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February 28, 2026Synlett0 citations

Activating Highly Hindered Anhydrides for Use in Masking Alcohols and Polyols – A New Method Inspired by Cationic Palladium

EMEnoch A. MensahJSJasmine Sabet-LeBlancEDElizabeth A. Davis

Key Points

  • To develop a new method for activating highly hindered acid anhydrides using cationic palladium to mask alcohols and polyols.
  • Utilized a cationic palladium catalyst Pd(PhCN)2(OTf)2 generated in situ from Pd(PhCN)2Cl2 and AgTOf.
  • Activated highly hindered acid anhydrides for acylation of alcohols and polyols.
  • Carried out reactions mostly at room temperature with 1 mol% catalyst loading.
  • Achieved good to excellent yields in masking various alcohols and polyols.
  • Demonstrated a broad substrate scope for efficient acylation processes.
  • Showed effectiveness with minimal catalyst usage, enhancing efficiency.

Abstract

A new method inspired by cationic palladium (II) species in activating highly hindered acid anhydrides in masking alcohols and polyols is described. This protocol utilizes a cationic palladium catalyst, Pd(PhCN)2(OTf)2 generated in situ from 1 mol % Pd(PhCN)2Cl2 and 2 mol % AgTOf to activate highly hindered acid anhydrides, and to direct the acylation process. This new method is highly efficient and proceeds with only 1 mol% of the catalyst loading at mostly room temperature. The method has a wide substrate scope in masking different alcohols and polyols with robust protecting groups in good to excellent yields.

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Cite This Study

Mensah et al. (2026) studied this question.

synapsesocial.com/papers/69a287240a974eb0d3c02ac1https://doi.org/10.1055/a-2822-9058
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