Ligand-Enabled β-C(sp3)-H Olefination of Free Carboxylic Acids.

An acetyl-protected aminoethyl phenyl thioether has been developed to promote C(sp3)-H activation. Significant ligand enhancement is demonstrated by the realization of the first Pd(II)-catalyzed olefination of C(sp3)-H bonds of free carboxylic acids without using an auxiliary. Subsequent lactonization of the olefinated product via 1,4 addition provided exclusively monoselectivity in the presence of multiple β-C-H bonds. The product γ-lactone can be readily opened to give either the highly valuable β-olefinated or γ-hydroxylated aliphatic acids. Considering the challenges in developing Heck couplings using alkyl halides, this reaction offers a useful alternative.

• Publication year

  2018

• Venue

  Journal of the American Chemical Society

• Publication date

  2018-07-20

• Fields of study

  Medicine, Chemistry

• Identifiers
  DOI 10.1021/jacs.8b06527PMID 30029574PMCID PMC6524951
• External record

  Open on Semantic Scholar

• Source metadata

  Semantic Scholar, PubMed

• No claims are published for this paper.

• No concepts are published for this paper.

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