A rapid and efficient synthetic route to terminal arylacetylenes by tetrabutylammonium hydroxide- and methanol-catalyzed cleavage of 4-aryl-2-methyl-3-butyn-2-ols

• Jie Li and
• Pengcheng Huang

Beilstein J. Org. Chem. 2011, 7, 426–431, doi:10.3762/bjoc.7.55

• reaction time under much milder conditions. Keywords: 4-aryl-2-methyl-3-butyn-2-ol; deprotection reaction; 2-methyl-3-butyn-2-ol; terminal alkynes; tetrabutylammonium hydroxide; Introduction Terminal arylacetylenes are key precursors for the construction of conjugated oligo- or polyarylacetylenes, which

• Bu4NOH as base with CH3OH in toluene: Under a nitrogen atmosphere, 4-aryl-2-methyl-3-butyn-2-ol (2 mmol) was dissolved into anhydrous toluene (100 mL) and the solution was heated to 75 °C, then Bu4NOH, 40 wt % solution in CH3OH (Bu4NOH: 0.1 mol per 1 mol 2-hydroxypropyl group) was added. The mixture was