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Copper-Catalyzed Nitrogen Atom Transfer to Isoquinolines via C-N Triple Bond Cleavage and Three-Component Cyclization.

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A copper(I)-catalyzed tandem reaction of 2-bromoaryl ketones, terminal alkynes, and CH3CN is developed, which combines N atom transfer and three-component [3 + 2 + 1] cyclization, and efficiently produces densely… Click to show full abstract

A copper(I)-catalyzed tandem reaction of 2-bromoaryl ketones, terminal alkynes, and CH3CN is developed, which combines N atom transfer and three-component [3 + 2 + 1] cyclization, and efficiently produces densely functionalized isoquinolines in a facile, highly selective, and general manner. In the reaction, the formation of aromatic C-N bonds along with the complete C-N triple bond cleavage is first realized; Cu(III)-acetylide species might serve as the intermediates, which allow highly selective 6-endo-dig cyclization.

Keywords: atom transfer; three component; cyclization; component cyclization; copper catalyzed; triple bond

Journal Title: Organic letters
Year Published: 2022

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