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With n-butyllithium; 3-(4-hydroxybutyl)-1-mesityl-4,5-dihydro-1H-imidazol-3-ium hexafluorophosphate; hydrogen; copper(l) chloride; In tetrahydrofuran; at 60℃; under 37503.8 Torr; for 18h;Autoclave;
General procedure: A 5 mL glass vial was charged with CuCl (0.02 mmol, 5 mol%) and ligand precursor 5c (0.03 mmol, 7.5 mol%). The vial was evacuated and refilled with N2 (3 ×). THF was added (1 mL for solid substrates; 1.5mL for liquid substrates), the mixture was stirred for 2 min at r.t. followed by the addition of n-BuLi (0.06 mmol, 15 mol%). The resulting mixture was stirred for 2 min at r.t. before the addition of the corresponding internal alkyne 10 (solid substrates were added as a solutionin 0.5 mL THF, liquid substrates were added neat). The rubber septum was punctured with a needle, the vial was placed in an autoclave and the mixture stirred (750 rpm) under H2 pressure (50 bar, unless otherwise noted). After completion of the reaction, all volatiles were removed under reduced pressure and the crude mixture was purified by column chromatography to give the desired product 11.
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