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Facile Preparation of 2Z,4E-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
Published on: June 21, 2017
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Anomeric Amide-Enabled Alkene-Arene and Alkene-Alkene Aminative Coupling
Colin Stein1, Jasper L Tyler1, Julius Wiener1
1Organisch-Chemisches Institut, Universität Münster, Corrensstraße 36, 48149, Münster.
Angewandte Chemie (International Ed. in English)
|November 28, 2024
Summary
This study introduces a novel anomeric amide reagent for efficient aminative coupling reactions. The one-pot, catalyst-free method enables regioselective alkene-arene and alkene-alkene bond formation, expanding synthetic strategies.
Area of Science:
- Organic Chemistry
- Synthetic Methodology
Background:
- Carbon-nitrogen (C-N) bond forming cross-coupling reactions are widely used.
- Aminative coupling, assembling fragments directly at a heteroatom, is an underexplored strategy.
Purpose of the Study:
- To design and synthesize a novel anomeric amide reagent.
- To develop a regioselective aminative coupling protocol for alkene-arene and alkene-alkene reactions.
Main Methods:
- One-pot synthesis involving chloroamination, N-deprotection, and nitrene functionalization.
- Catalyst-free reaction conditions.
- High-throughput experimentation (HTE) for rapid scope exploration.
Main Results:
- Successful implementation of an anomeric amide reagent for aminative coupling.
- Achieved highly regioselective alkene-arene and alkene-alkene coupling.
- Demonstrated divergent reactivity from functionalized intermediates.
Conclusions:
- The developed protocol offers a simple and efficient method for C-N bond formation.
- The anomeric amide reagent expands the scope of aminative coupling strategies.
- The methodology allows for rapid exploration of chemical space and diverse synthetic applications.
Keywords:
Aminative couplingAnomeric amidesChloroaminationMulti-component reactionsNitrenoid transferMore Related Videos
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