Synfacts 2019; 15(10): 1163
DOI: 10.1055/s-0039-1690959
Polymer-Supported Synthesis
© Georg Thieme Verlag Stuttgart · New York

Stille Coupling Catalyzed by Gold Nanoparticles Formed In Situ on Active Carbon

Yasuhiro Uozumi
Shun Ichii
Holz J, Pfeffer C, Zuo H, Beierlein D, Richter G, Klemm E, Peters R. * Universität Stuttgart and MPI IS Stuttgart, Germany
In Situ Generated Gold Nanoparticles on Active Carbon as Reusable Highly Efficient Catalysts for a C(sp3)–C(sp3) Stille Coupling.

Angew. Chem. Int. Ed. 2019;
58: 10330-10334
Further Information

Publication History

Publication Date:
17 September 2019 (online)



Activated-carbon-adsorbed gold nanoparticles formed in situ catalyzed the C(sp3)–C(sp3) coupling reaction of benzylic bromides with allyl(tributyl)stannanes to give the corresponding homoallylic benzenes in up to >99% yield (eq.1). This catalyst was also applicable on an allyl–allyl coupling reaction to furnish 1,5-dienes in yields of 54–59% (eq. 2).



The coupling of (2-bromoethyl)benzene with allyl(tributyl)stannane proceeded in the presence of a 0.001 mol% loading of the gold nanoparticles to give the coupling product in 29% yield with a total turnover number of up to 29000. The catalyst was recovered by centrifugation and recycled four times without a loss of its catalytic activity.