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      Ligand-accelerated cross-coupling of C(sp2)-H bonds with arylboron reagents.

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          Abstract

          A ligand-accelerated Pd(II)-catalyzed C(sp(2))-H/arylboron cross-coupling reaction of phenylacetic acid substrates is reported. Using Ac-Ile-OH as the ligand and Ag(2)CO(3) as the oxidant, a fast, high-yielding, operationally simple, and functional group-tolerant protocol has been developed for the cross-coupling of phenylacetic acid substrates with aryltrifluoroborates. This ligand scaffold has also been shown to improve catalysis using 1 atm O(2) as the sole reoxidant, which sheds light on the path forward in developing optimized ligands for aerobic C-H/arylboron cross-coupling.

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          Author and article information

          Journal
          J. Am. Chem. Soc.
          Journal of the American Chemical Society
          1520-5126
          0002-7863
          Nov 16 2011
          : 133
          : 45
          Affiliations
          [1 ] Department of Chemistry, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, California 92037, United States.
          Article
          NIHMS334020
          10.1021/ja203978r
          21913636
          beb9fc52-38a9-4ad3-8cd4-5a202acaedd4
          History

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