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- Title
Reshuffle Bonds by Ball Milling: A Mechanochemical Protocol for Charge-Accelerated Aza-Claisen Rearrangements.
- Authors
Schumacher, Christian; Fritz, Lieselotte; Hanek, Lena M.; Sidorin, Vitali; Brüx, Daniel; Bolm, Carsten
- Abstract
This study presents the development of a mechanochemical protocol for a charge-accelerated aza-Claisen rearrangement. The protocol waives the use of commonly applied transition metals, ligands, or pyrophoric Lewis acids, e.g., AlMe3. Based on (heterocyclic) tertiary allylamines and acyl chlorides, the desired tertiary amides were prepared in yields ranging from 17% to 84%. Moreover, the same protocol was applied for a Belluš–Claisen-type rearrangement resulting in the synthesis of a 9-membered lactam without further optimization.
- Subjects
BALL mills; LEWIS acids; TRANSITION metals; ACYL chlorides; ALLYLAMINES; AMIDES
- Publication
Molecules, 2023, Vol 28, Issue 2, p807
- ISSN
1420-3049
- Publication type
Article
- DOI
10.3390/molecules28020807