An efficient synthesis of substituted chrysenes

Eccleshare, Lee; Selzer, Sean; Woodward, Simon

Abstract

Substituted chrysenes have been swiftly synthesised by the 6-endo-dig cyclisation of ethynylnaphthalenes using platinum(II) chloride. Cyclisation precursors were directly prepared from commercially available 2-bromoaldehydes in a telescoped synthetic procedure involving a Cannizzaro triggered cascade and subsequent dehydration and desilylation. This short synthetic procedure allows rapid access to derivatives of biologically active molecules with useful electronic properties.

Citation

Eccleshare, L., Selzer, S., & Woodward, S. (2017). An efficient synthesis of substituted chrysenes. Tetrahedron, 58(5), https://doi.org/10.1016/j.tetlet.2016.12.004

• Journal Article Type: Article
• Acceptance Date: Dec 2, 2016
• Online Publication Date: Dec 9, 2016
• Publication Date: Feb 1, 2017
• Deposit Date: Dec 12, 2016
• Publicly Available Date: Dec 12, 2016
• Journal: Tetrahedron
• Print ISSN: 0040-4020
• Electronic ISSN: 0040-4020
• Publisher: Elsevier
• Peer Reviewed: Peer Reviewed
• Volume: 58
• Issue: 5
• DOI: https://doi.org/10.1016/j.tetlet.2016.12.004
• Keywords: Polyaromatic hydrocarbon; Carbocyclisation; Microwave-assisted synthesis
• Public URL: https://nottingham-repository.worktribe.com/output/837154
• Publisher URL: http://www.sciencedirect.com/science/article/pii/S0040403916316306