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Cross-metathesis assisted by microwave irradiation.
Frédéric C Bargiggia1, William V Murray
1Johnson & Johnson Pharmaceutical Research and Development L.L.C., 1000 Route 202, P.O. Box 300, Raritan, New Jersey 08869, USA.
The Journal of Organic Chemistry
|November 5, 2005
Summary
Microwave irradiation significantly speeds up cross-coupling metathesis reactions involving deactivated olefins. This acceleration is attributed to efficient heating and increased pressure within the microwave apparatus, not a "microwave effect".
Area of Science:
- Organic Chemistry
- Catalysis
- Green Chemistry
Background:
- Cross-coupling metathesis reactions are crucial in organic synthesis.
- Deactivated olefins present challenges in these reactions.
- Microwave irradiation has been explored for accelerating chemical transformations.
Purpose of the Study:
- To investigate the effect of microwave irradiation on cross-coupling metathesis reactions.
- To evaluate the performance of specific catalysts under microwave conditions.
- To elucidate the mechanism behind observed accelerations.
Main Methods:
- Utilizing microwave irradiation for cross-coupling metathesis.
- Employing phosphine-free Hoveyda-Grubbs catalyst and second-generation Grubbs' catalyst.
- Analyzing reaction kinetics and product yields.
Main Results:
- Significant acceleration of cross-coupling metathesis reactions with deactivated olefins.
- Successful application of both Hoveyda-Grubbs and second-generation Grubbs' catalysts.
- Demonstration that acceleration is due to efficient heating and pressure, not a unique "microwave effect".
Conclusions:
- Microwave irradiation is an effective method for accelerating challenging cross-coupling metathesis reactions.
- The study clarifies the physical basis for microwave-assisted acceleration in these systems.
- This approach offers potential for more efficient synthesis of complex organic molecules.