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  • Title: Decarboxylative Cross-Coupling Enabled by Fe and Ni Metallaphotoredox Catalysis.
    Author: Nsouli R, Nayak S, Balakrishnan V, Lin JY, Chi BK, Ford HG, Tran AV, Guzei IA, Bacsa J, Armada NR, Zenov F, Weix DJ, Ackerman-Biegasiewicz LKG.
    Journal: J Am Chem Soc; 2024 Oct 30; 146(43):29551-29559. PubMed ID: 39422549.
    Abstract:
    Decarboxylative cross-coupling of carboxylic acids and aryl halides has become a key transformation in organic synthesis to form C(sp2)-C(sp3) bonds. In this report, a base metal pairing between Fe and Ni has been developed with complementary reactivity to the well-established Ir and Ni metallaphotoredox reactions. Utilizing an inexpensive FeCl3 cocatalyst along with a pyridine carboxamidine Ni catalyst, a range of aryl iodides can be preferentially coupled to carboxylic acids over boronic acid esters, triflates, chlorides, and even bromides in high yields. Additionally, carboxylic acid derivatives containing heterocycles, N-protected amino acids, and protic functionality can be coupled in 23-96% yield with a range of sterically hindered, electron-rich, and electron-deficient aryl iodides. Preliminary catalytic and stoichiometric reactions support a mechanism in which Fe is responsible for the activation of carboxylic acid upon irradiation with light and a NiI alkyl intermediate is responsible for activation of the aryl iodide coupling partner followed by reductive elimination to generate product.
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