Skip to Main content Skip to Navigation
New interface
Theses

Evolution of diamination : from intra- to intermolecular version

Abstract : We have first been interested in the 1,2-intermolecular diamination of allylic ethers and managed to develop a first version. This reaction employs catalytic amounts of palladium(II) compounds as catalyst source and proceeds with complete regio- and stereoselectivity. It represents a significant advance in oxidative 1,2-difunctionalization of alkenes. Then we have realized an optimization and simplification of the procedure allowing the diamination of allylic ethers through the use of only one equivalent of alkene and one oxidant. The reaction employs catalytic amounts of palladium(II) compounds as catalyst source and proceeds again with complete regioselectivity in mild conditions compatible with a large number of chemical functions. The scope of the reaction has been enlarged to aliphatic alkenes with moderate to good yields using the more acidic nitrogen source tetrafluorophthalimide. Finally, we have been interested in, and then realized, the first general intermolecular 1,4-diamination of dienes. The reaction employs economic reagents such as CuBr2 and saccharin and proceeds with complete regioselectivity under mild conditions. It represents this time a significant advance in oxidative 1,4-difunctionalization of dienes. Work in order to understand the underlying mechanisms as well as to develop further these reactions is ongoing.
Document type :
Theses
Complete list of metadata

Cited literature [93 references]  Display  Hide  Download

https://tel.archives-ouvertes.fr/tel-00856587
Contributor : ABES STAR :  Contact
Submitted on : Monday, September 2, 2013 - 1:12:54 AM
Last modification on : Friday, August 5, 2022 - 9:27:47 AM

File

KIRSCH_Jonathan_2012_ED222.pdf
Version validated by the jury (STAR)

Identifiers

  • HAL Id : tel-00856587, version 1

Collections

Citation

Jonathan Kirsch. Evolution of diamination : from intra- to intermolecular version. Other. Université de Strasbourg, 2012. English. ⟨NNT : 2012STRAF038⟩. ⟨tel-00856587⟩

Share

Metrics

Record views

143

Files downloads

727