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Nickel-Catalyzed Domino Reaction of α-Aryloxyacetonitriles with Arylboronic Acids: Synthesis of 2-Aroylbenzo[ b ]furans.

Subhashini V SubramaniamVijaya Kumaran DharmalingamAnwesha BhattacharyaSaravanan Peruncheralathan
Published in: Organic letters (2023)
We disclose the first catalytic domino reaction of α-(2-formylaryloxy)acetonitriles with arylboronic acids, yielding a range of 2-aroylbenzo[ b ]furans with yields of up to 93%. Ni(acac) 2 serves as an effective dual catalyst. The protocol is also applicable to α-(2-acetylphenoxy)acetonitrile, giving rise to 3-methyl-2-aroylbenzo[ b ]furans. This domino process is efficient, additive-free, and compatible with a variety of aryl boronic acids, including those with CF 3 , NO 2 , CN, and CO 2 Me groups. Mechanistic studies highlight the dual activation facilitated by the nickel catalyst.
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