Ni-Catalyzed Suzuki-Miyaura Cross-Coupling of α-Oxo-Vinylsulfones to Prepare C-Aryl Glycals and Acyclic Vinyl Ethers,Journal of the American Chemical Society

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Ni-Catalyzed Suzuki-Miyaura Cross-Coupling of α-Oxo-Vinylsulfones to Prepare C-Aryl Glycals and Acyclic Vinyl Ethers
Journal of the American Chemical Society ( IF 14.4 ) Pub Date : 2019-04-26 , DOI: 10.1021/jacs.9b02312
Liang Gong ₁ , Hong-Bao Sun ₁ , Li-Fan Deng ₁ , Xia Zhang ₁ , Jie Liu ₁ , Shengyong Yang ₁ , Dawen Niu ₁

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We demonstrate that readily available and bench-stable α-oxo-vinylsulfones are competent electrophiles in Ni-catalyzed Suzuki-Miyaura cross-coupling reactions. The C-sulfone bond in the α-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 α-heteroatom in facilitating these transformations.

中文翻译：

镍催化 Suzuki-Miyaura 交叉偶联 α-氧代-乙烯基砜制备 C-芳基乙二醇和无环乙烯基醚

我们证明，在 Ni 催化的 Suzuki-Miyaura 交叉偶联反应中，容易获得且工作台稳定的 α-氧代乙烯基砜是有能力的亲电试剂。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-芳基乙二醇或无环乙烯基醚。这些反应在温和的条件下进行，并且可以耐受范围广泛的杂环和官能团。初步的机理研究揭示了 α-杂原子在促进这些转变中的重要性。

更新日期：2019-04-26

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