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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.
Abstract:
Ritter-type hydrofunctionalization of alkenes provides an efficient approach for constructing C(sp3)-N bonds, but it is generally limited to amide installation at original alkene position. Herein, we report an electrooxidative palladium-hydride-catalyzed remote and divergent Ritter-type hydrofunctionalization of alkenes. In this catalytic system, a nitrilium intermediate generated at a distal position is intercepted by HFIP to furnish a HFIP-derived imidate, which serves as a branching intermediate for telescoped remote hydroamidation and hydrotetrazolation. Mechanistic studies elucidate that HFIP facilitates palladium-hydride formation, and further reveal the role of electrooxidation in governing product formation.
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