title: Free radical-mediated hydroxymethylation using CO and HCHO.
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.
authors.forename: Takuji
authors.initials: T
authors.lastname: Kawamoto
authors.forename: Ilhyong
authors.initials: I
authors.lastname: Ryu
mesh_terms: D001894:Borohydrides / Q000737:chemistry*; D002248:Carbon Monoxide / Q000737:chemistry*; D005557:Formaldehyde / Q000737:chemistry*; D005609:Free Radicals / Q000737:chemistry*; D006846:Hydrocarbons, Halogenated / Q000737:chemistry*; D008745:Methylation; D015394:Molecular Structure
chemical_list: D001894:Borohydrides; D005609:Free Radicals; D006846:Hydrocarbons, Halogenated; D005557:Formaldehyde; D002248:Carbon Monoxide