4.8 Article

Zinc-Catalyzed Dehydrogenative Cross-Coupling of Terminal Alkynes with Aldehydes: Access to Ynones

Journal

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 54, Issue 52, Pages 15850-15853

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201509042

Keywords

C-H activation; cross-coupling; dehydrogenation; homogeneous catalysis; zinc

Funding

  1. 973 Program [2012CB725302]
  2. National Natural Science Foundation of China [21390400, 21520102003, 21272180, 21302148]
  3. Hubei Province Natural Science Foundation of China [2013CFA081]
  4. Research Fund for the Doctoral Program of Higher Education of China [20120141130002]
  5. Ministry of Science and Technology of China [2012YQ120060]
  6. Program of Introducing Talents of Discipline to Universities of China (111 Program)

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Because of the lack of redox ability, zinc has seldom been used as a catalyst in dehydrogenative cross-coupling reactions. Herein, a novel zinc-catalyzed dehydrogenative C(sp(2))-H/C(sp)-H cross-coupling of terminal alkynes with aldehydes was developed, and provides a simple way to access ynones from readily available materials under mild reaction conditions. Good reaction selectivity can be achieved with a 1: 1 ratio of terminal alkyne and aldehyde. Various terminal alkynes and aldehydes are suitable in this transformation.

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