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

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

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

Fu-Min Liao et al. Angew Chem Int Ed Engl. .

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 AuI catalysis plays a key role in this reaction. Remarkable fluorine effects on the reactivity and selectivity was also observed.

Keywords: coupling reactions; diazo reagents; fluorine effects; gold catalysis; olefination.

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