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Ligand-enabled ortho-C–H olefination of phenylacetic amides with unactivated alkenes

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Abstract

Although chelation-assisted C–H olefination has been intensely investigated, Pd(II)-catalyzed C–H olefination reactions are largely restricted to acrylates and styrenes. Here we report a quinoline-derived ligand that enables the Pd(II)-catalyzed olefination of the C(sp2)–H bond with simple aliphatic alkenes using a weakly coordinating monodentate amide auxiliary. Oxygen is used as the terminal oxidant with catalytic copper as the co-oxidant. A variety of functional groups in the aliphatic alkenes are tolerated. Upon hydrogenation, the ortho-alkylated product can be accessed. The utility of this reaction is also demonstrated by the late-stage diversification of drug molecules.

Graphical abstract: Ligand-enabled ortho-C–H olefination of phenylacetic amides with unactivated alkenes

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Publication details

The article was received on 08 Nov 2017, accepted on 08 Dec 2017 and first published on 08 Dec 2017


Article type: Edge Article
DOI: 10.1039/C7SC04827K
Citation: Chem. Sci., 2018, Advance Article
  • Open access: Creative Commons BY-NC license
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    Ligand-enabled ortho-C–H olefination of phenylacetic amides with unactivated alkenes

    M. Lu, X. Chen, H. Xu, H. Dai and J. Yu, Chem. Sci., 2018, Advance Article , DOI: 10.1039/C7SC04827K

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