Transfer of organic groups to gold using organotin compounds

PhSnMe3 undergoes transmetallation with [AuCl(EPh3)] (E = P, As) in refluxing toluene forming [AuPh(EPh3)] and Me3SnCl. The analogous nBu derivative does not transmetallate, even under forcing conditions. Similarly, 1-(trimethylstannyl)naphthalene and 1-(trimethylstannyl)-8-iodonaphthalene react with [AuCl(PPh3)] to give good yields of the corresponding naphthylgold(I) complexes which were spectroscopically and structurally characterised.

PhSnMe3 undergoes transmetallation with [AuCl(EPh3)] (E = P, As) in refluxing toluene forming [AuPh(EPh3)] and Me3SnCl. 1-(Trimethylstannyl)naphthalene and 1-(trimethylstannyl)-8-iodonaphthalene react with [AuCl(PPh3)] to give good yields of the corresponding naphthylgold(I) complexes which were spectroscopically and structurally characterised.Figure optionsDownload as PowerPoint slideResearch highlights
► PhSnMe3 undergoes transmetallation with gold(I) phosphines under mild conditions.
► Naphthyl gold(I) complexes are readily accessible in good yields by this method.
► Iodo-functionalised naphthyl gold(I) complexes can be obtained only by this route