Non-Diazo C-H Insertion Approach to Cyclobutanones through Oxidative Gold Catalysis.
Zhitong Zheng1, Youliang Wang1,2, Xu Ma1
1Department of Chemistry and Biochemistry, University of California, Santa Barbara, CA, 93106, USA.
We developed an easy method for making cyclobutanones using gold carbenes. This approach simplifies the synthesis of these versatile compounds, offering new possibilities in organic chemistry.
Area of Science:
- Organic Chemistry
- Catalysis
Background:
- Cyclobutanones are valuable synthetic building blocks.
- Traditional synthesis methods for cyclobutanones can be complex and labor-intensive.
Purpose of the Study:
- To report a facile synthesis of cyclobutanones.
- To explore the utility of gold-catalyzed C(sp3)-H insertion chemistry.
Main Methods:
- Utilizing oxidatively generated gold carbenes.
- Employing C(sp3)-H insertion reactions of alkynones.
Main Results:
- Achieved facile synthesis of various cyclobutanones.
- Obtained products in synthetically useful yields.
- Demonstrated the reaction with substrates requiring minimal prefunctionalization.
Conclusions:
- This method provides a straightforward route to cyclobutanones.
- Highlights the synthetic potential of gold-catalyzed oxidative transformations.
- Expands the synthetic utility of alkynones in gold catalysis.
More Related Videos
07:12Cercosporin-Photocatalyzed [4+1]- and [4+2]-Annulations of Azoalkenes Under Mild Conditions
Published on: July 17, 2020
06:34Synthesis of Antiviral Tetrahydrocarbazole Derivatives by Photochemical and Acid-catalyzed C-H Functionalization via Intermediate Peroxides CHIPS
Published on: June 20, 2014
Related Concept Videos
Cycloaddition Reactions: Overview
Cyclohexenones via Michael Addition and Aldol Condensation: The Robinson Annulation
[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction
Cycloaddition Reactions: MO Requirements for Thermal Activation
Cycloaddition Reactions: MO Requirements for Photochemical Activation
Diels–Alder Reaction Forming Cyclic Products: Stereochemistry
