格氏试剂促进的脱磺酰化/分子内偶联反应合成2-(1-氟乙烯基)吡啶
Grignard-Reagent-Promoted Desulfonylation/Intramolecular Coupling for the Synthesis of 2-(1-Fluorovinyl)pyridines.
作者信息
Kang Lei, Zhang Jinlong, Yang Huameng, Qian Jinlong, Jiang Gaoxi
机构信息
State Key Laboratory for Oxo Synthesis and Selective Oxidation, Center for Excellence in Molecular Synthesis, Suzhou Research Institute of LICP, Lanzhou Institute of Chemical Physics (LICP), Chinese Academy of Sciences, Lanzhou 730000, People's Republic of China.
University of Chinese Academy of Sciences, Beijing 100049, People's Republic of China.
出版信息
Org Lett. 2020 Nov 20;22(22):9118-9122. doi: 10.1021/acs.orglett.0c03521. Epub 2020 Nov 4.
A novel process involving Grignard-reagent-promoted desulfonylation/intramolecular coupling of readily available α-fluoro-α,β-unsaturated-(2-pyridyl)sulfones was realized that provided a series of polysubstituted 2-(1-fluorovinyl)pyridines in good yields. The intrinsic coordination between pyridine and Mg(II) along with the "negative fluorine effect" of the substrates should play the key role for the smooth transformation in the absence of transition-metal catalysts.
实现了一种新颖的方法，该方法涉及格氏试剂促进的易于获得的α-氟-α,β-不饱和-(2-吡啶基)砜的脱磺酰化/分子内偶联反应，能以良好的产率提供一系列多取代的2-(1-氟乙烯基)吡啶。吡啶与Mg(II)之间的固有配位作用以及底物的“负氟效应”在无过渡金属催化剂的情况下对顺利转化应起关键作用。
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