Dendritic ruthenium porphyrins: a new class of highly selective catalysts for alkene epoxidation and cyclopropanation

Chemistry : a European Journal
Jun-Long ZhangChi-Ming Che

Abstract

Attachment of Fréchet-type poly(benzyl ether) dendrons [G-n] to carbonylruthenium(II) meso-tetraphenylporphyrin (5) using covalent etheric bonds forms a series of dendritic ruthenium(II) porphyrins 5-[G-n](m) (m=4, n=1, 2; m=8, n=0-2). The attachment was realized by treating the carbonylruthenium(II) complex of 5,10,15,20- tetrakis(4'-hydroxyphenyl)porphyrin or 5,10,15,20-tetrakis(3',5'-dihydroxyphenyl)porphyrin with [G-n]OSO(2)Me in refluxing dry acetone in the presence of potassium carbonate and [18]crown-6. Complexes 5-[G-n](m) were characterized by UV/Vis, IR, and NMR spectroscopy and mass spectrometry. All of the dendritic ruthenium porphyrins are highly selective catalysts for epoxidation of alkenes with 2,6-dichloropyridine N-oxide (Cl(2)pyNO). The chemo- or diastereoselectivity increases with the generation number of the dendron and the number of dendrons attached to 5, and complex 5-[G-2](8) exhibits remarkable selectivity or turnover number in catalyzing the Cl(2)pyNO epoxidation of a variety of alkene substrates including styrene, trans-/cis-stilbene, 2,2-dimethylchromene, cyclooctene, and unsaturated steroids such as cholesteryl esters and estratetraene derivative. The cyclopropanation of styrene and its para-substi...Continue Reading

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Citations

Aug 18, 2005·Journal of the American Chemical Society·Raymond P BriñasSergei A Vinogradov
Mar 24, 2016·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Juan C Barona-CastañoKleber T de Oliveira
Oct 13, 2006·Dalton Transactions : an International Journal of Inorganic Chemistry·Tat-Shing LaiChi-Ming Che
Jun 25, 2005·Chemistry : a European Journal·Estelle BurriKay Severin
Sep 14, 2010·Chemical Communications : Chem Comm·Christian HerreroAlly Aukauloo
Jul 2, 2009·Chemical Communications : Chem Comm·Chi-Ming Che, Jie-Sheng Huang
Aug 27, 2009·The Journal of Organic Chemistry·Daniel C G GötzGerhard Bringmann
Oct 9, 2003·Chemical Reviews·Rita Skoda-Földes, László Kollár
Sep 23, 2009·Chemical Reviews·Wei-Shi Li, Takuzo Aida
Jul 20, 2021·Chemical Science·Gracita M TombocKyoungsuk Jin
Aug 5, 2011·Journal of the American Chemical Society·M Shema-MizrachiN G Lemcoff

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