AuCl₃ -Catalyzed Ring-Closing Carbonyl-Olefin Metathesis

Area of Science:

• Organic Chemistry
• Catalysis

Background:

• Olefin metathesis is a mature field, but carbonyl-olefin metathesis for C=C bond formation is underdeveloped.
• Catalytic methods for carbonyl-olefin metathesis are scarce, limiting its application.

Purpose of the Study:

• To develop an efficient catalytic method for intramolecular ring-closing carbonyl-olefin metathesis.
• To expand the synthetic utility of carbonyl-olefin metathesis for constructing cyclic organic molecules.

Main Methods:

• Utilized a gold(III) chloride (AuCl3) catalyst for the intramolecular ring-closing carbonyl-olefin metathesis reaction.
• Employed easily accessible starting materials and straightforward reaction conditions.

Main Results:

• Achieved good to excellent yields of target compounds.
• Successfully synthesized cyclopentenes, polycycles, benzocarbocycles, and N-heterocycle derivatives.
• Demonstrated good functional group tolerance and short reaction times.

Conclusions:

• The developed AuCl3-catalyzed method provides an efficient route for carbonyl-olefin metathesis.
• This reaction expands the toolbox for synthesizing diverse cyclic structures, including valuable heterocyclic compounds.