The reaction of SnC(SiMe3)2CH2CH 2C(SiMe3)2/ArI (Ar = Ph, 2,4,6- triisopropylphenyl) with cyclohexane, diethyl ether, tetrahydrofuran (THF), toluene, and mesitylene yields C-H activation products in which a new Sn-C bond is formed at the location of the weakest C-H bond. The regioselectivity of this reaction with trans-4-methyl-2-pentene and 4-methyl-2-pentyne was explored as a function of aryl halide for PhI, 2,4,6-trimethyliodobenzene, 2,4,6-triisopropyliodobenzene, 4-iodoanisole, 4-iodobenzonitrile, and 2,6-mesityliodobenzene. A degree of regiochemical control could be obtained as highlighted by increased amounts of primary activation. The use of 2,4,6-tert-butyliodobenzene resulted in C-H activation of the ortho tert-butyl groups in all solvents tried. The primary kinetic isotope effect for the reaction of SnC(SiMe3)2CH2CH 2C(SiMe3)2/2,4,6-triisopropyliodobenzene with toluene/toluene-d7 was found to be 4.9 ± 0.5.