Anion influences on the structures of pyridyl-iminosulfonate copper(II) complexes and their reactivity in Chan–Lam couplings

Abstract

Reaction of pyridylcarbaldehyde with taurine or orthanilic acid in the presence of copper salts provided copper complexes (PyC(H)N-CxHy-SO3)CuX with X = chloride, nitrate, acetate, or triflate and CxHy = o-C6H4 or C2H4. All complexes were characterized by single crystal X-ray diffraction and formed either mononuclear water adducts, dimeric complexes, or one-dimensional coordination polymers. Activities in the Chan–Lam coupling of aniline with phenylboronic acid varied by less than a factor of two between catalysts with various anions, supporting previous mechanistic claims that the anion does not participate in the formation of copper–boron intermediates. There is no difference in the performance of a catalyst with an alkyl backbone, indicating that sulfonate dissociation is not part of the catalytic cycle.