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

Bang Li, Qi Mao, Jia Zhou, Feng Liu, Na Ye

Research output: Contribution to journalArticle

3 Citations (Scopus)

Abstract

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-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.

Original languageEnglish (US)
Pages (from-to)2242-2246
Number of pages5
JournalOrganic and Biomolecular Chemistry
Volume17
Issue number8
DOIs
StatePublished - Jan 1 2019

Fingerprint

Aniline Compounds
Maleimides
Michael reaction
aniline
Succinimides
Chemical activation
succinimides
activation
Electrons
Nucleophiles
nucleophiles
Alkenes
alkenes
reagents
electrons
selectivity
Metals
catalysts
Catalysts
Substrates

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

Cite this

HFIP-promoted Michael reactions : direct para-selective C-H activation of anilines with maleimides. / Li, Bang; Mao, Qi; Zhou, Jia; Liu, Feng; Ye, Na.

In: Organic and Biomolecular Chemistry, Vol. 17, No. 8, 01.01.2019, p. 2242-2246.

Research output: Contribution to journalArticle

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