Photocatalytic α‐Tertiary Amine Synthesis via C–H Alkylation of Unmasked Primary Amines
- Alison S. H. Rydera
- William B. Cunninghamb
- George Ballantyneb
- Tom Mulesb
- Anna G. Kinsellab
- Jacob Turner-Doreb
- Catherine M. Alderc
- Lee J. Edwardsc
- Blandine S. J. McKayc
- Matthew N. Graysonb
- Alexander J. Cresswellb*
- aCentre for Sustainable Chemical Technologies, 1 South, University of Bath, Claverton Down, Bath, BA2 7AY (UK)
- bDepartment of Chemistry, 1 South, University of Bath, Claverton Down, Bath, BA2 7AY (UK)
- cMedicines Design, GSK Medicines Research Centre, Gunnels Wood Rd, Stevenage, SG1 2NY (UK)Read the publication that featured this abstract
A practical, catalytic entry to α,α,α‑trisubstituted (α‑tertiary) primary amines by C–H functionalisation has long been recognised as a critical gap in the synthetic toolbox. We report a simple and scalable solution to this problem that does not require any in situ protection of the amino group and proceeds with 100% atom‐economy. Our strategy, which uses an organic photocatalyst in combination with azide ion as a hydrogen atom transfer (HAT) catalyst, provides a direct synthesis of α‐tertiary amines, or their corresponding γ‑lactams. We anticipate that this methodology will inspire new retrosynthetic disconnections for substituted amine derivatives in organic synthesis, and particularly for challenging α‑tertiary primary amines.
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