Photocatalytic α‐Tertiary Amine Synthesis via C−H Alkylation of Unmasked Primary Amines

Abtract

A) Prior art for catalytic α‐C−H alkylation of primary amines; B) This work. EWG=electron‐withdrawing group.

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.

Authors: Alison S. H. Ryder Dr. William B. Cunningham George Ballantyne Tom Mules Anna G. Kinsella Jacob Turner‐Dore Dr. Catherine M. Alder Lee J. Edwards Dr. Blandine S. J. McKay Dr. Matthew N. Grayson Dr. Alexander J. Cresswell

Link
https://onlinelibrary.wiley.com/doi/full/10.1002/anie.202005294#.Xr2aciKIkvU.twitter

 

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