The objective of the DEFIS project is to developp efficient synthetic methods allowing access to a wide variety of compounds incorporating an emerging fluorinated group, with a special focus in our group on the pentafluorosulfanyl substituent. The interest of the new structures prepared will be demonstrated by their application in a wide range of chemical reactions which should lead to nitrogenous heterocycles substituted by the SF5 group and also allow to deepen the fundamental knowledge relating to the reactivity of organic compounds substituted with this emerging fluorinated group.
This project is funded by the Agence Nationale de la Recherche (ANR-17-CE07-0008)
Several recent reports outlined the singular reactivity of acid fluorides as excellent electrophiles in transition‐metal catalysis. These species undergo oxidative addition of the metal into the C−F bond; then, retention or release of the CO moiety can occur and be controlled by tuning the catalytic system and the reaction parameters. Acid fluorides, which can be derived from carboxylic acids, show good stability and high reactivity in a wide range of possible functionalizations with nucleophiles. Their use provides an interesting alternative to that of the parent carboxylic acid derivatives (acid chlorides, esters, amides, acids, or aldehydes).
Angew. Chem. Int. Ed. 2019, 58, 6814-6817 (link)
Structural diversity in heterocyclic chemistry is key to unlock new properties and modes of action. In this regard, heterocycles embedding emerging fluorinated substituents hold great promises. Herein is described a strategy to access 2-SF5-(aza)indoles for the first time. The sequence relies on the radical addition of SF5Cl to the alkynyl Π-system of 2-ethynyl anilines followed by a cyclization reaction. A telescoped sequence is proposed making this strategy very appealing and reproducible on gram scale. Downstream functionalizations are also demonstrated, allowing an easy diversification of N- and C3-positions. Ames test, pKa, logP and DSC measurements of several fluorinated 2-Rf-indoles are also disclosed. These studies highlight the strategic advantages that a C2-pentafluorosulfanylated motif impart to a privileged scaffold such as indole.
ACS Org. Inorg. Au 2021, DOI:10.1021/acsorginorgau.1c00010 (link)
In “Process Development of a Novel Route to Rilpivirine Hydrochloride” Laurent Petit of #Minakem presents the transformation of initial lab-scale synthetic procedures into a pilot-scale process. #Rilpivirine #HIVTreatment #FACSXVIII
In “Accelerating the Design-Make-Test-Analyse Cycle, Which Technologies to Use and for What Purpose” Laure Haberkorn @Servier discusses how #AI, #MachineLearning, #FlowChemistry & other technologies can accelerate drug discovery & how to overcome challenges they bring. #FACSXVIII
1st 12-month post-doc offer in our new team "Catalyse Organique" at @LIMA_UMR7042 in Strasbourg. Funding from @Fondation_FRC for this project on the enantioselective synthesis of atropisomers. For details and applications, see: https://euraxess.ec.europa.eu/jobs/785624 . Thanks for the retweet
Please check our latest contribution just accepted @angewnandte. We succeeded to design a new reagent able to perform deoxyfluorination of CO2 as well as C-SF5 bond formation.
https://onlinelibrary.wiley.com/doi/abs/10.1002/anie.202204623#.Ymf445d8TsE.twitter
Nous allons bénéficier d’un financement de thèse pour octobre 2022 intitulé « Déaromatisation électrochimique d’azahétérocycles par voie radicalaire ». Si vous êtes intéressés vous pouvez trouver plus de détails sur le site du COBRA (https://www.lab-cobra.fr/wp-content/uploads/2022/03/Thèse-Rouen-2022-pour-diffusion.pdf)
You still have two weeks to apply, after it'll be too late ... Time is running! @RealTimeChem #PhDposition #Organicchemistry #Fluorinechemistry.
Aujourd'hui le LIMA @CNRS_Alsace recevait des étudiants du lycée Jean Rostand de @acstrasbourg pour une visite des laboratoires et un échange avec des élève ultra motivés. Mention spéciale à leur professeur passionné!
The @Leroux_group @LIMA_UMR7042 can be also seen at the poster sessions of the French Congress on Fluorine Chemistry #CFCF2022 with posters from Lilian Wisson, Nicolas Moget and @FlorianAudet
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