Radical addition of alkyl halides to formaldehyde in the presence of cyanoborohydride as a radical mediator. A new protocol for hydroxymethylation reaction

Takuji Kawamoto, Takahide Fukuyama, Ilhyong Ryu*

*Corresponding author for this work

Research output: Contribution to journalArticle

47 Scopus citations

Abstract

Hydroxymethylation of alkyl halides was achieved using paraformaldehyde as a radical C1 synthon in the presence of tetrabutylammonium cyanoborohydride as a hydrogen source. The reaction proceeds via a radical chain mechanism involving an alkyl radical addition to formaldehyde to form an alkoxy radical, which abstracts hydrogen from a hydroborate anion.

Original languageEnglish
Pages (from-to)875-877
Number of pages3
JournalJournal of the American Chemical Society
Volume134
Issue number2
DOIs
StatePublished - 18 Jan 2012

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