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Radical amination with trimethylstannylated benzophenone imine
Marie-Céline Lamas1, Santiago E Vaillard, Birgit Wibbeling
1Organisch-Chemisches Institut, Westfälische Wilhelms-Universität, Corrensstrasse 40, 48149 Münster, Germany.
Organic Letters
|April 6, 2010
Summary
This study introduces a novel radical amination method using a benzophenone imine derivative to create imines. These imines are then reduced to valuable secondary amines, expanding synthetic possibilities.
Area of Science:
- Organic Chemistry
- Synthetic Chemistry
Background:
- Radical amination is a crucial transformation for synthesizing nitrogen-containing compounds.
- Developing efficient and versatile methods for radical amination remains an active area of research.
Purpose of the Study:
- To develop a novel intermolecular radical amination reaction.
- To utilize a new radical acceptor for the synthesis of imines.
- To demonstrate the utility of the synthesized imines in further transformations.
Main Methods:
- Intermolecular radical amination of primary, secondary, and tertiary alkyl radicals.
- Use of trimethylstannylated benzophenone imine as a radical acceptor.
- Reduction of the resulting imines using sodium borohydride (NaBH(4)).
Main Results:
- Successful synthesis of various imines (type B) from alkyl radicals.
- Efficient reduction of imines to corresponding secondary amines (type C).
- Demonstration of the compatibility of this radical amination with radical cyclization reactions.
Conclusions:
- A novel and effective method for intermolecular radical amination has been established.
- The developed protocol provides access to valuable secondary amine building blocks.
- The reaction offers a versatile platform for complex molecule synthesis through combination with cyclization strategies.
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