Add time:08/04/2019         Source:sciencedirect.com

Publisher SummaryFuran-containing molecules are found in both natural products and pharmaceuticals. At one time, furfural was produced in great quantities from corncobs. Perillene, a secondary plant metabolite, is an example of naturally occurring furan. Furan is frequently used as a bioisostere of a benzene ring in medicinal chemistry. Furan is a π-electron-excessive heteroarene. Electrophilic substitution and metalation take place regioselectively at C (2) due to the electronegativity of the oxygen atom. In comparison to the sulfur atom in thiophene, the oxygen in furan has higher electronegativity. Therefore, the lone pair of electrons on the oxygen are less effectively incorporated into the aromatic system, which contributes to the pronounced difference of reactivity of the α- and β-positions. In the context of palladium chemistry, furan and indole are the two classes of heterocycles that have attracted most attention. The synthesis of benzofurans and indoles using palladium chemistry has been a very active and prolific field. Contrary to all-carbon aryl halides, regioselective coupling reactions are routinely accomplished at C(2) for a 2,3-dihalofuran derivative. However, unlike 2-chloropyridines (an electron-deficient heterocycle), 2-chlorofurans are not sufficiently activated to add oxidatively to Pd (0).

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