168064-07-1Relevant articles and documents
Half-sandwich ruthenium(II) catalysts for C-C coupling reactions between alkenes and diazo compounds
Baratta, Walter,Herrmann, Wolfgang A.,Kratzer, Roland M.,Rigo, Pierluigi
, p. 3664 - 3669 (2000)
The complex [(η5-C5H5)Ru(PPh3) 2Cl] (1) and other readily available ruthenium(II) derivatives of general formula [(η5-ligand)Ru(PR3)2X] efficiently catalyze the cyclopropanation of styrene and other electron-rich alkenes in the presence of ethyl diazoacetate with a high cis stereoselectivity. When diphenyldiazomethane is employed as carbene source, the reaction with styrene, catalyzed by 1, affords mainly 1,1,3-triphenylpropene, as result of a formal :CPh2-:CHCH2Ph coupling. Furthermore, appreciable amounts of the metathesis and, cyclopropanation products 1,1-diphenylethene and 1,2-diphenylcyclopropanes in a 1,1 molar ratio are observed. The carbene complex [(η5-C5H5)Ru(=CPh2)(PPh 3)Cl] (13), which was detected during the catalytic process, can be readily obtained in 85% isolated yield from 1 and diphenyldiazomethane in a one-pot reaction. With styrene, complex 13 undergoes a stoichiometric carbene transfer reaction, yielding the same organic products observed in the catalytic process with 1.