Skip to main page content
U.S. flag

An official website of the United States government

Dot gov

The .gov means it’s official.
Federal government websites often end in .gov or .mil. Before sharing sensitive information, make sure you’re on a federal government site.

Https

The site is secure.
The https:// ensures that you are connecting to the official website and that any information you provide is encrypted and transmitted securely.

Access keys NCBI Homepage MyNCBI Homepage Main Content Main Navigation
. 2013 Jul 24;135(29):10642-5.
doi: 10.1021/ja405950c. Epub 2013 Jul 12.

Ligand-controlled palladium-catalyzed regiodivergent Suzuki-Miyaura cross-coupling of allylboronates and aryl halides

Yang Yang  1 , Stephen L Buchwald
Affiliations

Ligand-controlled palladium-catalyzed regiodivergent Suzuki-Miyaura cross-coupling of allylboronates and aryl halides

Yang Yang et al. J Am Chem Soc. .

Abstract

An orthogonal set of catalyst systems has been developed for the Suzuki-Miyaura coupling of 3,3-disubstituted and 3-monosubstituted allylboronates with (hetero)aryl halides. These methods allow for the highly selective preparation of either the α- or the γ-isomeric coupling product.

PubMed Disclaimer

Figures

Scheme 1
Scheme 1
Prenylated Natural Products and Proposed Regioselective Allylation of Aryl Halides.
Scheme 2
Scheme 2
Proposed Mechanism.
See this image and copyright information in PMC

References

    1. For recent reviews, see: Williams RM, Stocking EM, Sanz-Cervera JF. Top. Curr. Chem. 2000;209:97–173. Li S. Nat. Prod. Rep. 2010;27:57–78.

    1. For a recent review on prenylation methods, see: Lindel T, Marsch N, Adla SK. Top. Curr. Chem. 2012;309:67–130.

    1. For reviews, see: Hall DG, editor. Boronic Acids. Wiley-VCH; Weinheim, Germany: 2005. de Meijere A, Diederich F, editors. Metal-Catalyzed Cross-Coupling Reactions. 2nd ed Wiley-VCH; Weinheim, Germany: 2004.

    1. For selected reviews on the η3–η1–η3 interconversion of allylpalladium intermediate, see: Trost BM, Van Vranken DL. Chem. Rev. 1996;96:395–422. Pregosin PS, Salzmann R. Coord. Chem. Rev. 1996;155:35–68.

    1. For a recent study on the Suzuki-Miyaura coupling of allylboronates where regioselectivity was dictated by the substitution pattern of substrates, see: Glasspoole BW, Ghozati K, Moir JM, Crudden CM. Chem. Commun. 2012;48:1230–1232.

Publication types