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Start Over Author "Shuxin Mao" Topic 010402 general chemistry
5 results on '"Shuxin Mao"'

1. Exploring Green Solvents Associated to Pd/C as Heterogeneous Catalyst for Direct Arylation of Heteroaromatics with Aryl Bromides

Author

Xinzhe Shi, Jean-François Soulé, Shuxin Mao, Henri Doucet, 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), CNRS, ANR, ANR-16-CE07-0001,ALCATRAS,Ligands hybrides modulables en catalyse d'activation de liaisons stables C–H et C–O(2016), 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
Heterogeneous catalysis, [CHIM.ORGA]Chemical Sciences/Organic chemistry, 010405 organic chemistry, Chemistry, Aryl, chemistry.chemical_element, Direct arylation, [CHIM.CATA]Chemical Sciences/Catalysis, General Chemistry, 010402 general chemistry, 01 natural sciences, Combinatorial chemistry, 0104 chemical sciences, C-H bond activation, chemistry.chemical_compound, 13. Climate action, Atom economy, Green solvents, Palladium
Abstract

International audience; Metal residues are certainly one of the major sources of contamination of products in metal-catalyzed direct arylation reactions. We found that the use of only 1 mol% of the heterogeneous catalyst Pd/C promotes very efficiently the direct arylations of most heteroaromatics. In the presence of this catalyst and potassium acetate as the base, the direct arylation of thiophenes, furans, pyrroles, thiazoles, imidazoles or isoxazoles, using aryl bromides as coupling partners, proceeds highly regioselectively and in moderate to very high yields. With several heteroarenes both electron-deficient and electron-rich aryl bromides were tolerated; moreover, with the most reactive heteroarenes, the Pd/C catalyst tolerated green solvents such as diethyl carbonate, 3-methylbutan-1-ol and pentan-1-ol, affording a synthetic scheme with low environmental impact.

Published
2018
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2. Palladium-catalyzed successive C-H bond arylations and annulations toward the pi-extension of selenophene-containing aromatic skeletons

Author

Xinzhe Shi, Shuxin Mao, Henri Doucet, Jean-François Soulé, Thierry Roisnel, 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), ANR [ANR-16-CE07-0001], ANR-16-CE07-0001,ALCATRAS,Ligands hybrides modulables en catalyse d'activation de liaisons stables C–H et C–O(2016), 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
C h bond, 010405 organic chemistry, Chemistry, Aryl, Organic Chemistry, chemistry.chemical_element, 010402 general chemistry, 01 natural sciences, Medicinal chemistry, 0104 chemical sciences, Catalysis, chemistry.chemical_compound, Molecule, [CHIM]Chemical Sciences, Palladium
Abstract

International audience; A modular approach for the synthesis of planar pi-extended selenium containing molecules from selenophene has been developed. Different combinations of Pd-catalyzed desulfitative C-H bond arylations with (2-bromo)arylsulfonyl chlorides and Pd-catalyzed intra- or/and inter-molecular C-H bond arylations with aryl bromides allowed the extension of the selenophene-containing aromatic skeleton at the [b]-, [c]- or [bd]-junctions to give phenanthro[b]selenophenes, phenanthro[c]selenophenes or diphenanthro[bd]selenophenes.

Published
2019
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3. Pd/C as Heterogeneous Catalyst for the Direct Arylation of (Poly)fluorobenzenes

Author

Henri Doucet, Shuxin Mao, Xinzhe Shi, Jean-François Soulé, 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), ANR-16-CE07-0001,ALCATRAS,Ligands hybrides modulables en catalyse d'activation de liaisons stables C–H et C–O(2016), 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
Nitrile, 010402 general chemistry, Heterogeneous catalysis, 01 natural sciences, Medicinal chemistry, Catalysis, C−H activation, chemistry.chemical_compound, fluorine, arylation, Trifluoromethyl, 010405 organic chemistry, [CHIM.ORGA]Chemical Sciences/Organic chemistry, Aryl, Organic Chemistry, Fluorobenzene, C−C coupling, Regioselectivity, General Chemistry, [CHIM.CATA]Chemical Sciences/Catalysis, palladium, 0104 chemical sciences, heterogeneous catalysis, chemistry, Phosphine
Abstract

International audience; The potential of the heterogeneous catalyst 10 % Pd/C in the direct arylation of (poly)fluorobenzene derivatives with aryl bromides has been investigated. In general, high yields of biaryl derivatives were obtained by using tri-, tetra-, and pentafluorobenzenes, whereas mono- and difluorobenzenes exhibited poor reactivity. The regioselectivities of the arylation reactions were similar to those observed with homogeneous palladium catalysts. Both electron-withdrawing and -donating substituents, such as nitrile, nitro, acetyl, ester, trifluoromethyl, tert-butyl, methoxy, or methyl, on the aryl bromide were tolerated. Unexpectedly, tetrafluoro-substituted [1,1′-biphenyl]-4-ols were obtained from pentafluorobenzene at 150 °C due to a formal regioselective hydroxylation, whereas at lower temperatures the expected pentafluorobiphenyls were obtained. However, no C−F bond cleavage was observed with the other polyfluorobenzene derivatives. These arylation reactions were carried out with only 1 mol % Pd/C as the catalyst and KOAc as an inexpensive base. Therefore, this protocol represents a very attractive access to (poly)fluoro-substituted biphenyls in terms of cost, simplicity, and sustainable chemistry because the Pd/C catalyst can be easily removed at the end of the reaction, there is no contamination with phosphine ligand residues, and the major side-product of the reaction is KOAc⋅HBr.

Published
2019
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4. Environmentally Benign Arylations of 5-Membered Ring Heteroarenes by Pd-Catalyzed C−H Bonds Activations

Author

Xinzhe Shi, Haoran Li, Shuxin Mao, Henri Doucet, Jean-François Soulé, 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), We thank China Scholarship Council for providing financial support to H. L. and ANR for providing financial support to X. S., 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 ANR-16-CE07-0001,ALCATRAS,Ligands hybrides modulables en catalyse d'activation de liaisons stables C–H et C–O(2016)

Subjects
Green chemistry, chemistry.chemical_element, 010402 general chemistry, Ring (chemistry), 01 natural sciences, Catalysis, Inorganic Chemistry, chemistry.chemical_compound, arylation, Physical and Theoretical Chemistry, green solvents, C−H bond activation, Reaction conditions, catalysis, 010405 organic chemistry, [CHIM.ORGA]Chemical Sciences/Organic chemistry, Aryl, Organic Chemistry, Regioselectivity, heteroarenes, [CHIM.CATA]Chemical Sciences/Catalysis, palladium, Combinatorial chemistry, 0104 chemical sciences, chemistry, Palladium
Abstract

International audience; The palladium‐catalyzed functionalization of 5‐membered ring heteroaromatics, through a C−H bonds activation, for access to arylated heteroaromatics represent a very attractive alternative to more classical cross‐coupling reactions, as it saves steps and reduces the amount of wastes. Despite these advantages, these transformations initially suffered from major limitations in terms of sustainable chemistry concerning the reaction media, the nature of the catalyst, the catalyst loading, the aryl source or the regioselectivity control. Tremendous improvements allowing more sustainable reaction conditions using greener solvents, new aryl sources or employing easily removable catalysts and lower catalyst loadings have been described during the last decades. This review summarizes some of the most important contributions made in these directions.

Published
2019
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5. Reactivity of 1,2,3- and 1,2,4-Trifluorobenzenes in Palladium-Catalyzed Direct Arylation

Author

Shuxin Mao, Xinzhe Shi, Jean-François Soulé, Henri Doucet, 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), Agence Nationale de la Recherche, Centre National de la Recherche Scientifique, Rennes M?tropole, 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 ANR-16-CE07-0001,ALCATRAS,Ligands hybrides modulables en catalyse d'activation de liaisons stables C–H et C–O(2016)

Subjects
Reaction conditions, chemistry.chemical_classification, Base (chemistry), 010405 organic chemistry, [CHIM.ORGA]Chemical Sciences/Organic chemistry, Organic Chemistry, Regioselectivity, chemistry.chemical_element, [CHIM.CATA]Chemical Sciences/Catalysis, 010402 general chemistry, 01 natural sciences, Combinatorial chemistry, 0104 chemical sciences, Catalysis, chemistry, Surface modification, Reactivity (chemistry), ComputingMilieux_MISCELLANEOUS, Palladium
Abstract

The higher reactivity of the C4-H bond as compared to the C5-H bond of 1,2,3-trifluorobenzene in palladium-catalyzed direct arylation allows the selective synthesis of 4-aryl-1,2,3-trifluorobenzenes in moderate to high yields. In most cases, phosphine-free Pd(OAc)2 catalyst and inexpensive KOAc base were employed. Then, from these 4-aryl-1,2,3-trifluorobenzenes, the palladium-catalyzed C–H bond functionalization of the C6-position allows the synthesis of the corresponding 4,6-diarylated 1,2,3-trifluorobenzenes. We also applied these reaction conditions to the regioselective direct C3-arylation of 1,2,4-trifluorobenzene.

Published
2018
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