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

Journal

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 56, Issue 9, Pages 2459-2463

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201611625

Keywords

coupling reactions; diazo reagents; fluorine effects; gold catalysis; olefination

Funding

  1. 973 program [2015CB856600]
  2. NSFC [21472049]
  3. Ministry of Education (PCSIRT)

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

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