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- W4384694448 abstract "Reactions that cleave C–C bonds and enable functionalization at both carbon sites are powerful strategic tools in synthetic chemistry. Stereodefined cyclopropyl ketones have become readily available and would be an ideal source of 3-carbon fragments, but general approaches to net C–C activation / difunctionalization are unknown. Herein we demonstrate the cross-coupling of cyclopropyl ketones with organozinc reagents and chlorotrimethylsilane to form 1,3-difunctionalized, ring-opened products. A combination of experimental and theoretical studies rule out more established mechanisms and shed light on how cooperation between the redox-active terpyridine (tpy) ligand and the nickel atom enables the C–C bond activation step. The reduced (tpy•–)NiI species activates the C–C bond via a concerted asynchronous ring-opening transition state. The resulting alkylnickel(II) intermediate can then be engaged by aryl-, alkenyl-, and alkylzinc reagents to furnish cross-coupled products. This allows quick access to products that are difficult to make by conjugate addition methods, such as β-allylated and β-benzylated enol ethers. The utility of this approach is demonstrated in the synthesis of a key (±)-taiwaniaquinol B intermediate and the total synthesis of prostaglandin D1." @default.
- W4384694448 created "2023-07-20" @default.
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- W4384694448 date "2023-07-18" @default.
- W4384694448 modified "2023-09-23" @default.
- W4384694448 title "Ligand-Metal Cooperation Enables Net C–C Activation Cross-Coupling Reactivity of Cyclopropyl Ketones" @default.
- W4384694448 doi "https://doi.org/10.26434/chemrxiv-2021-hjdbr-v3" @default.
- W4384694448 hasPublicationYear "2023" @default.
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