@article{pittir20676, volume = {15}, number = {9}, month = {May}, author = {T Kawamoto and T Okada and DP Curran and I Ryu}, title = {Efficient hydroxymethylation reactions of iodoarenes using CO and 1,3-dimethylimidazol-2-ylidene borane}, journal = {Organic Letters}, pages = {2144 -- 2147}, year = {2013}, url = {http://d-scholarship-dev.library.pitt.edu/20676/}, abstract = {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. {\copyright} 2013 American Chemical Society.} }