A simple one-pot procedure for the direct conversion of alcohols into alkyl nitriles using TsIm

作者：Rad Mohammad Navid Soltani^*; Khalafi Nezhad Ali; Behrouz Somayeh; Faghihi Mohammad All

来源：Tetrahedron Letters, 2007, 48(38): 6779-6784.

DOI：10.1016/j.tetlet.2007.07.091

• nitrite
• alcohol
• N-(p-toluenesulfonyl)imidazole (TsIm)
• triethylamine (TEA)
• tetrabutylammonium iodide (TBAI)

A convenient and efficient one-pot preparation of nitriles from alcohols using N-(p-toluenesulfonyl)imidazole (TsIm) is described. In this method, treatment of alcohols with a mixture of NaCN, TsIm and triethylamine in the presence of catalytic amounts of tetra-n-butylammonium iodide (TBAI) in refluxing DMF furnishes the corresponding alkyl nitriles in good yields. This methodology is highly efficient for various structurally diverse alcohols with selectivity for ROH: 1 degrees > 2 degrees > 3 degrees.

• 出版日期2007-9-17