Ni-Catalyzed Suzuki-Miyaura Cross-Coupling of α-Oxo-vinylsulfones To Prepare C-Aryl Glycals and Acyclic Vinyl Ethers
Ni-Catalyzed Suzuki-Miyaura Cross-Coupling of α-Oxo-vinylsulfones To Prepare C-Aryl Glycals and Acyclic Vinyl Ethers
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Ni 催化 α-氧代-乙烯基砜的 Suzuki-Miyaura 交叉偶联制备 C-芳基二醇和无环乙烯基醚
DOI：
10.1021/jacs.9b02312
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发表时间：
2019-05-15
影响因子：
15
通讯作者：
Niu, Dawen
中科院分区：
文献类型：
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作者：
Gong, Liang;Sun, Hong-Bao;Niu, Dawen
我们证明，容易获得的和工作台稳定的α-氧代-乙烯基砜在Ni催化的铃木-宫浦交叉偶联反应中是称职的亲电试剂。在这些反应中，α-氧代-乙烯基砜基序中的C-砜键被化学选择性地裂解，以高产率提供C-芳基糖醛或无环乙烯基醚。这些反应在温和的条件下进行，并容忍显着范围的杂环和官能团。初步的机理研究揭示了α-杂原子在促进这些转化中的重要性。
We demonstrate that readily available and bench-stable alpha-oxo-vinylsulfones are competent electrophiles in Ni-catalyzed Suzuki-Miyaura cross-coupling reactions. The C-sulfone bond in the alpha-oxo-vinylsulfone motif is cleaved chemoselectively in these reactions, furnishing C-aryl glycals or acyclic vinyl ethers in high yields. These reactions proceed under mild conditions and tolerate a remarkable scope of heterocycles and functional groups. Preliminary mechanistic studies revealed the importance of an alpha-heteroatom in facilitating these transformations.