Boronic Acids: New Coupling Partners in Room-Temperature Suzuki Reactions of Alkyl Bromides. Crystallographic Characterization of an Oxidative-Addition Adduct Generated under Remarkably Mild Conditions
Jan H. Kirchhoff, Matthew R. Netherton, Ivory D. Hills and Gregory C. Fu*
*Department of Chemistry, Massachusetts Institute of Technology, Cambridge, Massachusetts 02139, Email: gcfmit.edu
J. H. Kirchhoff, M. R. Netherton, I. D. Hill, G. C. Fu, J. Am. Chem. Soc., 2002, 124, 13662-13663.
DOI: 10.1021/ja0283899 (free Supporting Information)
A versatile method has been developed for the cross-coupling of boronic acids with unactivated alkyl electrophiles at room temperature. It has been demonstrated that Pd(P(t-Bu)2Me)2 undergoes oxidative addition under surprisingly mild conditions and that the resulting adduct is sufficiently stable toward β-hydride elimination.
see article for more examples
B. Saito, G. C. Fu, J. Am. Chem. Soc., 2007, 129, 9602-9603.
F. González-Bobes, G. C. Fu, J. Am. Chem. Soc., 2006, 128, 5360-5361.