Recyclable 2nd generation ionic liquids as green solvents for the oxidation of alcohols with hypervalent iodine reagents
J. S. Yadav*, B. V. S. Reddy, A. K. Basak and A. Venkat Narsaiah
*Division of Organic Chemistry, Indian Institute of Chemical Technology,
Hyderabad 500007, India, Email: yadavpub
iict.res.in
J. S. Yadav, B. V. S. Reddy, A. K. Basak, A. V. Narsaiah, Tetrahedron, 2004, 60, 2131-2135.
DOI: 10.1016/j.tet.2003.12.056
Abstract
Alcohols are oxidized to the corresponding carbonyl compounds with iodoxybenzoic acid (IBX) or with Dess-Martin-Periodinane (DMP) in [bmim]BF4 and [bmim]PF6 ionic liquids at room temperature in excellent yields with high selectivity. These oxidations are faster in ionic liquids as compared to conventional solvents. The byproduct iodosobenzoic acid (IBA) and the ionic liquid are readily recovered.
see
article for more examples
Details
The study explores the use of recyclable second-generation ionic liquids as green solvents for the oxidation of alcohols using hypervalent iodine reagents, specifically iodoxybenzoic acid (IBX) and Dess–Martin-Periodinane (DMP). Conducted by J. S. Yadav and colleagues at the Indian Institute of Chemical Technology, the research demonstrates that alcohols can be smoothly oxidized to carbonyl compounds in hydrophilic [bmim]BF4 and hydrophobic [bmim]PF6 ionic liquids at room temperature. These reactions are faster and more efficient in ionic liquids compared to conventional solvents like DMSO, DMF, EtOAc, and H2O. The process is environmentally friendly, offering high yields and selectivity, and allows for the easy recovery and recycling of the ionic liquids and byproducts. The study highlights the advantages of using ionic liquids, such as their negligible vapor pressure, high thermal stability, and good solvating ability, which make them ideal for green chemistry applications. The research also shows that IBX and DMP oxidations in ionic liquids avoid the need for high temperatures and long reaction times, making the process more convenient and eco-friendly. The findings suggest that ionic liquids can be a viable alternative to traditional solvents in oxidation reactions.
Key Words
Dess-Martin Oxidation, Dess-Martin Periodinane (DMP), Iodoxybenzoic acid (IBX), Ionic Liquids
ID: J72-Y2004-250
