Gold-Catalyzed Alkyne Multifunctionalization through an Oxidation-Oxyalkylation-Aryloxylation Sequence

Area of Science:

• Organic Chemistry
• Catalysis
• Synthetic Methodology

Background:

• Terminal alkynes are versatile building blocks in organic synthesis.
• Developing efficient methods for alkyne functionalization remains a key challenge.
• Oxidative coupling reactions offer pathways to complex molecular architectures.

Purpose of the Study:

• To develop a novel gold-catalyzed three-component reaction for alpha-ketoacetal synthesis.
• To establish an efficient one-pot method for the polyfunctionalization of terminal alkynes.
• To explore the use of quinone monoimines in gold-catalyzed transformations.

Main Methods:

• Gold-catalyzed oxidative three-component reaction.
• Utilized terminal alkynes, alcohols, and quinone monoimines as starting materials.
• Employed quinone monoimines for electrophilic interception of gold enolate intermediates.

Main Results:

• Achieved synthesis of alpha-ketoacetals in good to excellent yields.
• Demonstrated an unprecedented oxidation-oxyalkylation-aryloxylation sequence.
• Successfully installed three oxygen atoms onto the C-C triple bond of terminal alkynes.

Conclusions:

• The developed gold-catalyzed reaction provides an efficient route to alpha-ketoacetals.
• This method offers a novel strategy for the polyfunctionalization of terminal alkynes.
• The reaction showcases the utility of quinone monoimines in gold catalysis for complex molecule synthesis.