Rhodium(I)-catalyzed carboxylation of aryl- and alkenylboronic esters with CO2.
When the esters of arylboronic acids with 2,2-dimethylpropan-1,3-diol were treated with a catalytic amount of [Rh(OH)(cod)]2 in the presence of 1,3-bis(diphenylphosphino)propane and CsF in dioxane at 60 degrees C under carbon dioxide atmosphere, the benzoic acid derivatives were obtained in good yields. Reactions of alkenylboronic esters also proceeded under similar conditions to give alpha,beta-unsaturated carboxylic acids. As these boronic esters are now easily available through coupling or direct borylation reactions, this method would be a useful method for the preparation of various functionalized aryl- and alkenyl-carboxylic acids.
Ukai
Kazutoshi
K
Department of Chemistry, Tokyo Institute of Technology, O-Okayama, Meguro-ku, Tokyo 152-8551, Japan.
Aoki
Masao
M
Takaya
Jun
J
Iwasawa
Nobuharu
N
D001897:Boronic Acids / Q000737:chemistry*; D002245:Carbon Dioxide / Q000737:chemistry*; D002264:Carboxylic Acids / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D004952:Esters / Q000737:chemistry*; D008024:Ligands; D015394:Molecular Structure; D012238:Rhodium / Q000737:chemistry*; D013237:Stereoisomerism
D001897:Boronic Acids; D002264:Carboxylic Acids; D004952:Esters; D008024:Ligands; D002245:Carbon Dioxide; D012238:Rhodium