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05:21
A Scalable Balz-Schiemann Reaction Protocol in a Continuous Flow Reactor
Published on: February 10, 2023
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An efficient continuous flow approach to furnish furan-based biaryls
Trieu N Trinh1, Lacey Hizartzidis, Andrew J S Lin
1Chemistry, Centre for Chemical Biology, The University of Newcastle, University Drive, Callaghan, NSW 2308, Australia. Adam.McCluskey@newcastle.edu.au.
Organic & Biomolecular Chemistry
|October 22, 2014
Summary
Continuous flow Suzuki cross-couplings were optimized using immobilized palladium catalysts. These methods efficiently synthesize aryl bromides and chlorides, including the Hedgehog pathway inhibitor LDE225.
Area of Science:
- Organic Chemistry
- Catalysis
- Flow Chemistry
Background:
- Suzuki cross-coupling is a vital reaction in organic synthesis.
- Developing efficient and versatile catalytic systems remains a key challenge.
Purpose of the Study:
- To optimize continuous flow Suzuki cross-coupling reactions.
- To develop versatile methods for coupling various aryl halides with 5-formyl-2-furanylboronic acid.
Main Methods:
- Utilized immobilized palladium catalysts (CatCart™ FC1032™ and CatCart™ PdCl2(PPh3)2-DVB) in continuous flow systems.
- Employed tetrabutylammonium fluoride ((Bu)4N(+)F(-)) and tetrabutylammonium acetate ((Bu)4N(+)OAc(-)) as additives.
- Investigated couplings with activated, neutral, and deactivated aryl bromides, as well as activated aryl chlorides.
Main Results:
- Successfully performed Suzuki couplings of 5-formyl-2-furanylboronic acid with activated/neutral aryl bromides using CatCart™ FC1032™ and (Bu)4N(+)F(-).
- Achieved cross-coupling of deactivated aryl bromides and activated aryl chlorides using CatCart™ PdCl2(PPh3)2-DVB and (Bu)4N(+)OAc(-).
- Demonstrated the protocol's applicability in synthesizing the Hedgehog pathway inhibitor LDE225.
Conclusions:
- Developed efficient continuous flow Suzuki cross-coupling protocols using immobilized palladium catalysts.
- The bis-triphenylphosphine catalyst system shows potential as a universal approach for Suzuki couplings.
- These flow chemistry methods offer a practical route for synthesizing complex molecules, including pharmaceutical intermediates.
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