Solvent-Free Organic Transformations with Amberlite IRA900F

Significance

A variety of organic transformations with Amberlite IRA900F (Amb-F) as a metal-free catalyst for the activation of Si-N and Si-O bonds and a mild base under solvent-free conditions is described. Thus, Amb-F was applied to (1) the [3+2] cycloaddition of nitroalkenes 1 with TMSN₃ 2, (2) the 1,3-dipolar cycloaddition of aryl nitriles 4 and 2, (3) the Michael addition of 2 to α,β-unsaturated carboxylic acids and esters 6, (4) the Michael addition of ketene silyl acetal 9 to nitroalkenes 8, and (5) the Michael addition of ethyl nitroacetate 11 onto 8 under solvent-free conditions, to give the corresponding adducts in 70-96% yield.