Issue 2, 2010
From the journal:

Dalton Transactions

Reactivity and kinetic–mechanistic studies of regioselective reactions of rhodium porphyrins with unactivated olefins in water that form β-hydroxyalkyl complexes and conversion to ketones and epoxides†

Jiadi Zhang,a   Bradford B. Wayland,b   Lin Yun,a   Shan Lib  and  Xuefeng Fu*a  

* Corresponding authors

a Beijing National Laboratory for Molecular Sciences, State Key Lab of Rare Earth Materials Chemistry and Applications, Peking University, Beijing, China
E-mail: fuxf@pku.edu.cn
Fax: +86 10 6275 1708
Tel: +86 10 6275 6035

b Department of Chemistry, Temple University, Philadelphia, PA, USA
E-mail: BWayland@Temple.edu
Fax: +1 215 204 1532
Tel: +1 215 204 7875

Abstract

This article reports on the selective oxidation of unactivated alkenes to ketones and epoxides through the intermediacy of β-hydroxyalkyl rhodium porphyrin complexes which are formed by reactions of terminal alkenes with tetra(p-sulfonatophenyl)porphyrin rhodium(III) complex. The β-hydroxyalkyl rhodium porphyrin complexes in water undergo β-C–H elimination to produce ketones in aqueous pH 9.0 solutions and O–H deprotonation in KOH/DMSO solutions resulting in the rapid and quantitative intramolecular nucleophilic displacement to form 1,2-epoxyalkanes.

Graphical abstract: Reactivity and kinetic–mechanistic studies of regioselective reactions of rhodium porphyrins with unactivated olefins in water that form β-hydroxyalkyl complexes and conversion to ketones and epoxides

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Article information

DOI
https://doi.org/10.1039/B912219B
Article type
Paper
Submitted
22 Jun 2009
Accepted
19 Sep 2009
First published
22 Oct 2009

Dalton Trans., 2010,39, 477-483

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Reactivity and kinetic–mechanistic studies of regioselective reactions of rhodium porphyrins with unactivated olefins in water that form β-hydroxyalkyl complexes and conversion to ketones and epoxides

J. Zhang, B. B. Wayland, L. Yun, S. Li and X. Fu, Dalton Trans., 2010, 39, 477 DOI: 10.1039/B912219B

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