In Situ Generated Gold Nanoparticles on Active Carbon as Reusable Highly Efficient Catalysts for a Csp3 −Csp3 Stille Coupling

Gold nanoparticle catalysts are important in many industrial production processes. Nevertheless, for traditional Csp2 −Csp2 cross‐coupling reactions they have been rarely used and Pd catalysts usually give a superior performance. Herein we report that in situ formed gold metal nanoparticles are high...

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Veröffentlicht in:Angewandte Chemie International Edition 2019-07, Vol.58 (30), p.10330-10334
Hauptverfasser: Holz, Julia, Pfeffer, Camilla, Zuo, Hualiang, Beierlein, Dennis, Richter, Gunther, Klemm, Elias, Peters, René
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Sprache:eng
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Zusammenfassung:Gold nanoparticle catalysts are important in many industrial production processes. Nevertheless, for traditional Csp2 −Csp2 cross‐coupling reactions they have been rarely used and Pd catalysts usually give a superior performance. Herein we report that in situ formed gold metal nanoparticles are highly active catalysts for the cross coupling of allylstannanes and activated alkylbromides to form Csp3 −Csp3 bonds. Turnover numbers up to 29 000 could be achieved in the presence of active carbon as solid support, which allowed for convenient catalyst recovery and reuse. The present study is a rare case where a gold metal catalyst is superior to Pd catalysts in a cross‐coupling reaction of an organic halide and an organometallic reagent. Black gold: In situ formed Au metal nanoparticles are highly active catalysts for the cross coupling of allylstannanes and activated alkylbromides to form Csp3 −Csp3 bonds. Turnover numbers up to 29 000 could be achieved by using active carbon as solid support, which allowed convenient catalyst recovery and reuse. This is a rare case where a Au catalyst is superior to Pd catalysts in a cross‐coupling reaction of an organic halide and an organometallic reagent.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201902352