teams link, please contact the organiser.