HFIP-Mediated Deoxygenative Dual C-Arylation Process for the Generation of Quaternary C(sp3)-Center: Synthesis of
Yaqoob A Teli1, Mayur Jagdishbhai Patel2, Abhishek Panwar1
1Department of Chemistry, National Institute of Technology Manipur, Langol, Imphal, Manipur, 795004, India.
Abstract:
A deoxygenative dual C-arylation strategy has been described toward the synthesis of 3,3-diaryloxyindoles. The developed method is accomplished under sonochemical and thermal conditions using HFIP as a recyclable reagent. This strategy features the generation of quaternary C(sp3)-center using readily available bis-diones to generate the desired molecules in excellent yields (up to 96%). Using this method, the biologically active molecules such as trisindoline, which is known to exhibit stronger toxicity against both multidrug-resistant cell lines HCT15/CL02 and MES-SA/DX5, and oxyphenisatin molecules, which are known to be potent antiproliferative agents against cell lines MDA-468 are synthesized. The developed reaction method can be easily employed in a gram-scale synthesis, and the recyclability and reusability of HFIP have been tested. A plausible reaction mechanism is proposed, which is well supported by control experiments, GC-MS analysis, and DFT studies.
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