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General, Mild, and Selective Method for Desaturation of Aliphatic Amines
Padon Chuentragool1, Marvin Parasram1, Yi Shi1
1Department of Chemistry, University of Illinois at Chicago , 845 West Taylor Street, Chicago, Illinois 60607-7061, United States.
Journal of the American Chemical Society
|February 6, 2018
Summary
A new method efficiently converts simple amines into enamines and allylic amines using palladium-radical chemistry. This scalable process operates under mild, photoinduced conditions without external oxidants or photosensitizers.
Area of Science:
- Organic Chemistry
- Catalysis
- Photochemistry
Background:
- Amine functionalization is crucial in organic synthesis.
- Developing selective and mild methods for amine desaturation remains a challenge.
Purpose of the Study:
- To develop a novel and general protocol for the desaturation of aliphatic amines.
- To achieve efficient synthesis of enamines, allylic, and homoallylic amines.
Main Methods:
- Utilized putative aryl hybrid Pd-radical intermediates.
- Employed a combination of hydrogen atom transfer (HAT) and beta-hydride elimination.
- Operated under mild, photoinduced conditions without exogenous photosensitizers or oxidants.
Main Results:
- Achieved efficient and selective desaturation of various amines.
- Demonstrated tunable selectivity of HAT by varying auxiliaries.
- Showcased the generality of the developed protocol.
- Confirmed scalability of the method from simple amines.
Conclusions:
- The novel Pd-radical protocol offers a mild, efficient, and scalable route to valuable amine derivatives.
- The method's versatility and tunable selectivity make it a significant advancement in amine chemistry.
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