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.
Abstract:
Silicon-based cross-coupling has been recognized as one of the most reliable alternatives for constructing carbon-carbon bonds. However, the employment of such reaction as an efficient ring expansion strategy for silacycle synthesis is comparatively little known. Herein, we develop the first intermolecular silacyclization strategy involving Pd-catalyzed silicon-based C(sp2)-C(sp3) cross-coupling. This method allows the modular assembly of a vast array of structurally novel and interesting sila-benzo[b]oxepines with good functional group tolerance. The key to success for this reaction is that silicon atoms have a stronger affinity for oxygen nucleophiles than carbon nucleophiles, and silacyclobutanes (SCBs) have inherent ring-strain-release Lewis acidity.
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