Green grow the diarylmethanes: Substituted arenes and heteroarenes can be easily benzylated in the presence of inexpensive and relatively nontoxic metal salts such as FeCl3 (see scheme). This arylation method with benzyl alcohols is a state‐of‐the‐art green route to diarylmethanes as water is the only by‐product.
Friedel-Crafts type benzylation of arenes and heteroarenes with benzylic acetates, alcohols, and carbonates is effectively promoted under mild reaction conditions using catalytic amounts of gold salts. The resulting 1,1-diarylalkanes and 1-aryl-1-heteroarylalkanes are obtained in high yields and with high selectivity. The utility of the method is demonstrated by a short synthesis of beclobrate {ethyl 2-[4-(4-chlorobenzyl)-phenoxy]-2-methylbutyrate (3)}, a fibric acid derivative.
Friedel–Crafts‐type benzylation of various aromatic and heteroaromatic compounds with benzylic acetates, alcohols, and carbonates was promoted under mild reaction conditions by a series of Rh, Ir, Pd, and Pt catalysts (see scheme; R1=H, Me; R2=H, Cl, MeO; R3=H, Ac, CO2Me). The desired products were obtained in high yields and with high selectivities.
Substituierte Arene und Heteroarene können einfach in Gegenwart katalytischer Mengen von billigen und relativ ungiftigen Eisensalzen wie FeCl3 in hohen Ausbeuten und mit hohen Selektivitäten benzyliert werden. Mit Benzylalkoholen werden Diarylmethane praktisch nebenproduktfrei erhalten (siehe Schema).
A series of novel Shiff bases (1a-h) was synthesized by condensation of pyridinecarboxaldehydes (1-4) with 3-and 4-trifluoromethylanilines (5, 6) in the presence of molecular sieves (4 Å ). It was found that AlCl 3 and AlBr 3 catalyzed the addition of Me 3 SiCN to the C=N bond of the imines obtained, whereas the other Lewis acids studied (YCl 3 , LaCl 3 , ZnI 2 ) were not active. The reactivity of the imines in the title reaction, on the whole, correlated with their basicity. Besides the addition giving the expected a-amino nitriles (2a,b,d-f,h), an unusual reaction leading to unsaturated nitriles (3a-h) was observed. The structures of saturated and unsaturated products 2d and 3c were determined by X-ray diffraction.
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