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Iodine/ tert ‐Butyl Hydroperoxide‐Mediated Reaction of Indoles with Dimethylformamide/Dimethylacetamide to Synthesize Bis‐ and Tris(indolyl)methanes
Author(s) -
Deb Mohit L.,
Borpatra Paran J.,
Pegu Choitanya Dev,
Thakuria Ranjit,
Saikia Prakash J.,
Baruah Pranjal K.
Publication year - 2017
Publication title -
chemistryselect
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.437
H-Index - 34
ISSN - 2365-6549
DOI - 10.1002/slct.201601857
Subject(s) - dimethylacetamide , chemistry , dimethylformamide , catalysis , iodine , methylene , tris , decane , iodine monochloride , metal , organic chemistry , medicinal chemistry , solvent , biochemistry
Here we report a metal‐free iodine/ tert ‐butyl hydroperoxide mediated reaction of N‐substituted indoles with dimethylformamide (DMF) / dimethylacetamide (DMA). The reaction produces bis‐ and tris(indolyl)methanes (BIMs and TIMs), in which DMF/DMA provides the methylene (of BIMs) and methine carbons (of TIMs). We have established different optimized conditions for their synthesis. Iodine (10 mol %) with TBHP (in decane, 1.0 equivalent) in DMF/DMA at 130 °C is required for the BIMs synthesis, whereas iodine (20 mol %) with TBHP (in water, 3.0 equivalent) in DMF‐H 2 O or DMA‐H 2 O (9:1) is needed for the TIMs. This methodology could be used to synthesize a variety of BIMs and TIMs. We believe, this is the first report of their metal‐free synthesis through C−H functionalization using one carbon source. The use of inexpensive, metal‐free and environmentally benign catalyst made the method handy.