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1. Synthesis of Unsymmetrical Heterobiaryls Using Palladium-Catalyzed Cross-Coupling Reactions of Lithium Organozincates

Author

Anny Jutand, Florence Mongin, Anne Seggio, Ghislaine Priem, Chimie et Photonique Moléculaires (CPM), Université de Rennes 1 (UR1), Université de Rennes (UNIV-RENNES)-Université de Rennes (UNIV-RENNES)-Centre National de la Recherche Scientifique (CNRS), Processus d'Activation Sélective par Transfert d'Energie Uni-électronique ou Radiatif (UMR 8640) (PASTEUR), Université Pierre et Marie Curie - Paris 6 (UPMC)-Département de Chimie - ENS Paris, École normale supérieure - Paris (ENS Paris), Université Paris sciences et lettres (PSL)-Université Paris sciences et lettres (PSL)-École normale supérieure - Paris (ENS Paris), Université Paris sciences et lettres (PSL)-Université Paris sciences et lettres (PSL)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), GlaxoSmithKline, GlaxoSmthKline, Université de Rennes (UR)-Centre National de la Recherche Scientifique (CNRS), École normale supérieure - Paris (ENS-PSL), and Université Paris sciences et lettres (PSL)-Université Paris sciences et lettres (PSL)-École normale supérieure - Paris (ENS-PSL)

Subjects
010405 organic chemistry, Stereochemistry, Metalation, zinc, Organic Chemistry, chemistry.chemical_element, metalation, [CHIM.CATA]Chemical Sciences/Catalysis, Zinc, palladium, 010402 general chemistry, 01 natural sciences, Coupling reaction, 0104 chemical sciences, Catalysis, Transmetalation, chemistry, Polymer chemistry, cross-coupling, Lithium, heterocycle, Palladium
Abstract

International audience; Several unsymmetrical heterobiaryls have been synthesized through palladium-catalyzed cross-coupling reactions of lithium triorganozincates. The latter have been prepared by deprotonative lithiation followed by transmetalation using non hygroscopic ZnCl2*TMEDA (1/3 equiv).

Published
2008
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2. Lithium-Mediated Zincation of Pyrazine, Pyridazine, Pyrimidine, and Quinoxaline

Author

Floris Chevallier, Florence Mongin, Michel Vaultier, Anne Seggio, Chimie et Photonique Moléculaires (CPM), Université de Rennes (UR)-Centre National de la Recherche Scientifique (CNRS), Synthèse et électrosynthèse organiques (SESO), Université de Rennes 1 (UR1), Université de Rennes (UNIV-RENNES)-Université de Rennes (UNIV-RENNES)-Centre National de la Recherche Scientifique (CNRS), Institut des Sciences Chimiques de Rennes (ISCR), Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC)-Université de Rennes 1 (UR1), Université de Rennes (UNIV-RENNES)-Université de Rennes (UNIV-RENNES)-Ecole Nationale Supérieure de Chimie de Rennes (ENSCR)-Institut National des Sciences Appliquées - Rennes (INSA Rennes), Institut National des Sciences Appliquées (INSA)-Université de Rennes (UNIV-RENNES)-Institut National des Sciences Appliquées (INSA), Institut des Sciences Moléculaires (ISM), Centre National de la Recherche Scientifique (CNRS)-École Nationale Supérieure de Chimie et de Physique de Bordeaux (ENSCPB)-Université Sciences et Technologies - Bordeaux 1-Université Montesquieu - Bordeaux 4-Institut de Chimie du CNRS (INC), Université de Rennes (UR)-Institut National des Sciences Appliquées - Rennes (INSA Rennes), Institut National des Sciences Appliquées (INSA)-Institut National des Sciences Appliquées (INSA)-Ecole Nationale Supérieure de Chimie de Rennes (ENSCR)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), and Université Montesquieu - Bordeaux 4-Université Sciences et Technologies - Bordeaux 1 (UB)-École Nationale Supérieure de Chimie et de Physique de Bordeaux (ENSCPB)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)

Subjects
Magnetic Resonance Spectroscopy, Pyrazine, Pyrimidine, Dimer, Lithium, 010402 general chemistry, Photochemistry, 01 natural sciences, Medicinal chemistry, Mass Spectrometry, Pyridazine, chemistry.chemical_compound, Quinoxaline, Deprotonation, Quinoxalines, ComputingMilieux_MISCELLANEOUS, [CHIM.ORGA]Chemical Sciences/Organic chemistry, 010405 organic chemistry, Organic Chemistry, 0104 chemical sciences, Pyridazines, Solvent, Zinc, Pyrimidines, chemistry, Pyrazines, Derivative (chemistry)
Abstract

International audience; Deprotonation of pyrazine, pyridazine, pyrimidine, and quinoxaline using an in situ mixture of ZnCl2.TMEDA (0.5 equiv) and LiTMP (1.5 equiv) was studied. Pyrazine and pyrimidine were deprotonated in THF at room temperature, a result evidenced by trapping with I2. The competitive formation of dimer observed in net hexane was reduced by using cosolvents (TMEDA or THF). Starting from quinoxaline, the dimer formation took place in THF also, and mixtures of mono- and diiodides were obtained whatever the solvent and conditions used. A similar competitive formation of a diiodide was noted with pyridazine; the use of THF at reflux temperature nevertheless afforded the 3-iodo derivative in good yield.

Published
2007
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3. ChemInform Abstract: Palladium-Catalyzed Cross-Couplings of Lithium Arylzincates with Aromatic Halides: Synthesis of Analogues of Isomeridianin G and Evaluation as GSK-3β Inhibitors

Author

Floris Chevallier, Ghislaine Priem, Florence Mongin, and Anne Seggio

Subjects
Transmetalation, chemistry, chemistry.chemical_element, Halide, Lithium, General Medicine, Combinatorial chemistry, Catalysis, Palladium
Abstract

Several analogues of isomeridianin G have been synthesized using palladium-catalyzed cross-coupling reactions of lithium triorganozincates as a key step. The latter have been prepared by deprotonative lithiation followed by transmetalation using ZnCl 2 TMEDA (0.33 equiv).

Published
2010
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4. Palladium-Catalyzed Cross-couplings of Lithium Arylzincates with Aromatic Halides. Synthesis of Analogues of Isomeridianin G and Evaluation as GSK- 3 Inhibitors

Author

Florence Mongin, Floris Chevallier, Ghislaine Priem, Anne Seggio, Synthèse et électrosynthèse organiques (SESO), Université de Rennes 1 (UR1), Université de Rennes (UNIV-RENNES)-Université de Rennes (UNIV-RENNES)-Centre National de la Recherche Scientifique (CNRS), GlaxoSmithKline, GlaxoSmthKline, Chimie et Photonique Moléculaires (CPM), Institut des Sciences Chimiques de Rennes (ISCR), Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC)-Université de Rennes 1 (UR1), Université de Rennes (UNIV-RENNES)-Université de Rennes (UNIV-RENNES)-Ecole Nationale Supérieure de Chimie de Rennes (ENSCR)-Institut National des Sciences Appliquées - Rennes (INSA Rennes), Institut National des Sciences Appliquées (INSA)-Université de Rennes (UNIV-RENNES)-Institut National des Sciences Appliquées (INSA), Université de Rennes (UR)-Centre National de la Recherche Scientifique (CNRS), Université de Rennes (UR)-Institut National des Sciences Appliquées - Rennes (INSA Rennes), and Institut National des Sciences Appliquées (INSA)-Institut National des Sciences Appliquées (INSA)-Ecole Nationale Supérieure de Chimie de Rennes (ENSCR)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)

Subjects
010405 organic chemistry, [CHIM.ORGA]Chemical Sciences/Organic chemistry, Organic Chemistry, Halide, chemistry.chemical_element, Zinc, 010402 general chemistry, 01 natural sciences, Combinatorial chemistry, Catalysis, 0104 chemical sciences, Transmetalation, chemistry, Organic chemistry, Lithium, Palladium
Abstract

International audience; Several analogues of Isomeridianin G have been synthesized using as a key step palladium-catalyzed crosscoupling reactions of lithium triorganozincates. The latter have been prepared by deprotonative lithiation followed by transmetalation using ZnCl2*TMEDA (1/3 equiv).

Published
2009
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5. ChemInform Abstract: Deprotonative Metalation of Five-Membered Aromatic Heterocycles Using Mixed Lithium-Zinc Species

Author

Mitsuhiro Yonehara, Masanobu Uchiyama, Erwann Jeanneau, Floris Chevallier, Jean‐Martial L'Helgoual'ch, Anne Seggio, and Florence Mongin

Subjects
chemistry.chemical_compound, Deprotonation, Lithium amide, chemistry, Benzothiazole, Metalation, Furan, Thiophene, General Medicine, Benzoxazole, Medicinal chemistry, Pyrrole
Abstract

Deprotonation of benzoxazole, benzothiazole, benzo[b]thiophene, benzo[b]furan, N-Boc-protected indole and pyrrole, and N-phenylpyrazole using an in situ mixture of ZnCl(2).TMEDA (0.5 equiv) and lithium 2,2,6,6-tetramethylpiperidide (1.5 equiv) in THF at room temperature is described. The reaction was evidenced by trapping with iodine, regioselectively giving the expected functionalized derivatives in 52-73% yields. A mixture of mono- and disubstituted derivatives was obtained starting from thiazole. Cross-coupling reactions of 2-metalated benzo[b]thiophene and benzo[b]furan with heteroaromatic chlorides proved possible under palladium catalysis. A reaction pathway where the lithium amide and zinc diamide present in solution behave synergically was proposed for the deprotonation reaction, taking account of NMR and DFT studies carried out on the basic mixture.

Published
2008
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6. Deprotonative metalation of five-membered aromatic heterocycles using mixed lithium-zinc species

Author

Mitsuhiro Yonehara, Florence Mongin, Floris Chevallier, Erwann Jeanneau, Anne Seggio, Masanobu Uchiyama, Jean‐Martial L'Helgoual'ch, Chimie et Photonique Moléculaires (CPM), Université de Rennes (UR)-Centre National de la Recherche Scientifique (CNRS), Synthèse et électrosynthèse organiques (SESO), Institut des Sciences Chimiques de Rennes (ISCR), Université de Rennes (UR)-Institut National des Sciences Appliquées - Rennes (INSA Rennes), Institut National des Sciences Appliquées (INSA)-Institut National des Sciences Appliquées (INSA)-Ecole Nationale Supérieure de Chimie de Rennes (ENSCR)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), RIKEN - Institute of Physical and Chemical Research [Japon] (RIKEN), Université Claude Bernard Lyon 1 (UCBL), Université de Lyon, RIKEN Center for Brain Science [Wako] (RIKEN CBS), Université de Rennes 1 (UR1), Université de Rennes (UNIV-RENNES)-Université de Rennes (UNIV-RENNES)-Centre National de la Recherche Scientifique (CNRS), Université de Rennes (UNIV-RENNES)-Université de Rennes (UNIV-RENNES)-Institut National des Sciences Appliquées - Rennes (INSA Rennes), and Institut National des Sciences Appliquées (INSA)-Université de Rennes (UNIV-RENNES)-Institut National des Sciences Appliquées (INSA)-Ecole Nationale Supérieure de Chimie de Rennes (ENSCR)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)

Subjects
Lithium amide, Molecular Structure, [CHIM.ORGA]Chemical Sciences/Organic chemistry, 010405 organic chemistry, Metalation, Hydrocarbons, Halogenated, Organic Chemistry, Stereoisomerism, Benzoxazole, Lithium, 010402 general chemistry, 01 natural sciences, Medicinal chemistry, 0104 chemical sciences, chemistry.chemical_compound, Zinc, Deprotonation, chemistry, Benzothiazole, Heterocyclic Compounds, Furan, Thiophene, Organometallic Compounds, Organic chemistry, Pyrrole
Abstract

International audience; Deprotonation of benzoxazole, benzothiazole, benzo[b]thiophene, benzo[b]furan, N-Boc protected indole and pyrrole, and N-phenylpyrazole using an in situ mixture of ZnCl2*TMEDA (0.5 equiv) and lithium 2,2,6,6-tetramethylpiperidide (1.5 equiv) in THF at room temperature was described. The reaction was evidenced by trapping with iodine, regioselectively giving the expected functionalized derivatives in 52 to 73% yields. A mixture of mono- and disubstituted derivatives was obtained starting from thiazole. Cross-coupling reactions of 2-metalated benzo[b]thiophene and benzo[b]furan with heteroaromatic chlorides proved possible under palladium catalysis. A reaction pathway where the lithium amide and zinc diamide present in solution behave synergically was proposed for the deprotonation reaction, taking account of NMR and DFT studies carried out on the basic mixture.

Published
2007
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7. Ligand-Activated Lithium-Mediated Zincation of N-Phenylpyrrole

Author

Anne Seggio, Stéphane Golhen, Thierry Roisnel, Masanobu Uchiyama, Floris Chevallier, Florence Mongin, Marie-Isabelle Lannou, Daisuke Nobuto, CPM - Chimie et Photonique Moléculaires, Chimie et Photonique Moléculaires (CPM), Université de Rennes 1 (UR1), Université de Rennes (UNIV-RENNES)-Université de Rennes (UNIV-RENNES)-Centre National de la Recherche Scientifique (CNRS), RIKEN - Institute of Physical and Chemical Research [Japon] (RIKEN), Institut des Sciences Chimiques de Rennes (ISCR), Université de Rennes (UNIV-RENNES)-Université de Rennes (UNIV-RENNES)-Institut National des Sciences Appliquées - Rennes (INSA Rennes), Institut National des Sciences Appliquées (INSA)-Université de Rennes (UNIV-RENNES)-Institut National des Sciences Appliquées (INSA)-Ecole Nationale Supérieure de Chimie de Rennes (ENSCR)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Synthèse et électrosynthèse organiques (SESO), Université de Rennes (UR)-Centre National de la Recherche Scientifique (CNRS), Université de Rennes (UR)-Institut National des Sciences Appliquées - Rennes (INSA Rennes), Institut National des Sciences Appliquées (INSA)-Institut National des Sciences Appliquées (INSA)-Ecole Nationale Supérieure de Chimie de Rennes (ENSCR)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), RIKEN Center for Brain Science [Wako] (RIKEN CBS), Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC)-Université de Rennes 1 (UR1), Université de Rennes (UNIV-RENNES)-Université de Rennes (UNIV-RENNES)-Ecole Nationale Supérieure de Chimie de Rennes (ENSCR)-Institut National des Sciences Appliquées - Rennes (INSA Rennes), and Institut National des Sciences Appliquées (INSA)-Université de Rennes (UNIV-RENNES)-Institut National des Sciences Appliquées (INSA)

Subjects
Metalation, chemistry.chemical_element, metalation, zincates, 010402 general chemistry, Ligands, 01 natural sciences, Medicinal chemistry, Catalysis, chemistry.chemical_compound, Organic chemistry, Pyrroles, ligand effects, heterocycles, Molecular Structure, 010405 organic chemistry, [CHIM.ORGA]Chemical Sciences/Organic chemistry, Organic Chemistry, General Chemistry, Tetramethylethylenediamine, Toluene, 0104 chemical sciences, Solvent, Zinc, DMPU, chemistry, Zinc Compounds, lithium, Lithium, Diethyl ether, Selectivity
Abstract

International audience; Metalation of N-phenylpyrrole by using an in situ mixture of ZnCl(2)TMEDA (0.5 equiv; TMEDA=N,N,N',N'-tetramethylethylenediamine) and LiTMP (1.5 equiv; TMP=2,2,6,6-tetramethylpiperidino) was optimized. The reaction carried out at room temperature in THF resulted in incomplete metalation (56 % conversion) and selectivity (mixture of 2-iodo and 2,2'-diiodo derivatives in an 86:14 ratio after trapping with iodine). By using diethyl ether (DEE), toluene, or hexane instead of THF, low conversions of 17, 38, or 23 % were observed, respectively, but the formation of the diiodide was avoided. When hexane was used as solvent, strong lithium-complexing ligands such as [12]crown-4 and N,N'-dimethylpropylideneurea (DMPU) inhibited the reaction whereas more (hemi)labile ligands (TMEDA>THF approximately DME) favored it. This result shows that a temporary accessibility of lithium to interact with the rest of the base and/or the substrate is a prerequisite for an efficient metalation. A 75 % yield of 2-iodo-N-phenylpyrrole was obtained after reaction with the base in the presence of five equivalents of TMEDA for two hours at room temperature, and subsequent trapping with iodine. We were able to successfully replace the spare TMP with a less expensive butyl group.

Published
2007
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