A variety of esters were converted to corresponding tellurol esters in moderate to good yields by the reaction with iBu2AlTenBu. This transesterification proceeds smoothly in nonpolar solvents. Aryl esters reacted efficiently in comparison with alkyl esters. Addition of a catalytic amount of PPh3 or ZnCl2 accelerated the reaction and improved the yields. Substituents on the oxygen of esters exert significant steric effects on this transesterification, but the reaction is insensitive to the steric bulkiness of substituents on the carbonyl carbon. Competitive reactions of substituted ethyl benzoates showed a small positive ϱ value of 0.43 against σ+.