Understanding the efficacy of N,N-dimethylformamide and oxalyl chloride combination as chemoselective O-formylating agent: An unified experimental and theoretical study |
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| Authors: | Shaikh Batuta Md Ashif Ali Anirban Chatterjee Md Niharul Alam Sreeparna Das Debabrata Mandal |
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| Institution: | 1. Department of Chemistry, Visva-Bharati (Central University), Santiniketan, West Bengal, India;2. Department of Chemistry, University College of Science and Technology, University of Calcutta, Kolkata, India |
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| Abstract: | We have developed a simple but efficient synthetic protocol for the O-formylation of a wide range of aromatic hydroxyl/phenolic substrates using an N,N-dimethylformamide (DMF) and oxalyl chloride (COCl)2] combination in dichloromethane (DCM) as solvent at ambient temperature. The DMF/(COCl)2 combination was found to be highly chemoselective for the aromatic/phenolic hydroxyl group over aliphatic hydroxyl or aromatic amine/thiol groups. This chemoselectivity of DMF/(COCl)2 combination towards O-formylation of aromatic alcohols was explained on the basis of outcomes of both experimental and density functional theory–based theoretical studies. |
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| Keywords: | Aromatic alcohols chemoselective O-formylation N N-dimethylformamide oxalyl chloride |
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