Site-Selective and Stereoselective trans-Hydroboration of 1,3-Enynes Catalyzed by 1,4-Azaborine-Based Phosphine-Pd Complex.
| Autor: | Xu S; Department of Chemistry, Boston College , Chestnut Hill, Massachusetts 02467-3860, United States., Zhang Y; Department of Chemistry, Boston College , Chestnut Hill, Massachusetts 02467-3860, United States., Li B; Department of Chemistry, Boston College , Chestnut Hill, Massachusetts 02467-3860, United States., Liu SY; Department of Chemistry, Boston College , Chestnut Hill, Massachusetts 02467-3860, United States. |
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| Jazyk: | angličtina |
| Zdroj: | Journal of the American Chemical Society [J Am Chem Soc] 2016 Nov 09; Vol. 138 (44), pp. 14566-14569. Date of Electronic Publication: 2016 Nov 01. |
| DOI: | 10.1021/jacs.6b09759 |
| Abstrakt: | A concise synthesis of monobenzofused 1,4-azaborine phosphine ligands (Senphos) is described. These Senphos ligands uniquely support Pd-catalyzed trans-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 κ 2 -P-η 2 -BC coordination mode, and this isolated complex has been shown to serve as a competent catalyst for the trans-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. |
| Databáze: | MEDLINE |
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