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Gold(I) Catalysis Under Visible Light Zhonghua Xia

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Gold(I) Catalysis Under Visible Light Zhonghua Xia Gold(I) Catalysis Under Visible Light Zhonghua Xia To cite this version: Zhonghua Xia. Gold(I) Catalysis Under Visible Light. Organic chemistry. Sorbonne Université, 2018. English. NNT : 2018SORUS606. tel-02954132 HAL Id: tel-02954132 https://tel.archives-ouvertes.fr/tel-02954132 Submitted on 30 Sep 2020 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. Sorbonne Université Ecole Doctorale de Chimie Moléculaire de Paris Centre Institut Parisien de Chimie Moléculaire / Equipe Méthodes et Applications en Chimie Organique Gold(I) Catalysis Under Visible Light Par Zhonghua XIA Thèse de doctorat de Chimie Organique Dirigée par Prof. Louis FENSTERBANK, Dr. Virginie MOURIES-MANSUY et Dr. Cyril OLLIVIER Présentée et soutenue publiquement le 19 octobre 2018 Devant un jury composé de : M. Igor ALABUGIN Professeur, Florida State University, USA Rapporteur M. Abderrahmane AMGOUNE Professeur, Université Claude Bernard Lyon 1 Rapporteur M. Philippe BELMONT Professeur, Université Paris Descartes Examinateur M. Matthieu SOLLOGOUB Professeur, Sorbonne Université Examinateur M. Louis FENSTERBANK Professeur, Sorbonne Université Directeur de thèse Mme Virginie MOURIÈS-MANSUY Maître de conférence-HDR, Sorbonne Université Directeur de thèse Sorbonne Université Ecole Doctorale de Chimie Moléculaire de Paris Centre Institut Parisien de Chimie Moléculaire / Equipe Méthodes et Applications en Chimie Organique Gold(I) Catalysis Under Visible Light Par Zhonghua XIA Thèse de doctorat de Chimie Organique Dirigée par Prof. Louis FENSTERBANK, Dr. Virginie MOURIES-MANSUY et Dr. Cyril OLLIVIER Présentée et soutenue publiquement le 19 octobre 2018 Devant un jury composé de : M. Igor ALABUGIN Professeur, Florida State University, USA Rapporteur M. Abderrahmane AMGOUNE Professeur, Université Claude Bernard Lyon 1 Rapporteur M. Philippe BELMONT Professeur, Université Paris Descartes Examinateur M. Matthieu SOLLOGOUB Professeur, Sorbonne Université Examinateur M. Louis FENSTERBANK Professeur, Sorbonne Université Directeur de thèse Mme Virginie MOURIÈS-MANSUY Maître de conférence-HDR, Sorbonne Université Directeur de thèse Si vous avez la chance d'avoir vécu jeune homme à Paris, où que vous alliez pour le reste de votre vie, cela ne vous quitte pas, car Paris est une fête. ― Ernest Hemingway If you are lucky enough to have lived in Paris as a young man, then wherever you go for the rest of your life, it stays with you, for Paris is a moveable feast. ― Ernest Hemingway 假如你有幸年轻时在巴黎生活过，那么你此后一生中不论去到哪里，她都与你同在， 因为巴黎是一席流动的盛宴。— 欧内斯特·海明威 To me, Follow your heart. Acknowledgments This work was carried out from October 2015 to October 2018 under the guidance of Prof. Louis Fensterbank, Dr. Virginie Mouriès-Mansuy and Dr. Cyril Ollivier in the laboratory “Méthodes et Applications en Chimie Organique (MACO)” at Institut Parisien de Chimie Moléculaire (IPCM), Sorbonne Université and involved many people to whom I would like to express my deep gratitude. First of all, I warmly thank the mem ers of the jury for accepting to e the reviewers of this thesis: Prof Igor Ala ugin from lorida State University Tallahassee USA Prof A derrahmane Amgoune from Université Claude ernard - Lyon 1, Prof. Philippe elmont from Université Paris escartes Prof Matthieu Sollogou from Sor onne Université Your invaluable comments and suggestions would help me improve the quality of this thesis. I want to express many thanks to my supervisor, Prof. Louis Fensterbank, who gives me an opportunity to pursue my Ph.D. study in MACO group and for his kind attention and excellent guidance throughout the past three years of my study and research. On the way to pursue science, we have many discussions, sometimes different opinions, it promotes us thinking a question more comprehensive and deeper, and I think that is research and chemistry. He has a wide knowledge, works efficient and hard. This three-year study life was accompanied by his candid discussion, pertinent criticism, constant encouragement, and unexpected humor. He taught me many things, like how to do research and to be a chemist, balance thinking and doing, working and playing. Moreover, we are 2018 Paris Marathon finishers in MACO group, I will be always proud of it. I am truly grateful to Dr. Virginie Mouriès-Mansuy, my co-advisor, and the gold chemist, for her guidance and supports in my experiments. She is always ready for providing help and solving problems very quickly, I have to work very efficiently to follow her step. I would thank her patience teaching for experimental techniques and correction for the French summary of my thesis. I really appreciate her humor and cheer me up, especially when my reaction did not work very well, her encouragement motivates me a lot to achieve the goal. I want to thanks Dr. Cyril Ollivier, my co-advisor, also the chef of photocatalysis and seminar. He has a wide knowledge of radical chemistry and photocatalysis, which provides me with very useful guidance and advice. I appreciate a lot the mechanism discussion with him, he always provides professional opinions about my questions. Also, his mildness and optimism always bring my peace and full of energy. 1 My appreciation is also given to people who participate in my projects. I want to thanks Dr. Vincent Corcé, who participate in my second project and helped me to do the fluorescence quenching experiments and cyclic voltammetry experiments. Thanks for his work on my project and correction of the supporting information. Dr. Yves Gimbert and Dr. Héloïse Dossmann carried out the computational studies, it‟s significant for the mechanism explanation, and Jérémy Forté is acknowledged for the XRD analyses. I am grateful to Omar Khaled for HRMS and Cédric Przybylski for the MS analyses. I also want to thanks Dr. Bastien Nay and Frederic De Montigny, who are my committees in “comité de suivi” for their suggestions to my research. And Natalia Del Rio, the nice and optimistic Spanish girl, who worked neighbor to my bench for one year, I appreciate our talk about chemistry and weekend. She has skilled experiment techniques and wide chemistry knowledge, gave me much useful advice. Thanks to Alejandro, my Mexico friend who worked with me in the same office in my first year. Thanks for his advice in my chemistry and help me adopt the new life in a new group. Many thanks to Avassaya Vanitcha, the nice and friendly Thailand girl, for her help in my first experiment, it‟s essential for me to adopt a new lab. Thanks! I would like to say thanks to the MACO team. Dr. Corinne Aubert, who is the former director of IPCM, the Dean of the Faculty of Science and Engineering now, for her kindness; Dr. Gilles Lemière, who worked with me in the same lab, I appreciate his help and joke in the lab; Dr. Marc Petit for his security work in the Lab; Dr. Marion B. for her kindness; Dr. Marine for her cheering up; Dr. Muriel for her kindness and organization of group party. I also say merci to all my current and former colleagues in the MACO team. Thanks to Anthony, the friendly and strong guy, I fell very lucky we are same year Ph.D. students, every time talking with him makes me peaceful and pleasant, his hardworking and optimistic always motivate me. Yes, I like beer too. Thanks to Laura H., the nice girl who can speak very fluent English. Thanks for her help when I have French language questions. Thanks to Christophe, the cool and responsible guy, I still remembered how he taught me to synthesize the Iridium photocatalyst, I followed his procedure and tips, and success for one time. Great! Valérie (Vava) for her kindness and friendliness, who can speak many languages, French, English, Spanish, Chinese, Japanese, and maybe more…She can speak many Chinese words now, even sing a song, Tian Mimi. Caleb for his friendliness and funny. Laura F. for her kindness and organization of group drinking, the after-work party in Champs-Élysées is impressing me even now; Jéremy for his kindness and fantastic humor; Maud for her funny and organization of group lunch. Thanks Nicola, the young America high school student, who can speak fluent 2 Chinese, also like Chinese food and culture very much. Amazing! Thanks to Francesco, the nice Italy practice student, I hope he can be a good chemist in the future. And thanks Julien, Simon, Ludwig, Fabrizio, Cédric, Etienne, Thibaut, rédéric … I would like to thank Prof. Yongmin Zhang, for his kind concern to my study and life in the last three years. It‟s always very pleasant to talk to him, every time our talk makes me think more clearly about my situation and future. Thanks to my Chinese friends, Xiaolei, Yang, Jingwen and Teng, we can talk about everything in our lunchtime, we share happiness and sadness, I fell so luckily I have your friends! Also, I want to thanks to my junior Chinese colleagues, Yufeng, Ye, Fen, and Hengrui, they bring me happiness and company, it is invaluable! Finally, I want to thanks my family, their love and support always make me happy and successful in my life. I love Paris! Zhonghua Xia Sept 17, 2018, Paris 3 4 Contents Acknowledgments ....................................................................................................................
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