Ru(0)-catalyzed C3-selective Coupling Reactions of Unsaturated 5-Membered Heterocycles with Methyl Methacrylate and Methacryl Amide

Abstract

C3-selective direct coupling reactions of unsaturated 5-membered heterocycles such as 2, 5-dihydrofuran, N-tosyl-2, 5-dihydropyrrole, and 3-sulfolene with methyl methacrylate or methacryl amide are catalyzed by [Ru(η6-naphthalene)(η4-bicyclo[3.3.1]nona-2, 6-diene)] (1b). As an application of this method, a pesticide lead, 2-methyl-3-(tetrahydrofuran-3-yl)propanamide (6ab) is prepared in 2 steps from 2, 5-dihydrofuran in 62% total yield.