Ni‐Catalyzed Cross‐Electrophile Couplings of <i>N</i>‐Alkoxyphthalimides and Aryl Halides

N ‐alkoxyphthalimides represent a versatile class of redox‐active alcohol derivatives for carbon–carbon bond formation following activation by single‐electron reduction. Herein, key precedents using N ‐alkoxyphthalimides for the formation of new carbon–carbon bonds under photochemical reaction conditions are first presented. The merger of these and other single‐electron activation strategies with Ni catalysis in various cross‐electrophile couplings with aryl halides is then highlighted. A particular focus is made on the mechanisms proposed for these Ni‐catalyzed reductive cross‐couplings. Concluding thoughts for future reaction design using N ‐alkoxyphthalimides as redox‐active C(sp 3 )O derivatives in transition metal‐catalyzed cross‐couplings are also presented.

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Publication Details

Journal
European Journal of Organic Chemistry
Published
2025-04-13
DOI
https://doi.org/10.1002/ejoc.202500122
Primary Topic
Catalytic C–H Functionalization Methods
Type
article
Field-Weighted Citation Impact
0.00

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article

Ni‐Catalyzed Cross‐Electrophile Couplings of N‐Alkoxyphthalimides and Aryl Halides

John J. Monteith, Sophie A. L. Rousseaux
European Journal of Organic Chemistry
Catalytic C–H Functionalization Methods
article

Ni‐Catalyzed Cross‐Electrophile Couplings of N‐Alkoxyphthalimides and Aryl Halides

John J. Monteith, Sophie A. L. Rousseaux
article en

Abstract

N ‐alkoxyphthalimides represent a versatile class of redox‐active alcohol derivatives for carbon–carbon bond formation following activation by single‐electron reduction. Herein, key precedents using N ‐alkoxyphthalimides for the formation of new carbon–carbon bonds under photochemical reaction conditions are first presented. The merger of these and other single‐electron activation strategies with Ni catalysis in various cross‐electrophile couplings with aryl halides is then highlighted. A particular focus is made on the mechanisms proposed for these Ni‐catalyzed reductive cross‐couplings. Concluding thoughts for future reaction design using N ‐alkoxyphthalimides as redox‐active C(sp 3 )O derivatives in transition metal‐catalyzed cross‐couplings are also presented.

European Journal of Organic ChemistryVol. 28(20)
University of Toronto (CA)
Alfred P. Sloan Foundation, Canada Foundation for Innovation, University of Toronto, Natural Sciences and Engineering Research Council of Canada
Openalex Percentile: Top 94%
Catalytic C–H Functionalization Methods
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