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. 2023 Oct 16;62(42):e202310493.
doi: 10.1002/anie.202310493. Epub 2023 Sep 7.

Gold-Catalyzed 1,2-Dicarbofunctionalization of Alkynes with Organohalides

Shashank P Sancheti  1 , Yukta Singh  1 , Manoj V Mane  2 , Nitin T Patil  1
Affiliations

Gold-Catalyzed 1,2-Dicarbofunctionalization of Alkynes with Organohalides

Shashank P Sancheti et al. Angew Chem Int Ed Engl. .

Abstract

Herein, we report the first gold-catalyzed 1,2-dicarbofunctionalization of alkynes using organohalides as non-prefunctionalized coupling partners. The mechanism of the reaction involves an oxidative addition/π-activation mechanism in contrast to the migratory insertion/cis-trans isomerization pathway that is predominantly observed with other transition metals yielding products with anti-selectivity. Mechanistic insights include several control experiments, NMR studies, HR-MSMS analyses, and DFT calculations that strongly support the proposed mechanism.

Keywords: Alkynes; DFT Studies; Dicarbofunctionalization; Gold; Redox Catalysis.

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References

    1. J. A. Ragan, Addition to Carbon-Carbon Multiple Bonds. Practical Synthetic Organic Chemistry (Ed.: S. Caron), Wiley, New York 2020, pp. 169-230.
    1. Selected reviews:
    1. Y. Shimizu, M. Kanai, Tetrahedron Lett. 2014, 55, 3727-3737;
    1. Z. J. Garlets, D. R. White, J. P. Wolfe, Asian J. Org. Chem. 2017, 6, 636-653;
    1. R. K. Dhungana, K. C. Shekhar, P. Basnet, R. Giri, Chem. Rec. 2018, 18, 1314-1340;

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