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Stoichiometric and Catalytic C−C and C−H Bond Formation with B(C 6 F 5 ) 3 via Cationic Intermediates
Author(s) -
Soltani Yashar,
Wilkins Lewis C.,
Melen Rebecca L.
Publication year - 2017
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201704789
Subject(s) - catalysis , chemistry , intramolecular force , isocoumarins , alkyne , cationic polymerization , borane , lewis acids and bases , medicinal chemistry , alkyl , carbon–carbon bond , stoichiometry , polymer chemistry , stereochemistry , organic chemistry
This work showcases a new catalytic cyclization reaction using a highly Lewis acidic borane with concomitant C−H or C−C bond formation. The activation of alkyne‐containing substrates with B(C 6 F 5 ) 3 enabled the first catalytic intramolecular cyclizations of carboxylic acid substrates using this Lewis acid. In addition, intramolecular cyclizations of esters enable C−C bond formation as catalytic B(C 6 F 5 ) 3 can be used to effect formal 1,5‐alkyl migrations from the ester functional groups to unsaturated carbon–carbon frameworks. This metal‐free method was used for the catalytic formation of complex dihydropyrones and isocoumarins in very good yields under relatively mild conditions with excellent atom efficiency.