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Issue 8, 2019
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HFIP-promoted Michael reactions: direct para-selective C–H activation of anilines with maleimides

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Abstract

The Michael reaction is widely used for the C–C coupling of electron-poor olefins and C(sp3)–H pronucleophiles. Herein, an effective Michael reaction approach between electron-rich aromatic and heteroaromatic substrates as C(sp2)–H nucleophiles with maleimides as electrophiles in 1,1,1,3,3,3-hexafluoro-2-propanol (HFIP) was first presented without the need for any additional metal catalysts or reagents. This reaction provides a concise and environmentally friendly strategy for the facile construction of 3-aryl succinimides from N,N-disubstituted anilines and maleimides with high para selectivity.

Graphical abstract: HFIP-promoted Michael reactions: direct para-selective C–H activation of anilines with maleimides

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Publication details

The article was received on 11 Dec 2018, accepted on 28 Jan 2019 and first published on 28 Jan 2019


Article type: Paper
DOI: 10.1039/C8OB03073A
Citation: Org. Biomol. Chem., 2019,17, 2242-2246

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    HFIP-promoted Michael reactions: direct para-selective C–H activation of anilines with maleimides

    B. Li, Q. Mao, J. Zhou, F. Liu and N. Ye, Org. Biomol. Chem., 2019, 17, 2242
    DOI: 10.1039/C8OB03073A

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