50635-73-9Relevant articles and documents
Palladium-catalyzed suzuki-miyaura reaction involving a secondary sp 3 carbon: Studies of stereochemistry and scope of the reaction
Rodriguez, Nuria,De Arellano, Carmen Ramirez,Asensio, Gregorio,Medio-Simon, Mercedes
, p. 4223 - 4229 (2007)
Palladium-catalyzed C-C bond formation involving secondary sp 3-hybridized carbon is described. These reactions occur with secondary 1-bromoethyl arylsulfoxides and different arylboronic acids, to produce the corresponding arylated sulfoxides in moderate to high yields and with complete stereospecificity. Despite the presence of β hydrogens in the substrate, the competitive β-hydride elimination is not a significant side reaction when coordinating solvents are used. The reported cross-coupling involves secondary Csp3-Csp2 bond formation: this is the first time that a mechanistic study has been carried out with such substrates. The reaction proceeds with inversion of configuration at the stereogenic C sp3 carbon. The high stereospecificity of the coupling and the mildness of the reaction conditions allow for the preservation of the optical purities of reagents and products and the preparation of useful chiral targets.