Regioselective Synthesis of Phenols and Halophenols from Arylboronic Acids Using Solid Poly(N-vinylpyrrolidone)/ Hydrogen Peroxide and Poly(4-vinylpyridine)/Hydrogen Peroxide Complexes

Solid hydrogen peroxide complexes based on poly(N‐vinylpyrrolidone) and poly(4‐vinylpyridine) were prepared and used as solid hydroxylating reagents. These solid hydrogen peroxide equivalents are found to be much safer, convenient and efficient reagent systems for the ipso‐hydroxylation of arylboron...

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Bibliographic Details
Published in:Advanced synthesis & catalysis 2009-07, Vol.351 (10), p.1567-1574
Main Authors: Prakash, G. K. Surya, Chacko, Sujith, Panja, Chiradeep, Thomas, Tisa Elizabeth, Gurung, Laxman, Rasul, Golam, Mathew, Thomas, Olah, George A.
Format: Article
Language:English
Subjects:
ab initio calculations
hydrogen peroxide
hydroxylation
phenols
regioselectivity
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Summary:Solid hydrogen peroxide complexes based on poly(N‐vinylpyrrolidone) and poly(4‐vinylpyridine) were prepared and used as solid hydroxylating reagents. These solid hydrogen peroxide equivalents are found to be much safer, convenient and efficient reagent systems for the ipso‐hydroxylation of arylboronic acids to the corresponding phenols in high yields at a faster rate. The versatility of the reagents has been further expanded for the one‐pot synthesis of halophenols. Density functional theory calculations were carried out on hydrogen peroxide complexes of N‐ethylpyrrolidone and 4‐ethylpyridine as models to get a better understanding of structure and behavior of hydrogen peroxide complexes of the polymers poly(N‐vinylpyrrolidone) and poly(4‐vinylpyridine) compared to aqueous hydrogen peroxide.
ISSN:1615-4150
1615-4169
DOI:10.1002/adsc.200900071