Stoichiometric and catalytic C-C and C-H bond formation with B(C6F5)3 via cationic intermediates

Soltani, Yashar, Wilkins, Lewis C. and Melen, Rebecca L. ORCID: https://orcid.org/0000-0003-3142-2831 2017. Stoichiometric and catalytic C-C and C-H bond formation with B(C6F5)3 via cationic intermediates. Angewandte Chemie International Edition 56 (39) , pp. 11995-11999. 10.1002/anie.201704789

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Abstract

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(C6F5)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(C6F5)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.

Item Type:	Article
Date Type:	Publication
Status:	Published
Schools:	Chemistry
Publisher:	Wiley
ISSN:	1433-7851
Date of First Compliant Deposit:	18 July 2017
Date of Acceptance:	12 July 2017
Last Modified:	07 Nov 2023 06:00
URI:	https://orca.cardiff.ac.uk/id/eprint/102559

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