Free radical-mediated hydroxymethylation using CO and HCHO

Takuji Kawamoto, Ilhyong Ryu*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

11 Scopus citations

Abstract

Tin-free radical hydroxymethylations of haloalkanes using CO and HCHO as a C1 unit proceed efficiently in the presence of borohydrides as radical mediators. In the approach using CO, the formation of aldehydes by radical carbonylation and their subsequent reduction by hydrides lead to alcohols. On the other hand, the use of formaldehyde is more straightforward, in which the key reaction is alkyl radical addition to formaldehyde to give alkoxy radical, which abstracts hydrogen from borohydride reagents. The cascade sequences were observed in the reaction of cholesteryl bromide with HCHO, which displays the diverse applications of HCHO in radical chemistry.

Original languageEnglish
Pages (from-to)372-376
Number of pages5
JournalChimia
Volume66
Issue number6
DOIs
StatePublished - 1 Jun 2012

Keywords

  • Borohydrides
  • Carbon monoxide
  • Formaldehyde
  • Hydroxymethylation
  • One-carbon homologation
  • Radical reaction

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