%0 Journal Article
%@ 1523-7060
%A Kawamoto, T
%A Okada, T
%A Curran, DP
%A Ryu, I
%D 2013
%F pittir:20676
%J Organic Letters
%N 9
%P 2144 - 2147
%T Efficient hydroxymethylation reactions of iodoarenes using CO and 1,3-dimethylimidazol-2-ylidene borane
%U http://d-scholarship-dev.library.pitt.edu/20676/
%V 15
%X A hydroxymethylation reaction of a variety of iodoarenes proceeded effectively in the presence of CO, NHC-borane, diMeImd-BH3 (2) as a radical mediator, and a catalytic amount of AIBN. The reaction took place chemoselectively at the aryl-iodine bond but not at the aryl-bromine and aryl-chlorine bonds. A three-component coupling reaction comprising aryl iodides, CO, and electron-deficient alkenes also proceeded well to give unsymmetrical ketones in good yields. Control experiments show that 2 would act as a hydrogen donor to acyl radicals and iodinated NHC-borane as a reducing agent of aldehydes. © 2013 American Chemical Society.