Department of Emergency, State Key Laboratory of Biotherapy and Cancer Center, West China Hospital, and School of Chemical Engineering , Sichuan University , Chengdu 610041 , China.
J Am Chem Soc. 2019 May 15;141(19):7680-7686. doi: 10.1021/jacs.9b02312. Epub 2019 May 2.
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.
我们证明了 readily available 和 bench-stable 的 α-oxo-vinylsulfones 是 Ni 催化的 Suzuki-Miyaura 交叉偶联反应中有效的亲电试剂。在这些反应中，α-氧代乙烯砜结构中的 C-砜键被选择性地切断，以高产率得到 C-芳基糖醛或非环乙烯基醚。这些反应在温和的条件下进行，并能容忍显著范围的杂环和官能团。初步的机理研究表明，α-杂原子在促进这些转化中的重要性。
