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      Site-Selective and Stereoselective trans-Hydroboration of 1,3-Enynes Catalyzed by 1,4-Azaborine-Based Phosphine–Pd Complex

      1 , 1 , 1 , 1
      Journal of the American Chemical Society
      American Chemical Society (ACS)

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          Abstract

          <p class="first" id="P1">A concise synthesis of monobenzofused 1,4-azaborine phosphine ligands (Senphos) is described. These Senphos ligands uniquely support Pd-catalyzed <i>trans</i>-selective hydroboration of terminal and internal 1,3-enynes to furnish corresponding dienylboronates in high efficiency and diastereoselectivity. X-ray structural analysis of the Senphos–Pd(0) complex reveals a <i>κ</i> <sup>2</sup>- <i>P</i>- <i>η</i> <sup>2</sup>-BC coordination mode, and this isolated complex has been shown to serve as a competent catalyst for the <i>trans</i>-hydroboration reaction. This work demonstrates that the expanded chemical space provided by the BN/CC isosterism approach translates into the functional space in the context of stereoselective catalytic transformations. </p>

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          Author and article information

          Journal
          Journal of the American Chemical Society
          J. Am. Chem. Soc.
          American Chemical Society (ACS)
          0002-7863
          1520-5126
          October 28 2016
          November 09 2016
          November 2016
          November 09 2016
          : 138
          : 44
          : 14566-14569
          Affiliations
          [1 ]Department of Chemistry, Boston College, Chestnut Hill, Massachusetts 02467-3860, United States
          Article
          10.1021/jacs.6b09759
          5591746
          27802037
          4c7a39d6-c53d-401b-a17a-90244acf5ed6
          © 2016
          History

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