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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)


Abstract

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.

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Alkyl-Alkyl Suzuki Cross-Couplings of Unactivated Secondary Alkyl Halides at Room Temperature

B. Saito, G. C. Fu, J. Am. Chem. Soc., 2007, 129, 9602-9603.

Amino Alcohols as Ligands for Nickel-Catalyzed Suzuki Reactions of Unactivated Alkyl Halides, Including Secondary Alkyl Chlorides, with Arylboronic Acids

F. González-Bobes, G. C. Fu, J. Am. Chem. Soc., 2006, 128, 5360-5361.


Key Words

Suzuki Coupling, Substituted Arenes


ID: J48-Y2002-1350