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高立体选择性的金催化重氮试剂与氟化烯醇硅醚对四取代烯烃的偶联反应。

Highly Stereoselective Gold-Catalyzed Coupling of Diazo Reagents and Fluorinated Enol Silyl Ethers to Tetrasubstituted Alkenes.

机构信息

Shanghai Key Laboratory of Green Chemistry and Chemical Processes, East China Normal University, 3663N Zhongshan Road, Shanghai, 200062, China.

State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Shanghai, 200032, China.

出版信息

Angew Chem Int Ed Engl. 2017 Feb 20;56(9):2459-2463. doi: 10.1002/anie.201611625. Epub 2017 Jan 18.

Abstract

We report a highly stereoselective synthesis of all-carbon or fluorinated tetrasubstituted alkenes from diazo reagents and fluorinated enol silyl ethers, using C-F bond as a synthetic handle. Cationic Au catalysis plays a key role in this reaction. Remarkable fluorine effects on the reactivity and selectivity was also observed.

摘要

我们报道了一种高立体选择性的合成方法,通过重氮试剂和氟化烯醇硅醚反应,利用 C-F 键作为合成手性,合成全碳或全氟取代的四取代烯烃。该反应中阳离子 Au 催化起到了关键作用。同时还观察到氟原子对反应活性和选择性的显著影响。

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