dichloro bis(acetonitrile) palladium(II); oxygen; copper(l) chloride in water; N,N-dimethyl-formamide Wacker oxidation;

1.1: 85 percent / m-chloroperbenzoic acid; acetic acid / CH2Cl2 / 24 h / Heating 2.1: N,O-dimethylhydroxylamine hydrochloride; methyllithium / tetrahydrofuran / 0 - 20 °C 2.2: tetrahydrofuran / 0 - 20 °C 3.1: 2.54 g / imidazole / tetrahydrofuran / 2 h View Scheme

1.1: N,O-dimethylhydroxylamine hydrochloride; methyllithium / tetrahydrofuran / 0 - 20 °C 1.2: tetrahydrofuran / 0 - 20 °C 2.1: 2.54 g / imidazole / tetrahydrofuran / 2 h View Scheme

1H-imidazole in tetrahydrofuran 2 h;

1: sodium hydride / tetrahydrofuran 2: 2,2'-azo-bisisobutyronitrile; tri-n-butyl-tin hydride / toluene 3: dichloro bis(acetonitrile) palladium(II); oxygen; copper(l) chloride / water; N,N-dimethyl-formamide View Scheme

1: 2,2'-azo-bisisobutyronitrile; tri-n-butyl-tin hydride / toluene 2: dichloro bis(acetonitrile) palladium(II); oxygen; copper(l) chloride / water; N,N-dimethyl-formamide View Scheme

1: 1H-imidazole; 4-(N,N-dimethlyamino)pyridine 2: dimethylsulfide borane complex; dihydrogen peroxide; sodium hydroxide / tetrahydrofuran 3: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide 4: diethyl ether 5: sodium hydride / tetrahydrofuran 6: 2,2'-azo-bisisobutyronitrile; tri-n-butyl-tin hydride / toluene 7: dichloro bis(acetonitrile) palladium(II); oxygen; copper(l) chloride / water; N,N-dimethyl-formamide View Scheme

1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide 2: diethyl ether 3: sodium hydride / tetrahydrofuran 4: 2,2'-azo-bisisobutyronitrile; tri-n-butyl-tin hydride / toluene 5: dichloro bis(acetonitrile) palladium(II); oxygen; copper(l) chloride / water; N,N-dimethyl-formamide View Scheme

1: 1H-imidazole; 4-(N,N-dimethlyamino)pyridine 2: dimethylsulfide borane complex; dihydrogen peroxide; sodium hydroxide / tetrahydrofuran 3: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide 4: diethyl ether 5: sodium hydride / tetrahydrofuran 6: 2,2'-azo-bisisobutyronitrile; tri-n-butyl-tin hydride / toluene 7: dichloro bis(acetonitrile) palladium(II); oxygen; copper(l) chloride / water; N,N-dimethyl-formamide View Scheme

1: diethyl ether 2: sodium hydride / tetrahydrofuran 3: 2,2'-azo-bisisobutyronitrile; tri-n-butyl-tin hydride / toluene 4: dichloro bis(acetonitrile) palladium(II); oxygen; copper(l) chloride / water; N,N-dimethyl-formamide View Scheme