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Highly Efficient Povidone–Phosphotungstic Acid Catalyst for the Tandem Acetalization of Aldehydes to Bis‐ and Tris(indolyl)methanes
Author(s) -
Kamble Sumit B.,
Swami Rameshwar K.,
Sakate Sachin S.,
Rode Chandrashekhar V.
Publication year - 2013
Publication title -
chempluschem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.801
H-Index - 61
ISSN - 2192-6506
DOI - 10.1002/cplu.201300248
Subject(s) - chemistry , catalysis , indole test , alkylation , phosphotungstic acid , pyridine , methanol , tandem , tris , organic chemistry , friedel–crafts reaction , medicinal chemistry , biochemistry , materials science , composite material
A novel, nonleachable hybrid of heteropoly acid and polyvinylpyrrolidone (or povidone) catalyzes the acetalization of aldehydes in methanol at room temperature followed by reaction with indole to give bis(indolyl)methanes (BIMs) and tris(indolyl)methanes (TIMs) in quantitative yields (90–97 %). The catalyst was shown by pyridine FTIR spectroscopy to possess Brønsted acidity, and the hybrid formation was confirmed by XRD and 31 P NMR studies. Friedel–Crafts alkylation of indole as well as the tandem synthesis of BIMs and TIMs were established with several types of carbonyl and indole substrates to give the corresponding products quantitatively. The catalyst was recycled efficiently for three successive runs without losing its original activity.