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Ph.D. in organic chemistry (M/F) : Catalytic C(sp3)-H amination

This offer is available in the following languages:
Français - Anglais

Date Limite Candidature : mercredi 13 juillet 2022

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General information

Reference : UPR2301-PHIDAU-003
Workplace : GIF SUR YVETTE
Date of publication : Wednesday, June 22, 2022
Scientific Responsible name : Philippe DAUBAN
Type of Contract : PhD Student contract / Thesis offer
Contract Period : 36 months
Start date of the thesis : 1 November 2022
Proportion of work : Full time
Remuneration : 2 135,00 € gross monthly

Description of the thesis topic

Alkanes represent a major carbon-based feedstock that, paradoxically, remain very rarely used in organic synthesis. Their lack of reactivity makes their transformation energetically demanding thus poorly selective. Accordingly, the conversion of alkanes to higher-value products requires to design new transformations enabling the site-selective introduction of a functional group into their carbon framework. Catalytic C-H activation processes have recently emerged as new efficient methods in organic synthesis. Their application to alkanes, however, remains highly challenging because of the lack of any directing group able to control the selectivity of the reactions.

In this context, the proposal targets the development of a reagent- and catalyst-controlled approach for the selective intermolecular C(sp3)-H amination of alkanes. These reactions will involve the C(sp3)-H insertion of metal-bound nitrenes that will be generated by an oxidative process in the presence of iodine(III) reagents. Novel catalysts (dirhodium(II) complexes) and nitrene sources (sulfamates) will be designed such as they will induce the in situ formation of sufficiently discriminating rhodium-bound nitrene species and lead to on-demand functionalization of primary, secondary, or tertiary C-H bonds.
The project, ultimately, should demonstrate that alkanes are valuable synthons in total synthesis.

The candidate should have a strong background in organic and organometallic chemistry. He/She candidate should be able to work independently, with a sense of adaptability and creativity. He/she should also enjoy working in a team, on a collaborative project with ICMMO-Paris Saclay University, and in a multicultural environment.
A cover letter with a CV, along with transcripts of marks for the two years of Master will be required. A letter of recommendation will be also highly appreciated.

Work Context

-The thesis will take place at the “Institut de Chimie des Substances Naturelles” (ICSN) in Gif-sur-Yvette, a dedicated CNRS laboratory that offers an expertise in organic chemistry, catalysis and biology. ICSN is part of the University of Paris-Saclay located in the southern suburban area of Paris. It operates as an Institute of 4 research departments, supported by a high level of scientific and technical services. A highly-qualified human potential (>80 persons, including research and technical staff) provides advanced training in research for about 70 students, doctoral candidates and post-doctoral fellows in close partnership with a number of public and private enterprises in France, Europe, and over the world.
The ICSN is very well equipped with a large number of NMR spectrometers, X-ray automatic diffractometers, GC/MS and LC/MS equipment.
The candidate will integrate the “Catalyse Organométallique et Synthèse de Molécules Fonctionnelles” research group, composed of 2 permanent researchers and 3 students, inside the department of “Synthèse Organique et Méthodes Catalytiques ».

Constraints and risks

Risks related to research work in a chemistry-biology laboratory

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