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Practical Pd(II)-Catalyzed C–H Alkylation with Epoxides: One-Step Syntheses of 3,4-Dihydroisocoumarins

Authors
  • Guolin Cheng
  • Tuan-Jie Li
  • Jin-Quan Yu
Type
Published Article
Journal
Journal of the American Chemical Society
Publisher
American Chemical Society
Volume
137
Issue
34
Pages
10950–10953
Identifiers
DOI: 10.1021/jacs.5b07507
Source
CCHF
Keywords
License
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Abstract

Pd(II)-catalyzed ortho-alkylation of benzoic acids with both terminal and internal epoxides affords 3,4-dihydroisocoumarins in one step. The presence of potassium countercations is crucial for this reaction. Monoprotected amino acid ligands significantly promote this reaction, enabling the development of a practical C–H alkylation reaction using 0.5 mol % Pd catalyst. The inversion of stereochemistry in the C–H alkylation step is consistent with a redox-neutral SN2 nucleophilic ring-opening process as opposed to a Pd(II)/Pd(IV) pathway.

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