4.6 Article

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

Journal

ORGANIC & BIOMOLECULAR CHEMISTRY
Volume 17, Issue 8, Pages 2242-2246

Publisher

ROYAL SOC CHEMISTRY
DOI: 10.1039/c8ob03073a

Keywords

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Funding

  1. National Natural Science Foundation of China [81703330]
  2. Natural Science Foundation of Jiangsu Province [BK20170347]
  3. Jiangsu Key Laboratory of Neuropsychiatric Diseases [BM2013003]

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The Michael reaction is widely used for the C-C coupling of electron-poor olefins and C(sp(3))-H pronucleophiles. Herein, an effective Michael reaction approach between electron-rich aromatic and heteroaromatic substrates as C(sp(2))-H nucleophiles with maleimides as electrophiles in 1,1,1,3,3,3-hexafluoro2- 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.

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