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Substrate-Induced Cooperative Ionic Catalysis: Difunctionalization of Indole Derivatives Employing Dimethyl Carbonate
Sangita Dattatray Shinde1, Ashik Chhetri1, Sayak Ghosh1
1Department of Medicinal Chemistry, National Institute of Pharmaceutical Education and Research (NIPER) - Ahmedabad, Palaj, Gandhinagar-382355, Gujarat, India.
Abstract:
The global urge to adopt sustainable chemistry has resulted in the development of more environmentally benign strategies (EBS) that use CO2 and CO2-derived chemicals in a step-economic manner. In this context, we investigated a dual C-H methylation and (C═O)-methoxylation of indole derivatives using dimethyl carbonate (DMC) in the presence of catalytic amounts of Cs2CO3. Mechanistic insights include DMF-assisted, DMC-induced cooperative ionic catalysis, which allows DMC to act as both a nucleophilic and an electrophilic precursor, resulting in (C═O)-methoxylation and C-H methylation of N-benzylindolyl ketones.
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