Henan Key Laboratory of Organic Functional Molecules and Drug Innovation, Key Laboratory for Yellow River and Huai River Water Environmental Pollution Control, Ministry of Education, Collaborative Innovation Center of Henan Province for Green Manufacturing of Fine Chemicals, School of Environment, School of Chemistry and Chemical Engineering, Henan Normal University, Xinxiang, Henan 453007, China.
J Org Chem. 2020 Dec 4;85(23):15600-15609. doi: 10.1021/acs.joc.0c02368. Epub 2020 Nov 12.
An efficient synthesis of β-methylsulfonylated N-heterocycles FeCl-catalyzed C(sp)-H dehydrogenation and C(sp)-H methylsulfonylation of inactivated cyclic amines with the promotion and participation of inorganic sodium metabisulfite and dicumyl peroxide (DCP) has been developed. Notably, bifunctional DCP acted not only as an oxidant to promote the dehydrogenation but also as a methyl radical to participate in the sulfone formation. With this protocol, a number of β-methylsulfonylated tetrahydropyridines, tetrahydroazepines, and pyrroles were obtained in a facile one-pot manner.
已开发出一种高效合成β-甲基亚磺酰基 N-杂环的方法：在 FeCl 催化下，在无机亚硫酸钠和过氧化二异丙苯（DCP）的促进和参与下，对失活环状胺进行 C(sp)-H 脱氢和 C(sp)-H 甲基亚磺酰化。值得注意的是，双功能 DCP 不仅用作氧化剂以促进脱氢，而且用作甲基自由基以参与砜的形成。通过该方案，以简便的一锅法获得了多种β-甲基亚磺酰基四氢吡啶、四氢氮杂环庚烷和吡咯。
