Synthesis of highly oxygenated dinaphthyl ethers via SNAr reactions promoted by Barton's base.
[reaction: see text] Electron-rich dinaphthyl ethers were synthesized by S(N)Ar reactions between naphthols and activated fluoronaphthalenes. 2-tert-Butyl-1,1,3,3-tetramethylguanidine (Barton's base) was found to be an excellent, mild alternative to traditional inorganic bases for promoting the coupling reaction.
Wipf
Peter
P
Department of Chemistry, University of Pittsburgh, Pittsburgh, Pennsylvania 15260, USA. pwipf+@pitt.edu
Lynch
Stephen M
SM
D004987:Ethers / Q000138:chemical synthesis* / Q000737:chemistry*; D019791:Guanidine / Q000031:analogs & derivatives / Q000737:chemistry*; D006576:Heterocyclic Compounds, 4 or More Rings / Q000138:chemical synthesis; D015394:Molecular Structure; D009281:Naphthalenes / Q000737:chemistry; D009284:Naphthols / Q000737:chemistry*; D010100:Oxygen / Q000737:chemistry*; D013141:Spiro Compounds
D004987:Ethers; D006576:Heterocyclic Compounds, 4 or More Rings; D009281:Naphthalenes; D009284:Naphthols; D013141:Spiro Compounds; C476505:butyl-1,1,3,3-tetramethylguanidine; C462859:palmarumycin CP2; C042963:1-fluoronaphthalene; D019791:Guanidine; D010100:Oxygen