title: Radical addition of alkyl halides to formaldehyde in the presence of cyanoborohydride as a radical mediator. A new protocol for hydroxymethylation reaction.
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.
authors.affiliation: Department of Chemistry, Graduate School of Science, Osaka Prefecture University, Sakai, Osaka 599-8531, Japan.
authors.forename: Takuji
authors.initials: T
authors.lastname: Kawamoto
authors.forename: Takahide
authors.initials: T
authors.lastname: Fukuyama
authors.forename: Ilhyong
authors.initials: I
authors.lastname: Ryu