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Use of tunable ligands allows for intermolecular Pd-catalyzed C--O bond formation.

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      Abstract

      Bulky biaryl phosphine ligands facilitate Pd-catalyzed C-O coupling reactions of aryl halides with primary and secondary alcohols by promoting reductive elimination at the expense of beta-hydride elimination. The key to their success is the ability to match the size of the ligand to that of the combination of substrates. The efficient coupling of a number of unactivated aryl chlorides and bromides with cyclic and acyclic secondary alcohols was achieved. This included the coupling of allylic alcohols for the first time in a Pd-catalyzed coupling process.

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      Affiliations
      [1 ] Department of Chemistry, Massachusetts Institute of Technology, Cambridge, Massachusetts 02139, USA.
      Journal
      J. Am. Chem. Soc.
      Journal of the American Chemical Society
      American Chemical Society (ACS)
      0002-7863
      0002-7863
      Jun 08 2005
      : 127
      : 22
      15926842
      10.1021/ja050471r

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