A Simple Method to Create Diarylmethylamides and Carbamates
Author Information
Author(s): Le Gall Erwan, Pignon Antoine, Martens Thierry, Müller Thomas J J
Primary Institution: Institut de Chimie et des Matériaux Paris-Est, UMR 7182 CNRS - Université Paris-Est Créteil
Hypothesis
Can we develop a practical method to synthesize tertiary diarylmethylamides and -carbamates using imines and organozinc reagents?
Conclusion
The study successfully demonstrates a straightforward method for synthesizing diarylmethylamides and -carbamates using a one-pot process.
Supporting Evidence
- The method allows for the use of imines without isolation, simplifying the process.
- Yields of diarylmethylamides and -carbamates ranged from low to high depending on the starting materials.
- Using organozinc reagents is more cost-effective and produces less toxic waste compared to other nucleophiles.
Takeaway
This study shows a new way to make certain chemical compounds quickly and easily using simple ingredients.
Methodology
The method involves forming an imine, activating it with an acyl chloride or chloroformate, and trapping the resulting acyliminium ion with an arylzinc reagent.
Limitations
The harsh conditions required for deprotection of the amide or carbamate function may pose challenges.
Digital Object Identifier (DOI)
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