Silacyclization through palladium-catalyzed intermolecular silicon-based C(sp2)-C(sp3) cross-coupling
Ying Qin1, Lianghui Li1, Jin-Yuan Liang1
1State Key Laboratory and Institute of Elemento-Organic Chemistry, Frontiers Science Center for New Organic Matter, College of Chemistry, Nankai University Tianjin 300071 China dongbing.chem@nankai.edu.cn.
This study introduces a novel palladium-catalyzed silicon-based cross-coupling reaction for synthesizing sila-benzo[b]oxepines. This efficient ring expansion strategy offers a new route for creating complex silicon-containing heterocyclic compounds.
Area of Science:
- Organosilicon Chemistry
- Synthetic Organic Chemistry
- Catalysis
Background:
- Silicon-based cross-coupling is a reliable method for C-C bond formation.
- Its application in silacycle synthesis via ring expansion is underexplored.
Purpose of the Study:
- To develop the first intermolecular silacyclization strategy for ring expansion.
- To synthesize novel sila-benzo[b]oxepines using palladium catalysis.
Main Methods:
- Employing palladium-catalyzed silicon-based C(sp2)-C(sp3) cross-coupling.
- Utilizing silacyclobutanes (SCBs) as key building blocks.
Main Results:
- Successfully developed an efficient intermolecular silacyclization strategy.
- Modularly assembled diverse and novel sila-benzo[b]oxepines.
- Demonstrated good functional group tolerance in the reaction.
Conclusions:
- The developed method provides a new avenue for silacycle synthesis.
- The reaction's success is attributed to silicon's affinity for oxygen and SCB ring strain.
- Offers a versatile approach for constructing complex organosilicon heterocycles.
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