Z. Song, H. Wong
Aug 1, 1995
Citations
0
Influential Citations
9
Citations
Journal
Journal of The Chinese Chemical Society
Abstract
Tris[4-(substituted)furan-3-yl]boroxines 2, prepared from the corresponding 4-(substituted)-3-(trimethylsilyl) furan 1, were converted successfully to 4-(substituted)-3-(tributylstannyl)furans 3 through palladium-catalyzed cross-coupling reactions with tributylstannyl chloride. Palladium-catalyzed cross-coupling reactions of 3 with organohalides afforded 3,4-disubstituted furans 4. Regiospecific iodination of 4-(trimethylsilyl)-3-((tributylstannyl) furan (3a) gave 4-iodo-3-(trimethylsilyl)furan (5), which reacted with excess ethyl acrylate under a common Heck-condition to produce 2,3-bis(trans-ethoxycarbonylvinyl)-4-(trimethylsilyl)furan (6). A thermal 6-electrocyclic reaction followed by dehydration converted 6 into benzo[2,3-6]furan 8. Oxidation of 2 generated the corresponding 4-substituted-3(2H)-furanones 9.