4.8 Article

Double Arylation of Allyl Alcohol via a One-Pot Heck Arylation-Isomerization-Acylation Cascade

Journal

ORGANIC LETTERS
Volume 13, Issue 20, Pages 5456-5459

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/ol202144z

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Funding

  1. EPSRC [EP/F000316]
  2. AstraZeneca
  3. EPSRC [EP/F000316/1] Funding Source: UKRI
  4. Engineering and Physical Sciences Research Council [EP/F000316/1] Funding Source: researchfish

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A one-pot, two-step catalytic protocol has been developed. A regloselective Heck coupling between aryl bromides and allyl alcohol leads to the generation of arylated allyl alcohols that in situ isomerize to give aldehydes, which then undergo an acylation reaction with a second aryl bromide. A variety of aryl bromides can be employed in both the initial Heck reaction and the acylation, providing easy access to a wide variety of substituted dihydrochalcones.

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