Domain, Specialties : Chemistry
Keywords: organic chemistry, photocatalysis
Research Unit : NIMBE / LCMCE
Summary
The internship involves the development of a new synthetic method for forming C-N bonds, called transfer carboamination. This approach uses alkenes and hydroxylamines as substrates. The project aims to optimize the reaction under photocatalytic conditions using iron-based catalysts and to study its scope of application. The trainee will develop skills in photocatalysis, organic and organometallic synthesis, and analytical techniques.
Full description
Central in fine chemistry and estimated to represent 35% of all reactions used in the pharmaceutical industry, the formation of C–N bonds relies on three main strategies: the N-alkylation with alkyl halides, the reductive amination of carbonyl derivatives and the cross-coupling of aryl halides with amines. All of them require, however, the use of either petroleum-based halide derivatives or stoichiometric reducing agents and lead to the production of stoichiometric waste, hence the need to develop new methodologies to create C–N bonds via more environmentally friendly and selective routes.
Our laboratory is working on an alternative route called “transfer carboamination of alkenes,” starting from alkenes and O-acylated hydroxylamines R2NOCOR’. The latter can be obtained by simple condensation of the corresponding hydroxylamine R2NOH and esters derivatives. The transformation is both step and atom-economical since two bonds are created in only one step, with the sole release of CO2 as a by-product. Noteworthy, when starting with bio-based ester derivatives, the produced CO₂ will be integrated into the natural carbon cycle, contributing to the overall sustainability of the process.
The objective of the master internship will be to develop an innovative photocatalytic transfer carboamination of alkenes using iron-based photocatalysts. The process will ultimately be applied to synthetic targets such as Venlafaxine or Baclofen.
Location
CEA Saclay, 91 Essonne, France
Internship conditions
- Internship duration: 6 months
- Level of study: Bac+5
- Training: Master 2
- Continuation in PhD thesis: Yes
- Application deadline: 6 janvier 2025
Experimental skills
Language : English
Useful methods and technics:
The internship project will draw on ongoing research in our laboratory on decarboxylative cross-coupling reactions, photocatalysis, and the reactivity of N–O bonds. The student will develop his/her skills in photocatalysis, organic, and organometallic synthesis working under an inert atmosphere (Schlenk lines, gloveboxes) and in the analysis of chemical compounds (NMR, GC, HPLC-MS, IR, X-Ray). Following a knowledge-driven approach, our laboratory also devotes a part of its research to mechanistic studies (experimental studies coupled with DFT computations). The intern will thus have the possibility to be trained in these experiments.
Computer languages and software:
NA
Supervisor
Lucile Anthore-Dalion
Phone: +33169089159
Email :