Synthesis of Highly Functionalized Bismacycles via Post-Transmetallation Modification of Arylboronic Acids

Sivanandan, Sudheesh T.; Owen, Benjamin; Guiry, Patrick J.; Ball, Liam T.

Abstract

Bismacycles featuring a sulfone-bridged scaffold have recently been developed as versatile and convenient electrophilic arylating agents. Here, we report that the exocyclic aryl group, which is ultimately transferred to a nucleophilic coupling partner, can be functionalized through cross-coupling, heteroatom substitutions, oxidations and reductions, and protecting group manipulations. This “postsynthetic modification” approach provides concise and divergent access to complex aryl bismacycles. The utility of the functionalized bismacycles in electrophilic arylation of C–H and O–H bonds is demonstrated.

Citation

Sivanandan, S. T., Owen, B., Guiry, P. J., & Ball, L. T. (2023). Synthesis of Highly Functionalized Bismacycles via Post-Transmetallation Modification of Arylboronic Acids. Journal of Organic Chemistry, 88(14), 9730–9736. https://doi.org/10.1021/acs.joc.3c00361

• Journal Article Type: Article
• Acceptance Date: Jun 29, 2023
• Online Publication Date: Jul 12, 2023
• Publication Date: Jul 21, 2023
• Deposit Date: Jul 31, 2023
• Publicly Available Date: Aug 1, 2023
• Journal: Journal of Organic Chemistry
• Print ISSN: 0022-3263
• Electronic ISSN: 1520-6904
• Publisher: American Chemical Society
• Peer Reviewed: Peer Reviewed
• Volume: 88
• Issue: 14
• Pages: 9730–9736
• DOI: https://doi.org/10.1021/acs.joc.3c00361
• Keywords: Arylation, Cross coupling reaction, Functionalization, Oxidation, Reagents
• Public URL: https://nottingham-repository.worktribe.com/output/23005502
• Publisher URL: https://pubs.acs.org/doi/10.1021/acs.joc.3c00361