A catalytic reaction of 3b, two equiv. of phenyl silane, and 10 mol% 1, led to the formation of a mixture of the hydrosilylated products 10a and 10b in near quantitative yield (Figure ). The reaction did not proceed in the absence of 1. Following the reaction as a function of time strongly suggests that 10a is a kinetic product that undergoes a second intramolecular hydrosilylation to give the 1-phenyl-1-silacyclohexane 10b. 10b could be isolated following column chromatography in 83% yield. 6b was observed spectroscopically during the reaction procedure, DFT Calculations: DFT calculations using the B97X-D 31 functional were used to gain further insight into the hydrometallation and -alkyl migration step. A model was developed to explain the effect of both the cycloalkane ring-size and nature of the metal on reactivity. Methods were benchmarked against the solid state structures and the activation parameters from kinetics data (vide supra). Metal atoms (Mg, Zn) were described with Stuggart SDDAll RECPs and associated basis sets, while a hybrid basis set was used for the other atoms: 6-31g**(C, H)/ 6-311+g*(N, O). Complete potential energy surfaces for reactions of 1 and 2 with 3a-d, along with functional testing and computational details, can be found in the supporting information.