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Pd-catalyzed Suzuki–Miyaura reactions of aryl halides using bulky biarylmonophosphine ligands

Nature Protocols volume 2, pages 31153121 (2007) | Download Citation

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Abstract

The following protocol describes the application of a highly active Pd-based catalyst system in the Suzuki–Miyaura cross-coupling reaction of arylboronic acids with aryl chlorides to provide biaryl compounds. The general procedure includes a detailed description of an appropriate reaction setup, two methods for assaying the crude reaction mixture (GC and TLC) and a procedure for the isolation, purification and characterization of the anticipated product. Reagents and catalyst precursors can be manipulated in the air; however, the cross-coupling reactions must be performed in an inert atmosphere. Two Suzuki–Miyaura reactions are included in the text as representative examples of these procedures. Although the reactions can proceed in less than 5 min, the protocols, including workup, generally take 6–30 h to be completed.

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Acknowledgements

Funds for this work were provided by the National Institutes of Health (GM 46059). We also acknowledge Merck, Amgen and Boehringer Ingelheim for additional unrestricted fiscal support. We thank BASF for a gift of Pd(OAc)2. R.A.A. thanks Pfizer for a graduate fellowship.

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  1. Department of Chemistry, Massachusetts Institute of Technology, 77 Massachusetts Avenue, 18-490, Cambridge, Massachusetts 02139, USA.

    • Ryan A Altman
    •  & Stephen L Buchwald

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Correspondence to Stephen L Buchwald.

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https://doi.org/10.1038/nprot.2007.411

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