A Non-Cross-Linked Soluble Polystyrene-Supported Ruthenium Catalyst for Carbenoid Transfer Reactions

• Published in: Chemistry, an Asian journal an Asian journal, 2008-09, Vol.3 (8-9), p.1256-1265
• Main Authors: Choi, Matthew Kwok-Wai, Yu, Wing-Yiu, So, Man-Ho, Zhou, Cong-Ying, Deng, Qing-Hai, Che, Chi-Ming
• Format: Article
• Language: English
• Subjects: Alkenes - chemistry; carbenoid; Catalysis; Cross-Linking Reagents - chemistry; Cyclopropanes - chemistry; Metal Nanoparticles - chemistry; Metal Nanoparticles - ultrastructure; Methane - analogs & derivatives; Methane - chemistry; Microscopy, Electron, Transmission; Molecular Structure; nanoparticles; Polystyrenes - chemistry; ruthenium; Ruthenium - chemistry; Solubility; soluble polymers; Spectrum Analysis
• ISSN: 1861-4728; 1861-471X
• DOI: 10.1002/asia.200800144

Ruthenium nanoparticles supported on non‐cross‐linked soluble polystyrene were prepared by reacting [RuCl2(C6H5CO2Et)]2 with polystyrene in open air. They effectively catalyze intra‐ and intermolecular carbenoid insertion into CH and NH bonds, alkene cyclopropanation, and ammonium ylide/[2,3]‐sigmatropic rearrangement reactions. This supported ruthenium catalyst is much more reactive than [RuCl2(p‐cymene)]2 and [Ru(Por)CO] for catalytic intermolecular carbenoid CH bond insertion into saturated alkanes. By using α‐diazoacetamide as a substrate for intramolecular carbenoid CH insertion, the supported ruthenium catalyst can be recovered and reused for ten successive iterations without significant loss of activity. Ruthenium catalyst for versatile carbenoid transfer reactions! Reusable, soluble polymer‐supported ruthenium nanoparticles were employed as catalysts for a variety of carbenoid transfer reactions (intra‐ and intermolecular carbenoid insertion to CH and NH bonds, alkene cyclopropanation, and ammonium ylide/[2,3]‐sigmatropic rearrangement reactions) with high substrate conversion and product turnover.