4.8 Article

Highly Selective Cascade C-C Bond Formation via Palladium-Catalyzed Oxidative Carbonylation-Carbocyclization-Carbonylation-Alkynylation of Enallenes

Journal

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 137, Issue 37, Pages 11868-11871

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/jacs.5b06828

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Funding

  1. European Research Council [ERC AdG 247014]
  2. Swedish Research Council [621-2013-4653]
  3. Berzelii Center EXSELENT
  4. Knut and Alice Wallenberg Foundation

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A highly efficient palladium-catalyzed oxidative cascade reaction of enallenes undergoing overall four C-C bond formations has been developed. The insertion cascade proceeds via carbonylation carbocyclization carbonylation alkynylation involving sequential insertion of carbon monoxide, olefin, and carbon monoxide. Furthermore, different types of terminal alkynes and functionalized enallenes have been investigated and found to undergo the cascade reaction under mild reaction conditions.

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