Tris(trimethylsilyl)methane is not an effective mediator of radical reactions

The reductive dehalogenation of organohalides by tris(trimethylsilyl)methane has been re-investigated. Contrary to claims made in a recent publication (Tetrahedron Lett. 2006, 47, 5163-5165), (TMS)CH does not reduce organohalides. In competition experiments between (TMS)CH and the poor chain mediator EtSiH, the latter performed the reduction. Computational investigations support these experimental findings and indicate that the C-H bond of (TMS)CH is too strong for this compound to serve as an effective mediator of radical reactions