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Published on: May 21, 2019
Aroylation of Electron-Rich Pyrroles under Minisci Reaction Conditions
Joydev K Laha1, Mandeep Kaur Hunjan1, Shalakha Hegde1
1Department of Pharmaceutical Technology (Process Chemistry) , National Institute of Pharmaceutical Education and Research , S. A. S. Nagar , Punjab 160062 , India.
Abstract:
The development of Minisci acylation on electron-rich pyrroles under silver-free neutral conditions has been reported featuring the regioselective monoacylation of (NH)-free pyrroles. Unlike conventional Minisci conditions, the avoidance of any acid that could result in the polymerization of pyrroles was the key to success. The umpolung reactivity of the nucleophilic acyl radical, generated in situ from arylglyoxylic acid, could help explain the mechanism of product formation with electron-rich pyrroles. Alternatively, the nucleophilic substitution of the acyl radical on the electron-deficient pyrrole radical cation is proposed.
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