Synthesis of 2,3-Dihydrobenzofuran.

Bakke, Jan M.; ROHOLDT, H. M.; Daasvatn, Kari; Forsgren, Björn; Gustafsson, Jan‐Åke; Högberg, B.; Becher, Jan

doi:10.3891/acta.chem.scand.34b-0073

Cited by 4 publications

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“…The dihydrobenzofuran unit is very common in natural products and biologically significant synthetic compounds . Previously developed methodology for the synthesis of dihydrobenzofurans has utilized the [3+2] cycloaddition of phenols to alkenes, the intramolecular acid-catalyzed cyclization of allylic phenols and quinines, and the electrophilic cyclization of 2-(2-hydroxyethyl)phenyl diazonium salts, as well as radical and transition metal-catalyzed cyclizations. Unfortunately, these methods are not very general and, in most cases, do not tolerate sensitive functional groups.…”

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Synthesis of Dihydrobenzofurans via Palladium-Catalyzed Annulation of 1,3-Dienes by o-Iodoaryl Acetates

Rozhkov

Larock

2010

J. Org. Chem.

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The palladium-catalyzed annulation of 1,3-dienes by o-iodoaryl acetates provides an efficient approach to biologically interesting dihydrobenzofurans. The annulation is believed to proceed via (1) oxidative addition of the aryl iodide to Pd(0), (2) syn-addition of the resulting arylpalladium complex to the 1,3-diene, (3) intramolecular coordination of the phenolic oxygen to the Pd center, (4) hydrolysis of the acetyl group, and (5) reductive elimination of Pd(0), which regenerates the catalyst. This reaction is quite general, regioselective, and stereoselective, and a wide variety of terminal, cyclic, and internal 1,3-dienes, as well as electron-rich and electron-deficient o-iodoaryl acetates, can be utilized.

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confidence: 99%