Ferric chloride-catalyzed decarboxylative alkylation of β-keto acids with benzylic alcohols

Photocatalytic Hydroacylation of Alkenes by Directly Using Acyl Oximes

“…The residue was purified by flash column chromatography (PE–PE/EtOAc = 9/1) to afford the desired products 3 . The data of known compounds 3 are consistent with the previous reports, and the copies of their 1 H NMR spectra are included in the Supporting Information.…”

“…5, 162.1, 148.8, 143.4, 136.4, 128.7, 128.0, 126.7, 123.8, 121.4, 48.5, 48.0, 30.6 7, 149.2, 147.8, 142.8, 139.4, 135.3, 128.8, 127.7, 126.8, 123.4, 47.9, 43.6, 36.7, 7. 2, 149.2, 147.8, 142.8, 139.5, 135.4, 128.8, 127.7, 126.8, 123.5, 48.3, 45.5, 43.5, 17.0, 13.6 149.3, 147.8, 142.8, 139.5, 135.4, 128.8, 127.7, 126.8, 123.4, 48.3, 43.5, 43.3, 25.6, 22.2, 13.8 9, 149.3, 147.8, 142.8, 139.5, 135.4, 128.8, 127.7, 126.8, 123.4, 52.6, 48.7, 43.5, 24.4, 22.4, 22. 4,4-Diphenylbutan-2-one (3f). 16a Following the general procedure, 37.2 mg of 3f was isolated by FC on silica (PE/EtOAc 19/1) in 83% yield as yellow oil; 1 H NMR (400 MHz, chloroform-d) δ 7.29− 7.14 (m, 10H), 4.58 (t, J = 7.6 Hz, 1H), 3.17 (d,J = 7.6 Hz,2H), 2.07 (s, 3H); 13 C{ 1 H} NMR (100 MHz,143.9,128.6,127.7,126.5,49.7,46.1,butan-2-one (3g). 16a Following the general procedure, 27.4 mg of 3g was isolated by FC on silica (PE/EtOAc 19/1) in 58% yield as yellow oil; 1 H NMR (400 MHz, chloroform-d) δ 7.…”

“…4,butan-2-one (3n). 20 Following the general procedure, 26.3 mg of 3n was isolated by FC on silica (PE/EtOAc 19/1) in 45% yield as yellow oil; 1 H NMR (400 MHz, chloroform-d) δ 7.24 (d,J = 8.5 Hz,4H),7.11 (d,J = 8.4 Hz,4H), 4.54 (t, J = 7.5 Hz, 1H), 3.13 (d, J = 7.5 Hz, 2H), 2.09 (s, 3H); 13 C{ 1 H} NMR (100 MHz, chloroform-d) δ 206.0, 141. 9, 132.5, 129.0, 128.8, 49.3, 44.6, 30.7. 4-(4-Fluorophenyl)-4-phenylbutan-2-one (3o).…”

Iron Catalysis in Organic Synthesis

“…55 Jana and co-workers utilized benzylic alcohols as electrophiles for S N reactions with carboxamides and sulfonamides using iron(III) chloride as catalyst (Scheme 3). 56 This transformation proceeded in nitromethane, either at room temperature or at reflux affording benzylated amides in good to excellent yields.…”

Iridium-catalyzed regioselective decarboxylative allylation of β-ketoacids: efficient construction of γ,δ-unsaturated ketones

“…As the precursors of methyl ketones, b-ketoacids could act as stabilized ketone enolates and react with suitable electrophilic substrates. In fact, a series of electrophiles, such as imines, 4 aldehydes, 5 ketones, 6 alcohols, 7 sulfonamides, 8 allylic acetates, 9 isatins, 10 and activated alkenes 11 has been proved to be good reaction partners under certain conditions. Very recently, Breit's group reported a rhodium-catalyzed regioselective decarboxylative addition between b-ketoacids and terminal allenes to generate a series of g,d-unsaturated ketones.…”