‘Green’ methodology for efficient and selective benzoylation of nucleosides using benzoyl cyanide in an ionic liquid

Benzoyl cyanide in the ionic liquid 1-methoxyethyl-3-methylimidazolium methanesulfonate has been employed as a ‘green’ alternative and mild reaction condition protocol to conventional pyridine–benzoyl chloride system for efficient and selective benzoylation of nucleosides (of both the ribo- and deoxyribo-series) at ambient temperatures. The use of benzoyl cyanide–ionic liquid combination has been successfully extended for highly efficient benzoylation of phenols, aromatic amines, benzyl alcohol, aliphatic diols, 3-aminophenol and 2-aminobenzylalcohol, which indicates the versatility of this benzoylating system.

Efficient benzoylation of various nucleosides (both ribo- and 2′-deoxyribo), phenols, aromatic amines, benzyl alcohol, aliphatic diols, 3-aminophenol and 2-aminobenzylalcohol has been accomplished using benzoyl cyanide in ionic liquid 1-methoxyethyl-3-methylimidazolium methanesulfonate with catalytic amount of DMAP under ambient conditions.Figure optionsDownload as PowerPoint slide