Straightforward Synthesis of 2(5H)-Furanones as Promising Cross-Coupling Partners: Direct Furanone Annulation Utilizing Ti-Mediated Aldol Addition

Abstract

Direct 2(5H)-furanone annulation produces promising cross-coupling partners incorporating m-or p-bromo-and p-tosyloxyphenyl groups into the 5-position of a notable 2(5H)-furanone pharmacore. The present one-pot annulation method involves two distinctive reactions: (i) a powerful and crossed Ti-direct aldol addition and (ii) an acid-induced characteristic cyclocondensation, leading to 2(5H)-furanones. Suzuki-Miyaura cross-coupling of 5-(4-bromophenyl)-furan-2(5H)-ones, 5-(4-tosyloxyphenyl)-3,4-dimethylfuran-2(5H)-ones and a furan derivative successfully afforded the corresponding products with the 2(5H)-furanone skeleton.

Comparative studies of palladium and copper-catalysed γ-arylation of silyloxy furans with diaryliodonium salts

“…8, 147.72, 137.46, 132.20, 130.53, 130.01, 129.41, 125.03, 81.10, 29.72, 10.69. Spectral data matched literature sources [51]. Prepared according to General Procedure C using (Mesityl-I-4-Bromophenyl)PF 6 with 5 mol % Cu(OTf) 2 and 5 mol % PhBox for 16 h. Reaction was run on 0.165 mmol (90.3 mg) scale.…”