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Oxidative Heck Coupling Using Pd(II) Supported on Organosilane-Functionalized Silica Mesocellular Foam

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Abstract

Oxidative Heck couplings of arylboronic acids and olefins are carried out under air to facilitate reoxidation of palladium without the need for an added co-oxidant using Pd(II) supported on silica surface-tethered bipyridyl, iminopyridine, or 3-aminopropyl ligands. Use of silica-supported iminopyridine or bipyridine ligands gives active catalysts, with the bipyridine-based catalyst being most efficient. The Heck products are formed with high yields and selectivities over the 1,4-addition product, and the silica supported bipyridine-based catalyst is easily recovered via simple filtration. Unlike similar supported catalysts in traditional Heck reactions involving aryl halides and olefins, the catalysts presented here can be used for multiple catalytic cycles without activity or selectivity loss.

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Acknowledgments

The authors would like to acknowledge partial financial support for this research from the US Department of Energy office of Basic Energy Sciences through Catalysis Science contract DE-FG02-03ER15459.

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Authors and Affiliations

  1. School of Chemical & Biomolecular Engineering, Georgia Institute of Technology, 311 Ferst Drive NW, Atlanta, GA, 30332, USA

    Eric W. Ping, Krishnan Venkatasubbaiah, Thomas F. Fuller & Christopher W. Jones

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  1. Eric W. Ping
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  2. Krishnan Venkatasubbaiah
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  3. Thomas F. Fuller
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  4. Christopher W. Jones
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Correspondence to Christopher W. Jones.

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Ping, E.W., Venkatasubbaiah, K., Fuller, T.F. et al. Oxidative Heck Coupling Using Pd(II) Supported on Organosilane-Functionalized Silica Mesocellular Foam. Top Catal 53, 1048–1054 (2010). https://doi.org/10.1007/s11244-010-9530-8

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  • DOI: https://doi.org/10.1007/s11244-010-9530-8

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