- Photocatalytic α-Tertiary Amine Synthesis via C?H Alkylation of Unmasked Primary Amines
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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 percent 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.
- Alder, Catherine M.,Ballantyne, George,Cresswell, Alexander J.,Cunningham, William B.,Edwards, Lee J.,Grayson, Matthew N.,Kinsella, Anna G.,McKay, Blandine S. J.,Mules, Tom,Ryder, Alison S. H.,Turner-Dore, Jacob
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p. 14986 - 14991
(2020/06/20)
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