General Light-Induced Pd-Catalyzed Allylic C–H Alkylation of Internal Alkenes: Direct Access to Tertiary and Quaternary Carbon Centers

Tertiary and quaternary carbon centers containing allylic systems are prevalent in natural products and drugs. Among existing approaches toward these valuable motifs, a direct allylic C-H alkylation is the most straightforward approach, which bypasses the requirement for prefunctionalization of allylic substrates. However, existing methods suffer from limited scope both in terms of alkenes and carbon nucleophiles. Herein, we report a light-induced Pd catalyzed method that overcomes these challenges, enabling the coupling of diverse internal alkenes with a range of carbon pronucleophiles including those with p<i>K</i><sub>a</sub> > 20. In addition, this method provides direct access to the construction of tertiary and quaternary carbon centers in enantioselective fashion.

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Publication Details

Journal
Journal of the American Chemical Society
Published
2025-11-13
DOI
https://doi.org/10.1021/jacs.5c15245
Citations
1
Primary Topic
Catalytic C–H Functionalization Methods
Type
article
Field-Weighted Citation Impact
0.94
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article

General Light-Induced Pd-Catalyzed Allylic C–H Alkylation of Internal Alkenes: Direct Access to Tertiary and Quaternary Carbon Centers

Vladimir Gevorgyan, Gaurav Prakash, Subham Pradhan
1 citations
Journal of the American Chemical Society
Catalytic C–H Functionalization Methods
0.94
article

General Light-Induced Pd-Catalyzed Allylic C–H Alkylation of Internal Alkenes: Direct Access to Tertiary and Quaternary Carbon Centers

Vladimir Gevorgyan, Gaurav Prakash, Subham Pradhan
article en
1 citations

Abstract

Tertiary and quaternary carbon centers containing allylic systems are prevalent in natural products and drugs. Among existing approaches toward these valuable motifs, a direct allylic C-H alkylation is the most straightforward approach, which bypasses the requirement for prefunctionalization of allylic substrates. However, existing methods suffer from limited scope both in terms of alkenes and carbon nucleophiles. Herein, we report a light-induced Pd catalyzed method that overcomes these challenges, enabling the coupling of diverse internal alkenes with a range of carbon pronucleophiles including those with p<i>K</i><sub>a</sub> > 20. In addition, this method provides direct access to the construction of tertiary and quaternary carbon centers in enantioselective fashion.

Journal of the American Chemical SocietyVol. 147(47)
The University of Texas at Dallas (US)
Openalex Percentile: Top 19%
Catalytic C–H Functionalization Methods
0.94
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