Open AccessFree Radical-mediated Hydroxymethylation Using CO and HCHO
Author(s) -
Takuji Kawamoto,
Ilhyong Ryu
Publication year - 2012
Publication title -
chimia
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.387
H-Index - 55
eISSN - 2673-2424
pISSN - 0009-4293
DOI - 10.2533/chimia.2012.372
Subject(s) - chemistry , carbonylation , formaldehyde , reagent , radical , photochemistry , borohydride , alkyl , tin , bromide , organic chemistry , carbon monoxide , catalysis
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.