Permanent Staff: Armen Panossian, Arlette Klein, Frédéric Leroux*

Team:ChimieOrganiqueetHétérochimieAppliquées(COHA)

Laboratoired’InnovationMoléculaireetApplications,UMR7042-LIMA,ECPMUniversitédeStrasbourg,UniversitédeHaute-AlsaceetCNRS,

25RueBecquerel,67087Strasbourg, Francecoha.unistra.fr

JointCNRS-BayerLaboratoryOrganofluorineChemistry(LCRC2OF)

Chimie Organique et Hétérochimie Appliquées(Dr. Frédéric R. Leroux)

coha.unistra.fr

XA B

Y *P

Y

R1

R1 R2

R3 R4

*

Nouvelles méthodes de synthèse

Contrôle de la chiralité

Catalyse

Agrochimie

Chimie médicinale

...

HeterocyclesbearingEmergentFluorinatedSubstituents(EFS)

Subjects

1.FirstmodularandindustriallyapplicablesynthesisofOCF3-Heterocycles,X-raydiffractionstudies,quantumchemicalcalculations(pKa,dipole,logP,…)

Development of novel methods to build heterocycles with EFS

Collaborations&granting

Novel OCF3-Pyridine Building Blocks

17

NCl

OCF3

I

NBr

OCF3

NI

OCF3

NCl

OCF3COOH

NCl

OCF3NH2

NCl OCF3

NCl OCF3

COOH

NCl OCF3

I

N OCF3

COOH

NHOOC

OCF3

N OCF3Cl

I

N Cl

OCF3

N OCF3Cl

NH2

N Cl

OCF3

I

NCl

OCF3

COOH

N

OCF3COOH

N

OCF3

Br

NCl

OCF3

N OCF3

COOHH2N

A Very successful and flexible approach: dozens of new OCF3 containing pyridines delivered to Bayer up to 100g scale.

2. Use of Fluoroalkyl Amino Reagents (FAR) for the synthesis of fluoroalkyl-substituted heterocycles

3. Stereoselective introduction of OCF3, CHF2, SF5 onto C(sp3)centers

4. Photocatalytic introduction of EFS

CNRS I UMR 7509 I Frédéric Leroux

Quantum Chemistry Calculations of OCF3-Pyridines

Eur. J. Org. Chem. 2010, 6043. Curr. Top. Med. Chem. 2014, 14, 941-51.

Quantum Chemistry Calculations for 2-OCF3-Pyridines

18

Møller-Plesset MP2/TZVPP basis set, gas phase

Eur. J. Org. Chem. 2010, 6043. Curr. Top. Med. Chem. 2014, 14, 941-51.P. Genix, 2010