methanol; sodium tetrahydroborate; NiII chloride hexahydrate T=20°C; 0.0833333 h; chemoselective reaction;

1: 3-chloro-benzaldehyde With 18-crown-6 ether; oxygen; 3,4-dmtz iodide; potassium carbonate in acetonitrile T=20°C; 0.5 h; 2: benzyl bromide in acetonitrile T=20°C;

1: benzyl alcohol With 1,8-diazabicyclo[5.4.0]undec-7-ene; 1,4-dimethyl-1H-1,2,4-triazol-4-ium iodide; benzylamine in tetrahydrofuran 0.0833333 h; Inert atmosphere; 2: 3-chloro-benzaldehyde With 3,3',5,5'-tetra-tert-butyl-4,4'-diphenoquinone in tetrahydrofuran T=20°C; 2 h; Inert atmosphere; chemoselective reaction;

N,N-dimethyl acetamide; trifluorormethanesulfonic acid; oxygen; palladium diacetate T=115°C; P=760.051 Torr; 24 h; Schlenk technique;

tetrabutyl-ammonium chloride; oxygen; sodium hydride; 1-n-butyl-3-methylimidazolium chloride in tetrahydrofuran; mineral oil T=20°C; P=760.051 Torr; 2 h; Green chemistry;

1: 98 percent / KSCOCH3; Triton X-405 / 150 °C 2: 70 °C View Scheme

T=70°C;