Science· 2014Q1
Merging photoredox with nickel catalysis: Coupling of α-carboxyl sp <sup>3</sup> -carbons with aryl halides
- 1,588citations
- Q1SCImago
- 2014year
Short summary
A synergistic photoredox and nickel catalysis approach enables direct cross-coupling of α-carboxyl sp<sup>3</sup>-carbons with aryl halides, including amino acids and substituted carboxylic acids.
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Key points
- Developed a synergistic photoredox and nickel catalysis system for sp<sup>3</sup>-sp<sup>2</sup> cross-coupling.
- Achieved direct decarboxylative coupling of amino acids and substituted carboxylic acids with aryl halides.
- Demonstrated application to direct sp<sup>3</sup>-C(H) functionalization of dimethylaniline with aryl halides.
AI-generated from the title and abstract; the full text is not read.
Abstract
Over the past 40 years, transition metal catalysis has enabled bond formation between aryl and olefinic (sp(2)) carbons in a selective and predictable manner with high functional group tolerance. Couplings involving alkyl (sp(3)) carbons have proven more challenging. Here, we demonstrate that the synergistic combination of photoredox catalysis and nickel catalysis provides an alternative cross-coupling paradigm, in which simple and readily available organic molecules can be systematically used as coupling partners. By using this photoredox-metal catalysis approach, we have achieved a direct decarboxylative sp(3)-sp(2) cross-coupling of amino acids, as well as α-O- or phenyl-substituted carboxylic acids, with aryl halides. Moreover, this mode of catalysis can be applied to direct cross-coupling of C(sp³)-H in dimethylaniline with aryl halides via C-H functionalization.
The authors' abstract, as published at the source. Science, 2014 · DOI ↗
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Field: Organic Chemistry
Organic ChemistryChemistry