Radical-mediated intramolecular β-C(sp3)-H amidation of alkylimidates: Facile synthesis of 1,2-amino alcohols

Xue Qing Mou, Xiang Yu Chen, Gong Chen, Gang He

Research output: Contribution to journalArticle

24 Citations (Scopus)

Abstract

A new radical-mediated intramolecular β-C(sp3)-H amidation reaction of O-alkyl trichloro- or arylimidates is reported. Various oxazolines were efficiently prepared from easily accessible alcohol starting materials. The trichloro-oxazoline products can be hydrolyzed under mild conditions to give valuable 1,2-amino alcohols. This amidation reaction exhibits a broad substrate scope and good functional group tolerance, and offers a powerful means for the C(sp3)-H functionalization of alcohols. Mechanistic studies suggest that a sequence of 1,5-HAT of an imidate radical, iodination and cyclization might be operative.

Original languageEnglish (US)
Pages (from-to)515-518
Number of pages4
JournalChemical Communications
Volume54
Issue number5
DOIs
StatePublished - Jan 1 2018

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Amino alcohols
Amino Alcohols
Alcohols
Imidoesters
Cyclization
Functional groups
Substrates

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Electronic, Optical and Magnetic Materials
  • Ceramics and Composites
  • Chemistry(all)
  • Surfaces, Coatings and Films
  • Metals and Alloys
  • Materials Chemistry

Cite this

Mou, Xue Qing ; Chen, Xiang Yu ; Chen, Gong ; He, Gang. / Radical-mediated intramolecular β-C(sp3)-H amidation of alkylimidates : Facile synthesis of 1,2-amino alcohols. In: Chemical Communications. 2018 ; Vol. 54, No. 5. pp. 515-518.
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Radical-mediated intramolecular β-C(sp3)-H amidation of alkylimidates : Facile synthesis of 1,2-amino alcohols. / Mou, Xue Qing; Chen, Xiang Yu; Chen, Gong; He, Gang.

In: Chemical Communications, Vol. 54, No. 5, 01.01.2018, p. 515-518.

Research output: Contribution to journalArticle

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