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Regioselective Synthesis of Phenols and Halophenols from Arylboronic Acids Using Solid Poly( N ‐vinylpyrrolidone)/ Hydrogen Peroxide and Poly(4‐vinylpyridine)/Hydrogen Peroxide Complexes
Author(s) -
Prakash G. K. Surya,
Chacko Sujith,
Panja Chiradeep,
Thomas Tisa Elizabeth,
Gurung Laxman,
Rasul Golam,
Mathew Thomas,
Olah George A.
Publication year - 2009
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.200900071
Subject(s) - hydrogen peroxide , chemistry , reagent , n vinylpyrrolidone , phenols , aqueous solution , hydroxylation , regioselectivity , polymer chemistry , peroxide , organic chemistry , polymer , combinatorial chemistry , catalysis , copolymer , enzyme
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.