The　first　example　of　site-selective　silylation　of　C(sp＜sup＞3＜/sup＞)-H　bonds　mediated　by　a　[1,5]-hydrogen　transfer　is　reported.　This　reaction　occurs　selectively　at　the　α-position　of　benzamides　with　a　combination　of　tert-butylmagnesium　chloride　and　a　catalytic　amount　of　4,4＇-di-tert-butylbipyridine　(dtbpy)　ligand　and　provides　a　facile　route　for　the　creation　of　biologically　interesting　α-sila　benzamides.　Late-stage　functionalization　of　the　incorporated　silyl　moieties　facilitates　the　synthesis　of　N-formyl,　cis-enamine,　β-hydroxyl,　amino,　and　pyrrole-containing　derivatives.