N-heterocyclic carbenes (NHC) are strong Lewis bases that have demonstrated broad utility as ligands for transition metal (TM) catalysts. Silicon analogues, N-heterocyclic silylenes (NHSi), are comparatively less well studied. The decreased [Pi]-[pi] overlap between the Si 3p orbital and adjacent nitrogen lone pairs creates a more accessible vacant orbital on Si, resulting in increased ambiphilic character. When bound to a transition metal, this empty orbital presents an opportunity to cooperatively bind and activate substrate molecules. To increase the stability of a potential metal-silylene complex we targeted the diphosphine ligand precursor 1,2-bis(R2PCH2NCH2)C6H4 (R = alkyl or aryl), first reported by Yamashita and Nozaki in the construction of a boron-anchored pincer. Reported here are (PCy)2Si pincer ligands and their TM-silylene complexes for small molecule activation.