4.5 Article

Transition-Metal-Free Oxidative Cross-Coupling of Methylhetarenes with Imidazoheterocycles towards Efficient C(sp2)-H Carbonylation

Journal

ASIAN JOURNAL OF ORGANIC CHEMISTRY
Volume 6, Issue 7, Pages 890-897

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/ajoc.201700173

Keywords

carbonylation; cross-coupling; green chemistry; heterocycles; oxidation

Funding

  1. Council of Scientific and Industrial Research (CSIR), New Delhi under the 12th five-year plan (FYP) project Affordable Cancer Therapeutics (ACT) [CSC0301]
  2. Science and Engineering Research Board (SERB), New Delhi under Start-up Grant for Young Scientists Scheme [SB/FT/CS-071/2014]
  3. International Scientific Partnership Program (ISPP) at King Saud University [ISPP0054]
  4. Commission (UGC)
  5. CSIR

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An efficient method for the oxidative cross-coupling of methylhetarenes with imidazoheterocycles by employing an eco-friendly iodine/DMSO reagent system has been developed. This C(sp(2))-H carbonylation reaction proceeds through an in situ oxidation of a methylhetarene into a formylhetarene followed by an oxidative cross-coupling reaction with an imidazoheterocycle. This method has a wide substrate scope and good functional group tolerance and enables the construction of a large number of carbonylated imidazoheterocycles in very good yields.

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