Radical Addition of Alkyl Halides to Formaldehyde in the Presence of Cyanoborohydride as a Radical Mediator. A New Protocol for Hydroxymethylation Reaction

T Kawamoto, T Fukuyama, I Ryu

文献索引：Kawamoto, Takuji; Fukuyama, Takahide; Ryu, Ilhyong Journal of the American Chemical Society, 2012 , vol. 134, # 2 p. 875 - 877

全文：HTML全文

被引用次数: 27

摘要

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.