Isolation of a non-heteroatom-stabilized gold-carbene complex.

ABSTRACT

Gold-carbene complexes are essential intermediates in many gold-catalyzed organic-synthetic transformations. While gold-carbene complexes with direct, vinylogous, or phenylogous heteroatom substitution have been synthesized and characterized, the observation in the condensed phase of electronically non-stabilized gold-carbenes has so far remained elusive. The sterically extremely shielded, emerald-green complex [IPr**Au=CMes2](+)[NTf2](-) has now been synthesized, isolated, and fully characterized. Its absorption maximum at 642 nm, in contrast to 528 nm of the red-purple carbocation [Mes2CH](+), clearly demonstrates that gold is more than just a "soft proton".