title: Deoxygenative C-C Bond-Forming Processes via a Net Four-Electron Reductive Coupling.
abstract: The nickel-catalyzed coupling of enones or enals with alkynes in the presence of silane and titanium alkoxide reductants provides direct access to skipped diene products. The process involves a net four-electron reductive coupling and proceeds with deoxygenation of the starting enone or enal. A new class of well-defined nickel(0) precatalysts bearing an unhindered N-heterocyclic carbene ligand, which was developed in optimization of the process, is essential for the efficiency of the transformation. The strategy allows the high reactivity of α,β-unsaturated carbonyl substrates to be utilized in couplings with simultaneous extrusion of the oxygen atom, thus enabling a traceless strategy for alkene installation.
authors.affiliation: Department of Chemistry, University of Michigan , 930 North University Avenue, Ann Arbor, Michigan 48109-1055, United States.
authors.forename: David P
authors.initials: DP
authors.lastname: Todd
authors.affiliation: Department of Chemistry, University of Michigan , 930 North University Avenue, Ann Arbor, Michigan 48109-1055, United States.
authors.forename: Benjamin B
authors.initials: BB
authors.lastname: Thompson
authors.affiliation: Department of Chemistry, University of Michigan , 930 North University Avenue, Ann Arbor, Michigan 48109-1055, United States.
authors.forename: Alex J
authors.initials: AJ
authors.lastname: Nett
authors.affiliation: Department of Chemistry, University of Michigan , 930 North University Avenue, Ann Arbor, Michigan 48109-1055, United States.
authors.forename: John
authors.initials: J
authors.lastname: Montgomery