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Palladium‐Catalyzed Cascade Deboronation/Regioselective B−P Coupling of <i>closo</i>‐Carboranes

Ziyi Yang, Chaofan Sun, Xing Wei, Jian Lu, Ju‐You Lu

2022ChemCatChem10 citationsDOI

Abstract

Abstract A cascade deboronation/regioselective B−P coupling of closo ‐carboranes is disclosed using a combination of palladium catalysts and nitrogen or phosphine‐containing directing groups. Unsymmetric C‐substituted closo ‐carboranes, including C‐monosubstituted and unsymmetric 1,2‐disubstituted closo ‐carboranes, are tolerated. Select closo ‐carboranes bearing other directing groups, such as benzoxazole, and diphenylphosphine, are compatible substrates for this reaction. Phosphine and arsenic can be utilized as effective coupling partners. Furthermore, a catalytic amount of palladium salt mediates the regioselective B−H activation process. Readily available closo ‐carboranes as the starting materials for direct one‐pot synthesis of functionalized nido ‐carboranes and the in‐situ formation of nido ‐carborane intermediates without purification are important features in terms of practical applications.

Topics & Concepts

RegioselectivityChemistryPalladiumPhosphineCatalysisCarboraneCombinatorial chemistryDiphenylphosphineBoranesMedicinal chemistryOrganic chemistryBoronBoron Compounds in ChemistryRadiopharmaceutical Chemistry and ApplicationsOrganoboron and organosilicon chemistry
Palladium‐Catalyzed Cascade Deboronation/Regioselective B−P Coupling of <i>closo</i>‐Carboranes | Litcius