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Strong Hydrogen Bond Donating Solvents Accelerate the Passerini Three-Component Reaction.

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Adding hexafluoroisopropanol (HFIP) as a cosolvent significantly enhances Passerini reaction (P-3CR) rates, even with hydrogen bond donating alcohols. This discovery offers a new strategy for optimizing P-3CR reactions.

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Area of Science:

  • Organic Chemistry
  • Reaction Kinetics

Background:

  • The Passerini reaction (P-3CR) is a key multicomponent reaction in organic synthesis.
  • Alcoholic solvents typically hinder P-3CR due to increased energy barriers in the rate-determining step.

Purpose of the Study:

  • To investigate the effect of 1,1,1,3,3,3-hexafluoroisopropanol (HFIP) as a cosolvent on P-3CR rates.
  • To elucidate the mechanistic basis for observed rate enhancements.

Main Methods:

  • Experimental kinetic studies.
  • Density Functional Theory (DFT) calculations.
  • Substrate scope investigation.

Main Results:

  • Significant rate enhancements were observed for the P-3CR when using HFIP as a cosolvent across most aprotic organic solvents.
  • Rate enhancements were generally observed even with strong hydrogen bond donating (HBD) alcohols.
  • Strong hydrogen bond accepting (HBA) solvents like DMF did not show rate enhancement.
  • The substrate scope revealed a slight increase in overall yield for the P-3CR.

Conclusions:

  • HFIP acts as an effective cosolvent to accelerate the P-3CR, contrary to the typical effect of alcohols.
  • The mechanistic rationale involves specific interactions that lower the activation energy of the rate-determining step.
  • This finding provides a valuable method for optimizing P-3CR reaction efficiency.