HFIP-Promoted PdH-Electrocatalytic Remote Ritter-Type Hydrofunctionalization of Alkenes: Divergent Access to Amides and Tetrazoles

)-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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Journal
Organic Letters
Published
2026-04-21
DOI
https://doi.org/10.1021/acs.orglett.6c01243
Primary Topic
Catalytic C–H Functionalization Methods
Type
article
Field-Weighted Citation Impact
0.00

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article

HFIP-Promoted PdH-Electrocatalytic Remote Ritter-Type Hydrofunctionalization of Alkenes: Divergent Access to Amides and Tetrazoles

Kwangmin Shin, Junhyeon Choi, Seungdae Park, Do Hyun Ryu et al.
Organic Letters
Catalytic C–H Functionalization Methods
article

HFIP-Promoted PdH-Electrocatalytic Remote Ritter-Type Hydrofunctionalization of Alkenes: Divergent Access to Amides and Tetrazoles

Kwangmin Shin, Junhyeon Choi, Seungdae Park, Do Hyun Ryu, Taehwan Kim
article en

Abstract

)-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.

Organic LettersVol. 28(17)
Sungkyunkwan University (KR)
Korea Basic Science Institute, National Research Foundation of Korea
Openalex Percentile: Top 20%
Catalytic C–H Functionalization Methods
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