2-Iodoadenosine

Typical procedure: 2-Iodoadenosine (393 mg), CuI (9.5 mg), bis(triphenylphosphine)palladium(II) dichloride (36 mg), triethylamine (0.16 mL) and ethynylbenzene (123 mg) in DMF (7 mL) is heated 80 °C for 1 h. After 2-iodoadenosine is completely consumed, the reaction mixture is concentrated to dryness under reduce pressure. The residue is dissolved in CHCl3, and H2S gas is introduced to the solution (~30 s) followed by N2 gas. The suspension is filtered through a Celite pad and washed with CHCl3. The combined filtrate is concentrated to dryness in vacuo, and the residue is purified by a silica gel column chromatography (eluent: MeOH–CHCl3) to give 2-(phenylethyn-1-yl)adenosine (373 mg, 97 %).