二氧化硫介导的导向基团辅助的C(sp)-H芳基磺酰化反应
Directing-Group-Assisted C(sp)-H Arylsulfonylation from Sulfur Dioxide.
作者信息
Zhu Tonghao, Wu Jie
机构信息
School of Pharmaceutical and Materials Engineering & Institute for Advanced Studies, Taizhou University, 1139 Shifu Avenue, Taizhou 318000, China.
State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032, China.
出版信息
Org Lett. 2020 Sep 18;22(18):7094-7097. doi: 10.1021/acs.orglett.0c02400. Epub 2020 Aug 28.
A straightforward and stereoselective preparation of ()-β-alkenyl sulfones through a reaction of -tosyl acrylamides, 1,4-diazabicyclo[2.2.2]octane-sulfur dioxide, and aryldiazonium tetrafluoroborates under copper catalysis is accomplished. The direct C(sp)-H arylsulfonylation of acrylamides using sulfur dioxide as the sulfonyl source in the presence of copper trifluoroacetate proceeds smoothly, giving rise to ()-β-alkenyl sulfones in good yields. During the reaction process, excellent regio- and stereoselectivities are observed.
通过在铜催化下，使对甲苯磺酰基丙烯酰胺、1,4 - 二氮杂双环[2.2.2]辛烷 - 二氧化硫和四氟硼酸芳基重氮盐反应，实现了对（）-β-烯基砜的直接且立体选择性的制备。在三氟乙酸铜存在下，以二氧化硫作为磺酰基源，丙烯酰胺的直接C(sp) - H芳基磺酰化反应顺利进行，以良好的产率得到（）-β-烯基砜。在反应过程中，观察到了出色的区域选择性和立体选择性。
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