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

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‐carbor...

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Bibliographic Details
Published in:ChemCatChem 2022-04, Vol.14 (8), p.n/a
Main Authors: Yang, Ziyi, Sun, Chaofan, Wei, Xing, Lu, Jian, Lu, Ju‐You
Format: Article
Language:English
Subjects:
B−H functionalization
Carborane
Coupling
nido-carboranes
Palladium
palladium catalysis
Phosphines
Regioselectivity
step-economy
Substrates
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Summary: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. Carborane chemistry: 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 of nido‐carboranes. 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.
ISSN:1867-3880
1867-3899
DOI:10.1002/cctc.202101571