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手性螯合物与非螯合物控制的烯基 sp³ C-H 键的立体选择性官能化反应。

Chelation versus Non-Chelation Control in the Stereoselective Alkenyl sp C-H Bond Functionalization Reaction.

机构信息

Department of Chemistry, University of Science and Technology of China, 96 Jinzhai Road, Hefei, Anhui, 230026, China.

Institute of Advanced Synthesis, Jiangsu National Synergetic Innovation Center for Advanced Materials, Nanjing Tech University, 30 South Puzhu Road, Nanjing, Jiangsu, 210009, China.

出版信息

Angew Chem Int Ed Engl. 2017 Apr 24;56(18):5091-5095. doi: 10.1002/anie.201700559. Epub 2017 Mar 30.

Abstract

A hydroxy group chelation-assisted stereospecific oxidative cross-coupling reaction between alkenes was developed under mild reaction conditions. In the presence of palladium catalyst, the alkenes tethered with hydroxy functionality can couple efficiently with electron-deficient alkenes to form the corresponding multi-substituted olefin products. The hydroxy group on the substrate could play dual roles in reaction, acting as the directing group for alkenyl C-H bond activation and controlling the stereoselectivity of the products.

摘要

发展了一种在温和反应条件下通过羟基金属螯合辅助的立体选择性氧化交叉偶联反应。在钯催化剂的存在下,与羟功能基键合的烯烃可以与缺电子烯烃有效地偶联,形成相应的多取代烯烃产物。底物上的羟基因子在反应中可以起到双重作用,既可以作为烯基 C-H 键活化的导向基团,又可以控制产物的立体选择性。

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