1: 2-(1-adamantyl)-4-bromo-1-methoxybenzene With n-butyllithium in tetrahydrofuran T=-75 - -70°C; 1 h; 2: tri-isopropoxy-borane in tetrahydrofuran T=-70 - 20°C; 3: With hydrogenchloride; water in tetrahydrofuran T=20°C;

1: With n-butyllithium in tetrahydrofuran; hexane T=-78°C; 0.0833333 h; 2: With boron triethoxide in tetrahydrofuran; hexane T=-78°C; 0.5 h; 3: With hydrogenchloride in tetrahydrofuran; hexane; water T=20°C;

1: 2-(1-adamantyl)-4-bromo-1-methoxybenzene With magnesium; ethylene dibromide in tetrahydrofuran RefluxInert atmosphere; 2: boric acid trimethyl ester in tetrahydrofuran T=-50 - -40°C; 0.5 h; Inert atmosphere; 3: With hydrogenchloride; water in tetrahydrofuran

magnesium; 1,2-dibromoethane; lithium chloride in tetrahydrofuran under Ar; Mg and LiCl in THF heated at 40°C, 1,2-Br2C2H4 added, 2-(1-adamantyl)-4-Br-anisole in THF added at slight boiling temp., boiling for 0.5 h, decantation, soln. added to soln. of B(OMe)3 in THF at 0-5°C, stored at 0°C (16 h); HCl and water added, mixt. extd. with Et2O, org. phase dried over Na2SO4, evapn. under vac., residue treated with EtOAc, soln. stored at 0°C overnight, ppt. filtered off, washed with cold EtOAc, dried at 100°C;

1: With potassium carbonate; palladium 10 on activated carbon in tetrahydrofuran; water 8 h; Heating / reflux; 2: With hydrogenchloride; water in tetrahydrofuran 1 h; Product distribution / selectivity;

2: sodium hydroxide / methanol / 8 h / Reflux View Scheme

1: With tris-(3-hydroxypropyl)-phosphine; nickel dichloride in tetrahydrofuran 1 h; Heating / reflux; 2: 3-(1-adamantyl)-4-methoxyphenylboronic acid; 2-methoxycarbonyl-6-(p-tolylsulfonyl)naphthalene With water; potassium carbonate in tetrahydrofuran T=50°C; 24 h; Heating / reflux; Product distribution / selectivity;

sodium carbonate; dicyclohexyl(2′,6′-dimethoxybiphenyl-2-yl)phosphine; tris-(dibenzylideneacetone)dipalladium(0) in tetrahydrofuran; water Suzuki-Miyaura cross-coupling; Inert atmosphereReflux; Product distribution / selectivity;