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Issue 12, 2018
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Selective formation of phthalimides from amines, aldehydes and CO by Pd-catalyzed oxidative C–H aminocarbonylation

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Abstract

Pd-Catalyzed C–H bond aminocarbonylation represents one of the most significant approaches to the synthesis of amides. It still remains a challenge due to the decomposition of catalysts and poor chemoselectivity. To overcome the above difficulties, imines are used as the amine source to achieve aminocarbonylation. The in situ generated imines could also act as a directing group to induce C–H bond activation. This transformation provides an efficient and straightforward protocol for the synthesis of phthalimide derivatives which widely exist in natural products, pharmaceuticals and functional materials from amines, aldehydes and CO in one pot. Various functional groups are tolerated and the yields are up to 99%.

Graphical abstract: Selective formation of phthalimides from amines, aldehydes and CO by Pd-catalyzed oxidative C–H aminocarbonylation

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Publication details

The article was received on 15 Mar 2018, accepted on 23 Apr 2018 and first published on 01 May 2018


Article type: Research Article
DOI: 10.1039/C8QO00282G
Citation: Org. Chem. Front., 2018,5, 1957-1961
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    Selective formation of phthalimides from amines, aldehydes and CO by Pd-catalyzed oxidative C–H aminocarbonylation

    R. Shi, F. Liao, H. Niu and A. Lei, Org. Chem. Front., 2018, 5, 1957
    DOI: 10.1039/C8QO00282G

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