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Fedor Mikhailovich NEW TRANSFORMATIONS BASED ON ACTIVATION OF INERT CARBON- HALOGEN BONDS WITH AND WITHOUT TRANSITION Miloserdov Fedor Mikhailovich Dipòsit Legal: T 825-2015 ADVERTIMENT. L'accés als continguts d'aquesta tesi doctoral i la seva utilització ha de respectar els drets de la persona autora. Pot ser utilitzada per a consulta o estudi personal, així com en activitats o materials d'investigació i docència en els termes establerts a l'art. 32 del Text Refós de la Llei de Propietat Intel·lectual (RDL 1/1996). Per altres utilitzacions es requereix l'autorització prèvia i expressa de la persona autora. En qualsevol cas, en la utilització dels seus continguts caldrà indicar de forma clara el nom i cognoms de la persona autora i el títol de la tesi doctoral. No s'autoritza la seva reproducció o altres formes d'explotació efectuades amb finalitats de lucre ni la seva comunicació pública des d'un lloc aliè al servei TDX. Tampoc s'autoritza la presentació del seu contingut en una finestra o marc aliè a TDX (framing). Aquesta reserva de drets afecta tant als continguts de la tesi com als seus resums i índexs. ADVERTENCIA. El acceso a los contenidos de esta tesis doctoral y su utilización debe respetar los derechos de la persona autora. Puede ser utilizada para consulta o estudio personal, así como en actividades o materiales de investigación y docencia en los términos establecidos en el art. 32 del Texto Refundido de la Ley de Propiedad Intelectual (RDL 1/1996). Para otros usos se requiere la autorización previa y expresa de la persona autora. En cualquier caso, en la utilización de sus contenidos se deberá indicar de forma clara el nombre y apellidos de la persona autora y el título de la tesis doctoral. No se autoriza su reproducción u otras formas de explotación efectuadas con fines lucrativos ni su comunicación pública desde un sitio ajeno al servicio TDR. Tampoco se autoriza la presentación de su contenido en una ventana o marco ajeno a TDR (framing). Esta reserva de derechos afecta tanto al contenido de la tesis como a sus resúmenes e índices. WARNING. Access to the contents of this doctoral thesis and its use must respect the rights of the author. It can be used for reference or private study, as well as research and learning activities or materials in the terms established by the 32nd article of the Spanish Consolidated Copyright Act (RDL 1/1996). Express and previous authorization of the author is required for any other uses. In any case, when using its content, full name of the author and title of the thesis must be clearly indicated. Reproduction or other forms of for profit use or public communication from outside TDX service is not allowed. Presentation of its content in a window or frame external to TDX (framing) is not authorized either. These rights affect both the content of the thesis and its abstracts and indexes. UNIVERSITAT ROVIRA I VIRGILI NEW TRANSFORMATIONS BASED ON ACTIVATION OF INERT CARBON-HALOGEN BONDS WITH AND WITHOUT TRANSITION Miloserdov Fedor Mikhailovich Dipòsit Legal: T 825-2015 DOCTORAL THESIS New Transformations Based on Activation of Inert Carbon-Halogen Bonds with and without Transition Metals Fedor M. Miloserdov Rovira i Virgili University Institute of Chemical Research of Catalonia UNIVERSITAT ROVIRA I VIRGILI NEW TRANSFORMATIONS BASED ON ACTIVATION OF INERT CARBON-HALOGEN BONDS WITH AND WITHOUT TRANSITION Miloserdov Fedor Mikhailovich Dipòsit Legal: T 825-2015 UNIVERSITAT ROVIRA I VIRGILI NEW TRANSFORMATIONS BASED ON ACTIVATION OF INERT CARBON-HALOGEN BONDS WITH AND WITHOUT TRANSITION Miloserdov Fedor Mikhailovich Dipòsit Legal: T 825-2015 UNIVERSITAT ROVIRA I VIRGILI NEW TRANSFORMATIONS BASED ON ACTIVATION OF INERT CARBON-HALOGEN BONDS WITH AND WITHOUT TRANSITION Miloserdov Fedor Mikhailovich Dipòsit Legal: T 825-2015 UNIVERSITAT ROVIRA I VIRGILI NEW TRANSFORMATIONS BASED ON ACTIVATION OF INERT CARBON-HALOGEN BONDS WITH AND WITHOUT TRANSITION Miloserdov Fedor Mikhailovich Dipòsit Legal: T 825-2015 Fedor M. Miloserdov New T ransformations Based on Activation of Inert Carbon-Halogen Bonds with and without T ransition Metals DOCTORAL THESIS Supervised by Dr. Vladimir V. Grushin Institut Català d'Investigació Química (ICIQ) Tarragona 2015 UNIVERSITAT ROVIRA I VIRGILI NEW TRANSFORMATIONS BASED ON ACTIVATION OF INERT CARBON-HALOGEN BONDS WITH AND WITHOUT TRANSITION Miloserdov Fedor Mikhailovich Dipòsit Legal: T 825-2015 UNIVERSITAT ROVIRA I VIRGILI NEW TRANSFORMATIONS BASED ON ACTIVATION OF INERT CARBON-HALOGEN BONDS WITH AND WITHOUT TRANSITION Miloserdov Fedor Mikhailovich Dipòsit Legal: T 825-2015 UNIVERSITAT INSTITUT CATALÀ ROVIRA I VIRGILI D'INVESTIGACIÓ DEPARTAMENT DE QUÍMICA (ICIQ) QUIMICA ANALITICA I QUIMICA ORGANICA C/ Marcel.lí Domingo s/n Av Països Catalans 16 Campus Sescelades 43007 Tarragona 43007 Tarragona Tel. 34 977 92 08 24 Tel. 34 977 55 97 69 Fax 34 977 92 08 25 Fax 34 977 55 84 46 e-mail: [email protected]. e-mail: [email protected] ,67$7(WKDWWKHSUHVHQWVWXG\HQWLWOHG³1HZ Transformations Based on Activation of Inert Carbon-+DORJHQ%RQGVZLWKDQGZLWKRXW7UDQVLWLRQ0HWDOV´SUHVHQWHGE\)HGRU M. Miloserdov for the award of the degree of Doctor, has been carried out under my supervision at the Institute of Chemical Research of Catalonia (ICIQ). Tarragona, 9 January 2015 Doctoral Thesis Supervisor Vladimir V. Grushin, PhD UNIVERSITAT ROVIRA I VIRGILI NEW TRANSFORMATIONS BASED ON ACTIVATION OF INERT CARBON-HALOGEN BONDS WITH AND WITHOUT TRANSITION Miloserdov Fedor Mikhailovich Dipòsit Legal: T 825-2015 UNIVERSITAT ROVIRA I VIRGILI NEW TRANSFORMATIONS BASED ON ACTIVATION OF INERT CARBON-HALOGEN BONDS WITH AND WITHOUT TRANSITION Miloserdov Fedor Mikhailovich Dipòsit Legal: T 825-2015 Dedicated to my Grandfather Fedor E. Miloserdov and Great-Grandmother Alexandra I. Kalinina UNIVERSITAT ROVIRA I VIRGILI NEW TRANSFORMATIONS BASED ON ACTIVATION OF INERT CARBON-HALOGEN BONDS WITH AND WITHOUT TRANSITION Miloserdov Fedor Mikhailovich Dipòsit Legal: T 825-2015 UNIVERSITAT ROVIRA I VIRGILI NEW TRANSFORMATIONS BASED ON ACTIVATION OF INERT CARBON-HALOGEN BONDS WITH AND WITHOUT TRANSITION Miloserdov Fedor Mikhailovich Dipòsit Legal: T 825-2015 First and foremost, I would like to express my deepest gratitude to my thesis supervisor Prof. Vladimir Grushin for the opportunity to perform my M.Sc. and Ph.D. studies in his research group. Through Prof. Grushin I gained the priceless chemical knowledge and experience to succeed in my studies, but more importantly the inspiration he gave me by showing how interesting and exciting scientific research can be. His unique guidance with strong leadership but also understanding and mutual respect encouraged me to do better. Finally I would like to personally thank Prof. Grushin for many valued chemistry and life lessons learned from him during my studies. I want to thank my former teachers and supervisors, especially Galina V. Farina, Olga V. Plugatarenko, Maria B. Postnikova, Sergey E. Semenov, Dmitrii M. Roitershtein, Alexander S. Dorofeev, and Ilya Yu. Titov. I am grateful to the ICIQ research and administrative staff for all their help and cooperation during my research work. My special thanks go to Noemí Panadès Muñoz for her tremendous help with administrative issues and to Drs. Jordi Benet-Buchholz, Eddy Martin, Marta Martínez Belmonte and Eduardo C. Escudero-Adán for numerous crystallographic studies. I also thank Germán Gómez and Israel Macho for their assistance with NMR experiments. I would like to express my appreciation to all former and current members of the Grushin research group, especially Andrey Konovalov, Liubov Panferova, Drs. Anton Lishchynskyi, Hamidreza Samouei, Noel Nebra, Alexander Ushkov, Olesya Tomashenko, Alessandro Zanardi, Prof. Shin Takemoto, Juan del Pozo, and Maksim Novikov for their assistance in the laboratory and interesting discussions. I am thankful to all of my lab mates and friends Masha Kirillova, Tameem Bader, Dina Fakhrnasova, Sanaz Mazloomi, Jhenia Gorbacheva and Andrew Romine for making my stay in Tarragona such an enjoyable experience. UNIVERSITAT ROVIRA I VIRGILI NEW TRANSFORMATIONS BASED ON ACTIVATION OF INERT CARBON-HALOGEN BONDS WITH AND WITHOUT TRANSITION Miloserdov Fedor Mikhailovich Dipòsit Legal: T 825-2015 I thank Dr. Claire L. McMullin, Dr. David McKay, and Prof. Stuart A. Macgregor of Heriot-Watt University for computational studies and for fruitful collaboration. It is a pleasure to acknowledge Drs. Hamidreza Samouei and Bianca K. Muñoz for their preliminary work that was essential for my studies described in Chapter 2 of this Thesis. I thank Prof. Vladimir I. Bakhmutov for many helpful discussions. The ICIQ foundation and the Spanish Ministry of Economy and Competitiveness (MINECO) are gratefully acknowledged for their financial support and for the FPI Ph.D. fellowship (BES-2012-054922). Last but not least, I thank my family, especially my father, mother, and brother for all their love, encouragement, and support (even at a distance). UNIVERSITAT ROVIRA I VIRGILI NEW TRANSFORMATIONS BASED ON ACTIVATION OF INERT CARBON-HALOGEN BONDS WITH AND WITHOUT TRANSITION Miloserdov Fedor Mikhailovich Dipòsit Legal: T 825-2015 $WWKHSULQWLQJRIWKLVPDQXVFULSWWKHUHVXOWVSUHVHQWHGKHUHLQKDYHEHHQSXEOLVKHGLQ x 3DOODGLXP-&DWDO\]HG$URPDWLF$]LGRFDUERQ\ODWLRQ )00LORVHUGRY99*UXVKLQ$QJHZ&KHP,QW(G x 7KH &KDOOHQJH RI 3DOODGLXP-&DWDO\]HG $URPDWLF $]LGRFDUERQ\ODWLRQ )URP 0HFKDQLVWLFDQG&DWDO\VW'HDFWLYDWLRQ6WXGLHVWRD+LJKO\(IILFLHQW3URFHVV ) 0 0LORVHUGRY & / 0F0XOOLQ 0 0DUWÕғQH] %HOPRQWH - %HQHW-%XFKKRO] 9,%DNKPXWRY6$0DFJUHJRU99*UXVKLQ2UJDQRPHWDOOLFV x $OFRKRO\VLVRIIOXRURIRUP
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