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HMF in Multicomponent Reactions: Efficient Routes Towards Novel Fine Chemicals

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HMF in Multicomponent Reactions: Efficient Routes Towards Novel Fine Chemicals HMF in multicomponent reactions : Efficient routes towards novel fine chemicals Weigang Fan To cite this version: Weigang Fan. HMF in multicomponent reactions : Efficient routes towards novel fine chemicals. Theoretical and/or physical chemistry. Université de Lyon, 2019. English. NNT : 2019LYSEI022. tel-02402915 HAL Id: tel-02402915 https://tel.archives-ouvertes.fr/tel-02402915 Submitted on 10 Dec 2019 HAL is a multi-disciplinary open access L’archive ouverte pluridisciplinaire HAL, est archive for the deposit and dissemination of sci- destinée au dépôt et à la diffusion de documents entific research documents, whether they are pub- scientifiques de niveau recherche, publiés ou non, lished or not. The documents may come from émanant des établissements d’enseignement et de teaching and research institutions in France or recherche français ou étrangers, des laboratoires abroad, or from public or private research centers. publics ou privés. N°d’ordre NNT : 2019LYSEI022 THESE de DOCTORAT DE L’UNIVERSITE DE LYON opérée au sein de L’institut National Des Sciences Appliquées De Lyon Ecole Doctorale N° ED 206 Ecole Doctorale de Chimie de Lyon Spécialité/ discipline de doctorat : Chimie Soutenue publiquement le 05/04/2019, par : Weigang FAN Utilisation du HMF en réactions multicomposantes: accès rapide vers de nouvelles cibles en chimie fine HMF in multicomponent reactions: Efficient routes towards novel fine chemicals Devant le jury composé de : DRAYE Micheline, Professeur des Universités, Université Savoie Mont Blanc, Président LAMATY Frédéric, Directeur de Recherche au CNRS, Université de Montpellier , Rapporteur SAUTHIER Mathieu, Professeur des Universités, Université de Lille 1, Rapporteur DJAKOVITCH Laurent, Directeur de Recherche au CNRS, Université Lyon 1, Examinateur POPOWYCZ Florence, Professeur des Universités, INSA de Lyon, Co-directrice de thèse QUENEAU Yves, Directeur de Recherche au CNRS, Université de Lyon, Directeur de thèse Cette thèse est accessible à l'adresse : http://theses.insa-lyon.fr/publication/2019LYSEI022/these.pdf © [W. Fan], [2019], INSA Lyon, tous droits réservés Cette thèse est accessible à l'adresse : http://theses.insa-lyon.fr/publication/2019LYSEI022/these.pdf © [W. Fan], [2019], INSA Lyon, tous droits réservés Département FEDORA – INSA Lyon - Ecoles Doctorales – Quinquennal 2016-2020 SIGLE ECOLE DOCTORALE NOM ET COORDONNEES DU RESPONSABLE CHIMIE CHIMIE DE LYON M. Stéphane DANIELE Institut de recherches sur la catalyse et l’environnement de Lyon http://www.edchimie-lyon.fr IRCELYON-UMR 5256 Sec. : Renée EL MELHEM Équipe CDFA Bât. Blaise PASCAL, 3e étage 2 Avenue Albert EINSTEIN [email protected] 69 626 Villeurbanne CEDEX INSA : R. GOURDON [email protected] E.E.A. ÉLECTRONIQUE, M. Gérard SCORLETTI ÉLECTROTECHNIQUE, École Centrale de Lyon AUTOMATIQUE 36 Avenue Guy DE COLLONGUE 69 134 Écully http://edeea.ec-lyon.fr Tél : 04.72.18.60.97 Fax 04.78.43.37.17 Sec. : M.C. HAVGOUDOUKIAN [email protected] [email protected] E2M2 ÉVOLUTION, ÉCOSYSTÈME, M. Philippe NORMAND MICROBIOLOGIE, MODÉLISATION UMR 5557 Lab. d’Ecologie Microbienne Université Claude Bernard Lyon 1 http://e2m2.universite-lyon.fr Bâtiment Mendel Sec. : Sylvie ROBERJOT 43, boulevard du 11 Novembre 1918 Bât. Atrium, UCB Lyon 1 69 622 Villeurbanne CEDEX Tél : 04.72.44.83.62 [email protected] INSA : H. CHARLES [email protected] EDISS INTERDISCIPLINAIRE Mme Emmanuelle CANET-SOULAS SCIENCES-SANTÉ INSERM U1060, CarMeN lab, Univ. Lyon 1 Bâtiment IMBL http://www.ediss-lyon.fr 11 Avenue Jean CAPELLE INSA de Lyon Sec. : Sylvie ROBERJOT 69 621 Villeurbanne Bât. Atrium, UCB Lyon 1 Tél : 04.72.68.49.09 Fax : 04.72.68.49.16 Tél : 04.72.44.83.62 [email protected] INSA : M. LAGARDE [email protected] INFOMATHS INFORMATIQUE ET M. Luca ZAMBONI MATHÉMATIQUES Bât. Braconnier 43 Boulevard du 11 novembre 1918 http://edinfomaths.universite-lyon.fr 69 622 Villeurbanne CEDEX Sec. : Renée EL MELHEM Tél : 04.26.23.45.52 Bât. Blaise PASCAL, 3e étage [email protected] Tél : 04.72.43.80.46 [email protected] MATÉRIAUX DE LYON M. Jean-Yves BUFFIÈRE Matériaux INSA de Lyon http://ed34.universite-lyon.fr MATEIS - Bât. Saint-Exupéry Sec. : Stéphanie CAUVIN 7 Avenue Jean CAPELLE Tél : 04.72.43.71.70 69 621 Villeurbanne CEDEX Bât. Direction Tél : 04.72.43.71.70 Fax : 04.72.43.85.28 [email protected] [email protected] MEGA MÉCANIQUE, ÉNERGÉTIQUE, M. Jocelyn BONJOUR GÉNIE CIVIL, ACOUSTIQUE INSA de Lyon Laboratoire CETHIL http://edmega.universite-lyon.fr Bâtiment Sadi-Carnot Sec. : Stéphanie CAUVIN 9, rue de la Physique Tél : 04.72.43.71.70 69 621 Villeurbanne CEDEX Bât. Direction [email protected] [email protected] ScSo ScSo* M. Christian MONTES Université Lyon 2 http://ed483.univ-lyon2.fr 86 Rue Pasteur Sec. : Viviane POLSINELLI 69 365 Lyon CEDEX 07 Brigitte DUBOIS [email protected] INSA : J.Y. TOUSSAINT Tél : 04.78.69.72.76 [email protected] *ScSoCette thèse: Histoire, est Géographie,accessible Aménagement,à l'adresse : http://theses.insa-lyon.fr/publication/2019LYSEI022/these.pdf Urbanisme, Archéologie, Science politique, Sociologie, Anthropologie © [W. Fan], [2019], INSA Lyon, tous droits réservés Cette thèse est accessible à l'adresse : http://theses.insa-lyon.fr/publication/2019LYSEI022/these.pdf © [W. Fan], [2019], INSA Lyon, tous droits réservés Acknowledgement First and foremost, I would like to express my deepest gratitude to my supervisors Dr. Yves QUENEAU and Prof. Florence POPOWYCZ for their generous commitment and help throughout my PhD study. This thesis would not have been completed without their guidance. Florence spent so much time on coaching my bench work and preparing manuscripts for publication. I am deeply impressed by her rigorous attitude to science. Also, her patient guidance, constructive suggestion as well as frank criticism have benefited me a lot. Besides directing my research, Yves taught me how to make a presentation, how to write a scientific paper, also gave me a lot encouragement when I was depressed. Many thanks to both of you for your tolerance and accepting me as I am. It is quite fortunate being your student. I would like to acknowledge Mrs Lucie GRAND for her kind assistance in many aspects, as well as other staff members in COB team: Dr. Sylvie MOEBS, Dr. Maïwenn JACOLOT, Dr. Mohammed AHMAR, Dr. Laurent SOULERE and Dr. Stéphane CHAMBERT. Special thanks go to my former lab mates: Dr. Xiubin LI, Dr. Si-Zhe LI, Dr. Zonglong YANG, for their kind help especially when I just arrived in France. Thanks also need to be given to current lab mates: Dr. Charlie VERRIER (particularly for his help for the preparation of a review manuscript), Dr. Johal RUIZ, Lianjie WANG, Qiang ZHANG, Xiaoyang YUE, Florian BAHE, Eman DOKMAK, Pauline PACQUET, Elise CARTIER, Vincent MAST, Jeremy MAGAND, Kevin CHATEL. I would also like to thank Dr. Anis TLILI and Dr. Nuno MONTEIRO for serving on my annual examination committee in past three years. I also feel grateful to ICBMS for providing resources for my research and study. Special gratitude goes to my thesis jury members: Dr. Laurent DJAKOVITCH (Université Lyon 1), Dr. Frédéric LAMATY (Université de Montpellier), Prof. Mathieu SAUTHIER (Université de Lille 1), Prof. Micheline DRAYE (Université Savoie Mont Blanc), for having kindly agreed to serve on this committee. I also thank the China Scholarship Council (CSC) for providing the fellowship for my study in France. Thanks to my family for their love and support throughout my life. Thanks to all the people who have ever helped me in my life. - 1 - Cette thèse est accessible à l'adresse : http://theses.insa-lyon.fr/publication/2019LYSEI022/these.pdf © [W. Fan], [2019], INSA Lyon, tous droits réservés - 2 - Cette thèse est accessible à l'adresse : http://theses.insa-lyon.fr/publication/2019LYSEI022/these.pdf © [W. Fan], [2019], INSA Lyon, tous droits réservés List of Abbreviations 2-MeTHF 2-Methyltetrahydrofuran 5-CMF 5-Chloromethylfurfural AIBN Azobisisobutyronitrile aq aqueous BHA Butylated hydroxyanisole Boc tert-Butoxycarbonyl bp Boling point CPME Cyclopentyl methyl ether CuAAC Copper-catalyzed alkyne-azide cycloaddition DABCO 1,4-Diazabicyclo[2.2.2]octane DAMF 2,5-Diaminomethylfuran DAST Diethylaminosulfur trifluoride DBU 1,8-Diazabicyclo[5.4.0]undec-7-ene DCC N,N'-dicyclohexylcarbodiimide DCE 1,2-Dichloroethane DCM Dichloromethane DDQ 2,3-Dichloro-5,6-dicyano-1,4-benzoquinone DHMF 2,5-Dihydroxymethylfurfural DHPM 3,4-Dihydropyrimidin-2(1H)-one DIAD Diisopropyl azodicarboxylate DIPEA Diisopropylethylamine DMAP N,N-4-dimethylaminopyridine DMF N,N-dimethylformamide - 3 - Cette thèse est accessible à l'adresse : http://theses.insa-lyon.fr/publication/2019LYSEI022/these.pdf © [W. Fan], [2019], INSA Lyon, tous droits réservés DMF 2,5-Dimethylfuran DMP Dess-Martin periodinane DMSO Dimethylsulfoxide DPPA Diphenylphosphoryl azide dr Diastereomeric ratio EMF 5-Ethoxymethylfurfural ESI Electrospray ionization FDCA 2,5-Furandicarboxylic acid GMF Glucosyloxymethylfurfural HCPN 3-Hydroxymethyl cyclopentanone HCPL 3-Hydroxymethylcyclopentanol HD 2,5-Hexanedione HFIP Hexafluoroisopropanol HHCPN 4-Hydroxy-4-(hydroxymethyl)cyclopent-2-en-1-one HHD 1-Hydroxy-2,5-hexanedione HLB Hydrophile-lipophile balance HMBC Heteronuclear multiple bond correlation HMF 5-Hydroxymethylfurfural HMFA 5-Hydroxymethyl furanoic acid HMVF 5-Hydroxymethyl-2-vinylfuran HOBt 1-Hydroxybenzotriazole HRMS High resolution mass spectroscopy HSQC
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