Palladium-Catalyzed Regioselective B(3,4)–H Acyloxylation of <i>o</i>-Carboranes
Yatong Fu, Li Yu, Donghong Luo, Yibo Lu, Jiajun Huang, Ziyi Yang, Jian Lu, Jian Lu, Yuan‐Ye Jiang, Ju‐You Lu, Ju‐You Lu
Abstract
We disclose herein an efficient regioselective B(3,4)–H activation via a ligand strategy, affording B(3)-monoacyloxylated and B(3,4)-diacyloxylated o-carboranes. The identification of amino acid and phosphoric acid ligands is crucial for the success of B(3)-mono- and B(3,4)-diacyloxylation, respectively. This ligand approach is compatible with a broad range of carboxylic acids. The functionalization of complex drug molecules is demonstrated. Other acyloxyl sources, including sodium benzoate, benzoic anhydride, and iodobenzene diacetate, are also tolerated.
Topics & Concepts
ChemistryRegioselectivityLigand (biochemistry)IodobenzenePalladiumBenzoic acidCatalysisPhosphoric acidStereochemistryMedicinal chemistryCombinatorial chemistryOrganic chemistryReceptorBiochemistryBoron Compounds in ChemistryRadiopharmaceutical Chemistry and ApplicationsPharmacological Effects and Toxicity Studies