Cleavage of X−H Bonds (X = N, O, or C) by Copper(I) Alkyl Complexes To Form Monomeric Two-Coordinate Copper(I) Systems

The monomeric copper(I) alkyl complexes (IPr)Cu(R) [R = Me or
Et; IPr = 1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene] react with
substrates that possess N−H, O−H, and acidic C−H bonds to form
monomeric systems of the type (IPr)Cu(X) (X = anilido, phenoxide,
ethoxide, phenylacetylide, or N-pyrrolyl) and methane or ethane.
Solid-state X-ray crystal structures of the anilido, ethoxide, and
phenoxide complexes confirm that they are monomeric systems.
Experimental studies on the reaction of (IPr)Cu(Me) and aniline
to produce (IPr)Cu(NHPh) suggest that a likely reaction pathway
is coordination of aniline to Cu(I) followed by proton transfer to
produce methane and the copper(I) anilido complex.