α-Arylation of Glutarimides via Ni/Ir Metallaphotoredox Cross-Electrophile Coupling

Herein, we report a photochemical Ni-catalyzed cross-electrophile coupling of an α-mesylate glutarimide with aryl bromides to access 22 examples of α-arylglutarimides. Mechanistic insights allowed for the additional development of conditions that utilize a commercially available α-bromoglutarimide as a substitute for the α-mesylate glutarimide via a slow-addition protocol. These methods employ visible-light-driven metallaphotoredox catalysis to efficiently synthesize key scaffolds utilized in targeted protein degradation therapies.

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Publication Details

Journal
The Journal of Organic Chemistry
Published
2026-02-23
DOI
https://doi.org/10.1021/acs.joc.5c03122
Primary Topic
Catalytic Cross-Coupling Reactions
Type
article
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article

α-Arylation of Glutarimides via Ni/Ir Metallaphotoredox Cross-Electrophile Coupling

Dustin A. Bringley, Mareena C. Franke, Erin L. Kuker, Michael A. Ischay
The Journal of Organic Chemistry
Catalytic Cross-Coupling Reactions
article

α-Arylation of Glutarimides via Ni/Ir Metallaphotoredox Cross-Electrophile Coupling

Dustin A. Bringley, Mareena C. Franke, Erin L. Kuker, Michael A. Ischay
article en

Abstract

Herein, we report a photochemical Ni-catalyzed cross-electrophile coupling of an α-mesylate glutarimide with aryl bromides to access 22 examples of α-arylglutarimides. Mechanistic insights allowed for the additional development of conditions that utilize a commercially available α-bromoglutarimide as a substitute for the α-mesylate glutarimide via a slow-addition protocol. These methods employ visible-light-driven metallaphotoredox catalysis to efficiently synthesize key scaffolds utilized in targeted protein degradation therapies.

The Journal of Organic ChemistryVol. 91(9)
Institute of Process Engineering (CN), Gilead Sciences (United States) (US), Gilead Sciences (France) (FR)
Openalex Percentile: Top 45%
Catalytic Cross-Coupling Reactions
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α-Arylation of Glutarimides via Ni/Ir Metallaphotoredox Cross-Electrophile Coupling — Dustin A. Bringley, Mareena C. Franke, et al. · The Journal of Organic Chemistry (2026) | TGRS Research Map | TGRS