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. 2011:7:808-12.
doi: 10.3762/bjoc.7.92. Epub 2011 Jun 15.

Au(I)/Au(III)-catalyzed Sonogashira-type reactions of functionalized terminal alkynes with arylboronic acids under mild conditions

Deyun Qian  1 , Junliang Zhang
Affiliations

Au(I)/Au(III)-catalyzed Sonogashira-type reactions of functionalized terminal alkynes with arylboronic acids under mild conditions

Deyun Qian et al. Beilstein J Org Chem. 2011.

Abstract

A straightforward, efficient, and reliable redox catalyst system for the Au(I)/Au(III)-catalyzed Sonogashira cross-coupling reaction of functionalized terminal alkynes with arylboronic acids under mild conditions has been developed.

Keywords: Sonogashira cross-coupling; arylboronic acid; gold-catalysis.

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Figures

Scheme 1
Scheme 1
Previous work and our projected gold-catalyzed Sonogashira-type cross-coupling.
Scheme 2
Scheme 2
Scope of the Sonogashira-type cross-coupling reaction (isolated yield). aAgOTf in place of AgBF4. bYield determined by 1H NMR, the prouduct could not be separated from the unreacted starting material. cAgOTf in place of AgBF4, RT, 36 h.
Scheme 3
Scheme 3
Proposed mechanism for the Au(I)/Au(III)-catalyzed Sonogashira-type cross-coupling.
See this image and copyright information in PMC

References

    1. Chinchilla R, Nájera C. Chem Rev. 2007;107:874–922. doi: 10.1021/cr050992x. - DOI - PubMed
    1. Doucet H, Hierso J-C. Angew Chem, Int Ed. 2007;46:834–871. doi: 10.1002/anie.200602761. - DOI - PubMed
    1. Plenio H. Angew Chem, Int Ed. 2008;47:6954–6956. doi: 10.1002/anie.200802270. - DOI - PubMed
    1. Tougerti A, Negri S, Jutand A. Chem–Eur J. 2007;13:666–676. doi: 10.1002/chem.200600574. - DOI - PubMed
    1. Ahlquist M, Norrby P-O. Organometallics. 2007;26:550–553. doi: 10.1021/om0604932. - DOI

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