Amine catalysis for the organocatalytic diboration of challenging alkenes

Farre, Albert; Soares, Kaline; Briggs, Rachel A.; Balanta, Angelica; Benoit, David M.; Bonet, Amadeu

Abstract

© 2016 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim The generation of in situ sp 2 –sp 3 diboron adducts has revolutionised the synthesis of organoboranes. Organocatalytic diboration reactions have represented a milestone in terms of unpredictable reactivity of these adducts. However, current methodologies have limitations in terms of substrate scope, selectivity and functional group tolerance. Here a new methodology based on the use of simple amines as catalyst is reported. This methodology provides a completely selective transformation overcoming current substrate scope and functional/protecting group limitations. Mechanistic studies have been included in this report.

Citation

Farre, A., Soares, K., Briggs, R. A., Balanta, A., Benoit, D. M., & Bonet, A. (2016). Amine catalysis for the organocatalytic diboration of challenging alkenes. Chemistry: a European journal, 22(49), 17552-17556. https://doi.org/10.1002/chem.201603979

• Journal Article Type: Article
• Acceptance Date: Sep 28, 2016
• Online Publication Date: Oct 26, 2016
• Publication Date: Dec 5, 2016
• Deposit Date: Sep 30, 2016
• Publicly Available Date: Oct 26, 2016
• Journal: Chemistry: a European journal
• Print ISSN: 0947-6539
• Publisher: Wiley
• Peer Reviewed: Peer Reviewed
• Volume: 22
• Issue: 49
• Pages: 17552-17556
• DOI: https://doi.org/10.1002/chem.201603979
• Keywords: Organoboron, Organocatalysis, Lewis base, Amines, Density functional calculations
• Public URL: https://hull-repository.worktribe.com/output/443716
• Publisher URL: http://onlinelibrary.wiley.com/doi/10.1002/chem.201603979/full
• Additional Information: Authors' accepted manuscript of article published in: Chemistry: a European journal, 2016, v.22, issue 49.
• Contract Date: Sep 30, 2016