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Base-Promoted Coupling of HFIP in Cu-Catalyzed Asymmetric Ring Opening of Cyclic Diaryliodoniums
The Journal of Organic Chemistry ( IF 3.3 ) Pub Date : 2024-11-11 , DOI: 10.1021/acs.joc.4c02426 Abdur Rahim, Biqiong Hong, Zhenhua Gu
The Journal of Organic Chemistry ( IF 3.3 ) Pub Date : 2024-11-11 , DOI: 10.1021/acs.joc.4c02426 Abdur Rahim, Biqiong Hong, Zhenhua Gu
We report a Cu-catalyzed asymmetric ring-opening reaction of cyclic diaryliodoniums with 1,1,1,3,3,3-hexafluoroisopropanol (HFIP), enabling the construction of axially chiral biaryl compounds containing HFIP ether. HFIP is highly polar and exceptionally stable; thus, it is commonly used as a solvent due to its poor nucleophilicity. However, its use as a nucleophilic reagent has been rare. In this study, we successfully employed HFIP as a nucleophilic coupling partner in a Cu-catalyzed asymmetric ring-opening experiment of cyclic diaryliodoniums.
中文翻译:
HFIP 在铜催化的环状二芳基糖铵不对称开环中的碱促进偶联
我们报道了环状二芳基鎓与 1,1,1,3,3,3-六氟异丙醇 (HFIP) 的 Cu 催化不对称开环反应,能够构建含有 HFIP 醚的轴向手性联芳基化合物。HFIP 具有强极性且非常稳定;因此,由于其亲核性差,它通常用作溶剂。然而,它作为亲核试剂的用途很少见。在这项研究中,我们成功地将 HFIP 用作环状二芳基铵的不对称开环实验中的亲核偶联伴侣。
更新日期:2024-11-12
中文翻译:
HFIP 在铜催化的环状二芳基糖铵不对称开环中的碱促进偶联
我们报道了环状二芳基鎓与 1,1,1,3,3,3-六氟异丙醇 (HFIP) 的 Cu 催化不对称开环反应,能够构建含有 HFIP 醚的轴向手性联芳基化合物。HFIP 具有强极性且非常稳定;因此,由于其亲核性差,它通常用作溶剂。然而,它作为亲核试剂的用途很少见。在这项研究中,我们成功地将 HFIP 用作环状二芳基铵的不对称开环实验中的亲核偶联伴侣。