title: Pd(0)-Catalyzed Direct C-H Functionalization of 2-H-4-Benzylidene Imidazolones: Friendly and Large-Scale Access to GFP and Kaede Protein Fluorophores.
abstract: The first one-pot synthesis of N-substituted 2-H-4-benzylidene imidazolones and their subsequent palladium-catalyzed and copper-assisted direct C2-H arylation and alkenylation with aryl- and alkenylhalides are described. This innovative synthesis is step-economical, azide-free, high yielding, highly flexible in the introduction of a variety of electronically different groups, and can be operated on large-scale. Moreover, the method allows direct access to C2-arylated or alkenylated imidazolone-based green fluorescent protein (GFP) and Kaede protein fluorophores, including ortho-hydroxylated models.
authors.affiliation: Normandie Univ, COBRA, UMR 6014 et FR 3038, Univ Rouen; INSA Rouen; CNRS, IRCOF, 1 rue Tesnière, 76821, Mont Saint Aignan Cedex, France.
authors.forename: Mickaël
authors.initials: M
authors.lastname: Muselli
authors.affiliation: Normandie Univ, COBRA, UMR 6014 et FR 3038, Univ Rouen; INSA Rouen; CNRS, IRCOF, 1 rue Tesnière, 76821, Mont Saint Aignan Cedex, France.
authors.forename: Christine
authors.initials: C
authors.lastname: Baudequin
authors.affiliation: CNRS, UMR6301-ISTCT et FR 3038, LDM-TEP, CEA-DSV/I2BM, UNICAEN, Normandie Univ, GIP CYCERON, 14074, Caen, France.
authors.forename: Cécile
authors.initials: C
authors.lastname: Perrio
authors.affiliation: Normandie Univ, COBRA, UMR 6014 et FR 3038, Univ Rouen; INSA Rouen; CNRS, IRCOF, 1 rue Tesnière, 76821, Mont Saint Aignan Cedex, France. christophe.Hoarau@insa-rouen.fr.
authors.forename: Christophe
authors.initials: C
authors.lastname: Hoarau
authors.affiliation: Normandie Univ, COBRA, UMR 6014 et FR 3038, Univ Rouen; INSA Rouen; CNRS, IRCOF, 1 rue Tesnière, 76821, Mont Saint Aignan Cedex, France. laurent.bischoff@insa-rouen.fr.
authors.forename: Laurent
authors.initials: L
authors.lastname: Bischoff
mesh_terms: D001597:Benzylidene Compounds / Q000737:chemistry*; D002384:Catalysis; D003300:Copper / Q000737:chemistry; D049452:Green Fluorescent Proteins / Q000138:chemical synthesis* / Q000737:chemistry*; D007093:Imidazoles / Q000737:chemistry*; D015394:Molecular Structure; D010165:Palladium / Q000737:chemistry
chemical_list: D001597:Benzylidene Compounds; D007093:Imidazoles; C117197:imidazolone; D049452:Green Fluorescent Proteins; D010165:Palladium; D003300:Copper
keywords: arylation; cooperative catalysis; cross-coupling; organic materials; palladium