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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

Contributor(s):
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
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Publication History

Publication Date:
17 September 2019 (online)

 
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Key words

gold catalysis - nanoparticles - Stille coupling - benzyl halides - allylstannanes - dienes

Significance

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).


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Comment

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.


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