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Visible light-mediated gold-catalysed carbon(sp2)-carbon(sp) cross-coupling
Suhong Kim1, Jaime Rojas-Martin1,2, F Dean Toste1
1Department of Chemistry , University of California , Berkeley , CA 94720 , USA .
Chemical Science
|June 5, 2018
Summary
This study introduces a novel dual catalytic reaction combining photoredox and gold catalysis for cross-coupling alkynes and diazonium salts. The method efficiently synthesizes aryl-alkynyl compounds, showing high selectivity for silyl-substituted alkynes.
Area of Science:
- Organic Chemistry
- Catalysis
- Synthetic Methodology
Background:
- Cross-coupling reactions are fundamental in organic synthesis.
- Developing new catalytic systems for C-C bond formation is crucial.
- Alkynylsilanes offer unique reactivity in coupling reactions.
Purpose of the Study:
- To develop a novel dual photoredox and gold-catalysed cross-coupling reaction.
- To couple alkynyltrimethylsilanes with aryldiazonium salts.
- To investigate the reaction mechanism and selectivity.
Main Methods:
- Visible-light photoredox catalysis.
- Gold catalysis.
- Cross-coupling of alkynyltrimethylsilanes and aryldiazonium tetrafluoroborates.
Main Results:
- A dual catalytic system was successfully established.
- The reaction proceeds via oxidative addition, transmetalation, and reductive elimination.
- Exclusive selectivity for silyl-substituted alkynes was achieved.
- Terminal alkynes showed no reactivity.
Conclusions:
- The developed dual catalytic system provides an efficient route to aryl-alkynyl compounds.
- The reaction mechanism involves synergistic action of photoredox and gold catalysts.
- The observed selectivity highlights the utility of silyl-protected alkynes in this transformation.
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