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
. 2023 Aug 21;62(34):e202307973.
doi: 10.1002/anie.202307973. Epub 2023 Jul 13.

Cooperative Bimetallic Catalysis via One-Metal/Two-Ligands: Mechanistic Insights of Polyfluoroarylation-Allylation of Diazo Compounds

Gao-Yin Wang  1   2 , Zhaoliang Ge  2 , Kuiling Ding  1   2   3 , Xiaoming Wang  2   4
Affiliations

Cooperative Bimetallic Catalysis via One-Metal/Two-Ligands: Mechanistic Insights of Polyfluoroarylation-Allylation of Diazo Compounds

Gao-Yin Wang et al. Angew Chem Int Ed Engl. .

Abstract

Metal/ligand in situ assembly is crucial for tailoring the reactivity & selectivity in transition metal catalysis. Cooperative catalysis via a single metal/two ligands is still underdeveloped, since it is rather challenging to harness the distinct reactivity profiles of the species generated by self-assembly of a single metal precursor with a mixture of different ligands. Herein, we report a catalytic system composed of a single metal/two ligands for a three-component reaction of polyfluoroarene, α-diazo ester, and allylic electrophile, leading to highly efficient construction of densely functionalized quaternary carbon centers, that are otherwise hardly accessible. Mechanistic studies suggest this reaction follows a cooperative bimetallic pathway via two catalysts with distinct reactivity profiles, which are assembled in situ from a single metal precursor and two ligands and work in concert to escort the transformation.

Keywords: Cooperative Bimetallic Catalysis; Diazo Compounds; Difunctionalization; Metal/Ligand Assembly; One-Metal/Two-Ligands.

PubMed Disclaimer

References

    1. E. Ruijter, R. Scheffelaar, R. V. Orru, Angew. Chem. Int. Ed. 2011, 50, 6234-6246.
    1. S. C. Graebin, V. F. Ribeiro, R. K. Rogério, E. A. Kümmerle, Curr. Org. Synth. 2019, 16, 855-899.
    1. S. E. John, S. Gulati, N. Shankaraiah, Org. Chem. Front. 2021, 8, 4237-4287.
    1. M. P. Doyle, M. A. McKervey, T. Ye, Modern Catalytic Methods for Organic Synthesis with Diazo Compounds, Wiley-Interscience, New York, 1998.
    1. H. M. Davies, J. R. Manning, Nature 2008, 451, 417-424.

LinkOut - more resources