An ionic liquid-tagged second generation Hoveyda–Grubbs ruthenium carbene complex as highly reactive and recyclable catalyst for ring-closing metathesis of di-, tri- and tetrasubstituted dienes

A second generation Hoveyda–Grubbs ruthenium carbene complex bearing an ionic liquid tag was prepared and shown to be a highly reactive catalyst for the ring-closing metathesis of di-, tri- and tetrasubstituted diene and enyne substrates in minimally ionic solvent systems ([Bmim]PF6/CH2Cl2, 1:9–1:1 v/v). Both the catalyst and the ionic liquid can be conveniently recycled and repeatedly reused (up to 17 cycles) with only a very slight loss of activity. The ionic liquid tag is crucial to the high level of recyclability of the catalyst since the original second generation Grubbs and Hoveyda–Grubbs catalysts rapidly lose their activity when recycled in the ionic liquid layer.

A Ru catalyst bearing an ionic liquid tag was prepared and shown to be highly reactive for the RCM of a variety of diene and enyne substrates in minimally ionic solvents ([Bmim]PF6/CH2Cl2, 1:9–1:1 v/v). Both the catalyst and the ionic liquid can be conveniently recycled and repeatedly reused (up to 17 cycles).Figure optionsDownload as PowerPoint slide