Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 136, Issue 16, Pages 6123-6135Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ja501988b
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Funding
- National Science Foundation [OCI-1053575, CHE-1059084]
- Alexander von Humboldt foundation
- Fonds der Chemischen Industrie
- German Academic Exchange Service
- NIH-NIGMS [R01GMI01389-01]
- Russian Federation [N2057]
- Direct For Mathematical & Physical Scien
- Division Of Chemistry [1059084] Funding Source: National Science Foundation
- Division Of Chemistry
- Direct For Mathematical & Physical Scien [1361104] Funding Source: National Science Foundation
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Cyclic secondary amines and 2-hydroxybenzaldehydes or related ketones react to furnish benzo[e][1,3]oxazine structures in generally good yields. This overall redox-neutral amine alpha-C--H functionalization features a combined reductive N-alkylation/oxidative alpha-functionalization and is catalyzed by acetic acid. In contrast to previous reports, no external oxidants or metal catalysts are required. Reactions performed under modified conditions lead to an apparent reductive amination and the formation of o-hydroxybenzylamines in a process that involves the oxidation of a second equivalent of amine. A detailed computational study employing density functional theory compares different mechanistic pathways and is used to explain the observed experimental findings. Furthermore, these results also reveal the origin of the catalytic efficiency of acetic acid in these transformations.
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