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

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

Research output: Contribution to journalArticle

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.

Original languageEnglish
JournalAngewandte Chemie (International ed. in English)
Early online date11 Jun 2020
DOIs
Publication statusE-pub ahead of print - 11 Jun 2020

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