Two-metal dual activation represents the combination of the enolate activation mode and the alkyne activation mode into a single reaction system. Generally, a hard, oxophilic metal (K, Na, Ag) activates the enolate oxygen, while a soft, carbophilic metal (Pd, Cu, Mo) coordinates with the alkyne. In some instances, however, the precise role of each metal is unclear. For example, in a 2005 study Toste et al. found that treatment of an alkynyl-tethered β-ketoester with a Pd(II) phosphine complex and Yb(OTf) effected asymmetric cyclization to the corresponding cyclopentane. It is proposed that a Pd-enolate adds into a Yb-activated alkyne, though there is also precedent for Pd activation of alkynes.