Get access

Highly Efficient Povidone–Phosphotungstic Acid Catalyst for the Tandem Acetalization of Aldehydes to Bis- and Tris(indolyl)methanes

Authors

  • Sumit B. Kamble,

    1. Chemical Engineering and Process Development Division, CSIR-National Chemical Laboratory, Dr. Homi Bhabha Road, Pune 411008 (India), Fax: (+91) 2590-2620
    Search for more papers by this author
  • Rameshwar K. Swami,

    1. Chemical Engineering and Process Development Division, CSIR-National Chemical Laboratory, Dr. Homi Bhabha Road, Pune 411008 (India), Fax: (+91) 2590-2620
    Search for more papers by this author
  • Sachin S. Sakate,

    1. Chemical Engineering and Process Development Division, CSIR-National Chemical Laboratory, Dr. Homi Bhabha Road, Pune 411008 (India), Fax: (+91) 2590-2620
    Search for more papers by this author
  • Dr. Chandrashekhar V. Rode

    Corresponding author
    1. Chemical Engineering and Process Development Division, CSIR-National Chemical Laboratory, Dr. Homi Bhabha Road, Pune 411008 (India), Fax: (+91) 2590-2620
    • Chemical Engineering and Process Development Division, CSIR-National Chemical Laboratory, Dr. Homi Bhabha Road, Pune 411008 (India), Fax: (+91) 2590-2620

    Search for more papers by this author

Abstract

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 31P 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.

Ancillary