Synthesis of a 4,6-disubstituted dibenzofuran beta-sheet initiator by reductive radical arylation of benzene.
[reaction: see text] Tributyltin hydride mediated addition of 3-iodosalicylaldehyde to benzene in the presence of catalytic benzeneselenol affords (1,4-cyclohexadien-3-yl)salicylaldehyde. Homologation of the aldehyde group is followed by cycloetherification with dimethyl dioxirane to give a 4,6-disubstituted tetrahydrodibenzofuran. Adjustment of oxidation states and introduction of a second chain by Wittig olefination affords the beta-sheet initiator, ethyl 4-(2-tert-butoxycarbonylaminoethyl)-6-dibenzofuranpropanoate.
Crich
David
D
Department of Chemistry, University of Illinois at Chicago, 845 West Taylor Street, Chicago, Illinois 60607-7061, USA. dcrich@uic.edu
Grant
Daniel
D
D000478:Alkylation; D001554:Benzene / Q000737:chemistry*; D001572:Benzofurans / Q000138:chemical synthesis*; D003500:Cyclization; D005609:Free Radicals / Q000737:chemistry; D008968:Molecular Conformation; D010084:Oxidation-Reduction
D001572:Benzofurans; D005609:Free Radicals; C023614:dibenzofuran; D001554:Benzene