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Updated: Apr 23, 2026

Facile Preparation of 2Z,4E-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
Published on: June 21, 2017
HFIP-Promoted PdH-Electrocatalytic Remote Ritter-Type Hydrofunctionalization of Alkenes: Divergent Access to Amides
Seungdae Park1, Taehwan Kim1, Junhyeon Choi1
1Department of Chemistry, Sungkyunkwan University, Suwon 16419, Republic of Korea.
This study introduces a novel electrooxidative palladium-hydride-catalyzed Ritter-type reaction for alkenes. The method enables remote C(sp3)-N bond formation and divergent synthesis of valuable nitrogen-containing compounds.
Area of Science:
- Organic Chemistry
- Catalysis
- Synthetic Methodology
Background:
- Ritter-type hydrofunctionalization is key for C(sp3)-N bond formation but typically limited to the alkene position.
- Existing methods lack remote functionalization and divergent synthetic capabilities.
Purpose of the Study:
- To develop a novel electrooxidative palladium-hydride-catalyzed remote Ritter-type hydrofunctionalization of alkenes.
- To achieve divergent synthesis of nitrogen-containing compounds via telescoped reactions.
Main Methods:
- Utilized an electrooxidative palladium-hydride catalytic system.
- Employed 1,1,1,3,3,3-hexafluoro-2-propanol (HFIP) as a trapping agent for distal nitrilium intermediates.
- Investigated mechanistic pathways using mechanistic studies.
Main Results:
- Successfully achieved remote Ritter-type hydrofunctionalization of alkenes.
- Generated a HFIP-derived imidate intermediate for divergent synthesis.
- Demonstrated telescoped remote hydroamidation and hydrotetrazolation.
Conclusions:
- The developed catalytic system enables efficient remote C(sp3)-N bond construction.
- HFIP plays a crucial role in facilitating palladium-hydride formation and intermediate generation.
- Electrooxidation is vital for controlling product outcomes in this divergent synthesis.
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