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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 46, 2016 - Issue 8
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Original Articles

Understanding the efficacy of N,N-dimethylformamide and oxalyl chloride combination as chemoselective O-formylating agent: An unified experimental and theoretical study

Shaikh BatutaDepartment of Chemistry, Visva-Bharati (Central University), Santiniketan, West Bengal, India
,
Md. Ashif AliDepartment of Chemistry, Visva-Bharati (Central University), Santiniketan, West Bengal, India
,
Anirban ChatterjeeDepartment of Chemistry, Visva-Bharati (Central University), Santiniketan, West Bengal, India
,
Md. Niharul AlamDepartment of Chemistry, Visva-Bharati (Central University), Santiniketan, West Bengal, India
,
Sreeparna DasDepartment of Chemistry, Visva-Bharati (Central University), Santiniketan, West Bengal, India
,
Debabrata MandalDepartment of Chemistry, University College of Science and Technology, University of Calcutta, Kolkata, India
&
Naznin Ara BegumDepartment of Chemistry, Visva-Bharati (Central University), Santiniketan, West Bengal, IndiaCorrespondence[email protected]
 show all
Pages 692-700 | Received 24 Nov 2015, Published online: 05 May 2016
 
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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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