4.8 Article

Efficient Synthesis of E-α-Haloenones Through Chemoselective Alkyne Activation Over Allene with Triazole-Au Catalysts

Journal

ORGANIC LETTERS
Volume 12, Issue 9, Pages 2088-2091

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/ol100576m

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Funding

  1. NSF [CHE-0844602]
  2. DOE [DE-FC26-04NT42136]
  3. [ACS-PRF-47843-G1]
  4. Direct For Mathematical & Physical Scien
  5. Division Of Chemistry [0844602] Funding Source: National Science Foundation

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The E-alpha-haloenones were prepared through a triazole-Au complex (TriA-Au) catalyzed propargyl acetate rearrangement and sequential allene halogenation. The reactions proceeded with only 1% catalyst loading, giving the challenging kinetic products in excellent yields and good to excellent stereoselectivity. These results not only provided the first example for the synthesis of challenging kinetic E-haloenones, but also revealed triazole Au complexes as effective catalysts in promoting chemoselective activation of alkynes over allenes.

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