Yb(OTf)₃-Catalyzed and Di-tert-butyl Dicarbonate-Mediated Decarboxylative Etherification and Esterification Reactions

Area of Science:

• Organic Chemistry
• Catalysis
• Synthetic Methodology

Background:

• Protecting group chemistry is crucial in organic synthesis.
• Ytterbium triflate (Yb(OTf)3) is known for catalytic deprotection, not protection reactions.
• Tert-butyl ethers are common protecting groups for alcohols.

Purpose of the Study:

• To explore the use of Yb(OTf)3 as a catalyst for alcohol protection.
• To develop an efficient protocol for forming tert-butyl ethers using Yb(OTf)3.
• To investigate the applicability of this method for protecting carboxylic acids.

Main Methods:

• Catalytic reaction of alcohols with di-tert-butyl dicarbonate (Boc2O).
• Screening of reaction conditions including solvent, temperature, and time.
• Optimization of the Yb(OTf)3-catalyzed etherification process.

Main Results:

• Yb(OTf)3 effectively catalyzes the formation of tert-butyl ethers from alcohols.
• Achieved up to 92% conversion within one hour, significantly reducing reaction time.
• Demonstrated successful application for the protection of carboxylic acids.

Conclusions:

• Yb(OTf)3 is a novel and efficient catalyst for tert-butyl ether formation.
• The developed protocol offers a faster and effective method for alcohol protection.
• This methodology expands the utility of Yb(OTf)3 in synthetic organic chemistry.