Bismuth(V)-Mediated C–H Arylation of Phenols and Naphthols

Senior, Aaron; Ball, Liam T.

Abstract

We recently reported a general and practical strategy for the Bi(V)-mediated C–H arylation of phenols and naphthols. Our telescoped protocol proceeds via transmetallation from readily available arylboronic acids to a stable Bi(III) precursor, oxidation to a reactive Bi(V) intermediate, and subsequent ortho-selective phenol arylation. The process exhibits broad scope with respect to both components and tolerates functionality that is incompatible with conventional cross-coupling methods. Preliminary investigations provide insight into the mechanism of each key reaction step.

Citation

Senior, A., & Ball, L. T. (2021). Bismuth(V)-Mediated C–H Arylation of Phenols and Naphthols. SYNLETT, 32(03), 235-240. https://doi.org/10.1055/s-0040-1706294

• Journal Article Type: Article
• Acceptance Date: Aug 18, 2020
• Online Publication Date: Sep 28, 2020
• Publication Date: 2021-02
• Deposit Date: Jun 25, 2021
• Publicly Available Date: Sep 29, 2021
• Journal: Synlett
• Print ISSN: 0936-5214
• Electronic ISSN: 1437-2096
• Publisher: Thieme Publishing
• Peer Reviewed: Peer Reviewed
• Volume: 32
• Issue: 03
• Pages: 235-240
• DOI: https://doi.org/10.1055/s-0040-1706294
• Keywords: Organic Chemistry
• Public URL: https://nottingham-repository.worktribe.com/output/4939468
• Publisher URL: https://www.thieme-connect.com/products/ejournals/abstract/10.1055/s-0040-1706294