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)
Very grateful to be selected as member of the Early Career Advisory Board of Tetrahedron and Tetrahedron Letters. Looking forward for exciting new adventures! @ELSchemistry @LIMA_UMR7042 @INC_CNRS @unistra @UHA68 @TetrahedronChem https://www.journals.elsevier.com/tetrahedron-letters/editorial-board/vincent-bizet-phd
A few spots remain for the best live conference you’ll attend: 18th Meeting of the French American Chemical Society June 12–16, 2022 in sunny #CharlestonSC at the lovely #HotelEmeline! Register: http://facs-symposium.unistra.fr *TODAY*! #DrugDiscovery #NewTechnologies #OrganicChemistry
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
Very grateful to be selected as member of the Early Career Advisory Board of Tetrahedron and Tetrahedron Letters. Looking forward for exciting new adventures! @ELSchemistry @LIMA_UMR7042 @INC_CNRS @unistra @UHA68 @TetrahedronChem https://www.journals.elsevier.com/tetrahedron-letters/editorial-board/vincent-bizet-phd
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)
Félicitations Xavier, une reconnaissance plus que méritée!!!
Congratulations to our colleague @BizetVincent who has been nominated member of the early advisory board of Tetrahedron Letters @ELSchemistry. @CNRS_Alsace @UHA68 @unistra @INC_CNRS https://www.journals.elsevier.com/tetrahedron-letters/editorial-board/vincent-bizet-phd
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!