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Photoinduced Copper-Catalyzed C(sp3)-P Bond Formation by Coupling of Secondary Phosphines with N-(Acyloxy)phthalimides and N-Fluorocarboxamides.

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A photoinduced copper-catalyzed C(sp3)-P bond formation has been developed by using N-(acyloxy)phthalimides as radical precursors and secondary phosphine boranes as coupling partners. A variety of alkyl carboxylic acid derivatives can… Click to show full abstract

A photoinduced copper-catalyzed C(sp3)-P bond formation has been developed by using N-(acyloxy)phthalimides as radical precursors and secondary phosphine boranes as coupling partners. A variety of alkyl carboxylic acid derivatives can be readily transformed into the corresponding phosphines with high reaction efficiency and structural diversity. Besides, utilizing the 1,5-HAT of the N-centered radical process, the δ C(sp3)-H bond can be coupled with secondary phosphines, which provides a novel method for the regioselective formation of C(sp3)-P bonds.

Keywords: sp3 bond; formation; copper catalyzed; photoinduced copper; catalyzed sp3; bond

Journal Title: Organic letters
Year Published: 2023

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