Nickel-Catalyzed Alkenylation of N-Heteroarenes with Fluorinated Alcohols: Direct Access to CF <sub>3</sub> -Embedded Olefins

Herein, a sequential Ni-catalyzed acceptorless dehydrogenation followed by condensation of bench-stable fluorinated alcohols with 2-oxindoles or methyl N-heteroarenes to CF<sub>3</sub>-embedded olefins is reported. The protocol is tolerant to a series of 2-oxindoles, methyl azaarenes, and primary and secondary fluorinated alcohols, and the late-stage functionalization of a vitamin derivative is a key highlight (>21 examples and up to 89% yield). Preliminary mechanistic studies and control experiments were performed to understand the reaction pathways.

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Publication Details

Journal
Organic Letters
Published
2025-12-30
DOI
https://doi.org/10.1021/acs.orglett.5c05007
Primary Topic
Fluorine in Organic Chemistry
Type
article
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article

Nickel-Catalyzed Alkenylation of N-Heteroarenes with Fluorinated Alcohols: Direct Access to CF 3 -Embedded Olefins

Shuvojit Haldar, Adrija Ghosh, Purushotam, Debasis Banerjee et al.
Organic Letters
Fluorine in Organic Chemistry
article

Nickel-Catalyzed Alkenylation of N-Heteroarenes with Fluorinated Alcohols: Direct Access to CF 3 -Embedded Olefins

Shuvojit Haldar, Adrija Ghosh, Purushotam, Debasis Banerjee, Atanu Bera
article en

Abstract

Herein, a sequential Ni-catalyzed acceptorless dehydrogenation followed by condensation of bench-stable fluorinated alcohols with 2-oxindoles or methyl N-heteroarenes to CF<sub>3</sub>-embedded olefins is reported. The protocol is tolerant to a series of 2-oxindoles, methyl azaarenes, and primary and secondary fluorinated alcohols, and the late-stage functionalization of a vitamin derivative is a key highlight (>21 examples and up to 89% yield). Preliminary mechanistic studies and control experiments were performed to understand the reaction pathways.

Organic LettersVol. 28(1)
Indian Institute of Technology Roorkee (IN), Institute of Organic Synthesis (RU), Laboratoire de Synthèse Organique (FR), Chemical Synthesis Lab (SG)
Openalex Percentile: Top 36%
Fluorine in Organic Chemistry
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