Title Studies on Catalytic Transformation of Aldehydes via η^2-Coordination to Nickel(0) PDF
Preview Title Studies on Catalytic Transformation of Aldehydes via η^2-Coordination to Nickel(0)
Studies on Catalytic Transformation of Title Aldehydes via η^2-Coordination to Nickel(0) Author(s) Hoshimoto, Yoichi Citation Issue Date oaire:version VoR URL https://hdl.handle.net/11094/27542 rights Note OOssaakkaa UUnniivveerrssiittyy KKnnoowwlleeddggee AArrcchhiivvee :: OOUUKKAA https://ir.library.osaka-u.ac.jp/ Osaka University tY t63b7 Doctoral Dissertation of Studies on Catalytic Transformation Aldehydes viaゲロCoordination to Nickel(0) Yoichi Hoshil■oto January 2013 Graduate School of Engineering Osaka University Doctoral Dissertation Studies on Catalytic Transformation of Aldehydes viaゲ ‐C00rdination tO Nickel(0) Yoichi Hoshilnoto January 2013 Graduate School of Engineering Osaka University Preface and Acknowledgements The study in this thesis has been carried out under the direction of Professor Sensuke Ogoshi at the Department of Applied Chemistry Faculty of Engineering, Osaka University from April 2003 to March 2013. The thesis describes the catalytic transformation of aldehydes via r1'-cootdination to nickel(0). For accomplishment of my works, there were really lots of helps, advices, and supports. I owe all of them a great debt of gratitude; however, I regret to say that I cannot all ofthem here. I wish to express my greatest gratitude to Professor Sensuke Ogoshi (BOSS) for a great number of suggestions, discussions, and encouragements (he often said to me iOgftnut!"). He was really strict about chemistry and always gave me logical directions. In addition, his enthusiasm for chemistry always filled me with a feeling of respect. I would like to express my appreciation to Professor Nobuaki Kambe and Professor Naoto Chatani for their stimulating discussions. I would like to give my special thanks to Professor Tetsuro Murahashi at Institute for Molecular Science and Assistant Professor Masato Ohashi for their valuable and productive advices. They taught me an importance of perseverance. I deeply thank Ms. Noriko Fujimoto for her everyday lovely smile, and heart-warming encouragements. My especially thanks go as well to the past and present members in the Ogoshi Group. When I joined the group in April 2007 as a bachelor student, many talented seniors, Dr. Yasuki Tatsumi (a tenible but respectful drinker), Mr. Katsunori Shirato, Mr. Yoshinori Ohe, Mr. Masahiro Ikawa (he always encouraged me), Mr. Ryo Inoue, Dr. Takashi Tamaki (very respectful senior in my Ph.D student course), gave me lots of advices about experimental know-how. As colleagues for the master's course, Mr. Osamu Kishizaki, Mr. Koji Chiyoda, Mr. Toshifumi Haba, and Ms. Adusa Fukushima always helped my laboratory's life. I am much obliged to all of my juniors in the Ogoshi Group, Mr. Tadashi Kambar4 Mr. Tomoaki Taniguchi, Mr. AkiraNishimura, Mr. Kentaro Usui, Mr. Hiroki Saijyo, Mr. Ippei Takeda, Mr. Kohe Takase, Ms. Haruka Suzuki (she worked with me for 3 years, and showed me a lot of surprising and intriguing results), Mr. Ryohei Doi, Mr. Ryohei Kamura, Mr. Yuki Tachibana, Mr. Hiromu Tokura, Mr. Tomoya Ohata, Mr. Seita Kimura, Mr. Mitsutoshi Shibata, Ms. Yukari Hayashi (she worked quite hard and helped me for 2 years), Mr. Hiroaki Saito, Mr. Hironobu Sakaguchi, Ms. Eri Tamai, and Mr. Hayato Yabuki (he worked with me since September 2012, and studied vigorously) for their kind dedications. I would like to thank Dr. Nobuko Kanehisa for her helpful assistance for X-ray crystallographic analysis. Thanks are also due to the Instrumental Analysis Center, Graduate School of Engineering, Osaka University, for the measurement of spectral and analytical data. I acknowledge the Research Fellowship from the Japan Society for the Promotion of Science for Young Scientists (April 2010-May 2013) and the Global COE Program "Global Education and Research Center for Bio-Environmetal Chemistrv" of Osaka University. Finally, my utmost gratitude is dedicated to my mother, Mr. Hatsuko Hoshimoto, and all of my relatives in Nagano, for their understanding and encouragements. January 2013 Yoichi Hoshiinoto Contents I Chapter General Introduction Chapter 2 Ni(O)-Catalyzed lntramolecular Hydroacylation via 9 ry2-Rldehyde)( 72-Alkene)Nickel(0) Intermediate 1 Chapter 3 of Aldehydes via Ni(0)-catalyzed Homo-Dimeization 39 nis( ry2-Aldehyde)Nickel(0) Intermediate Chapter 4 Ni(0)-Catalyzed Crossed Tishchenko Reaction of Aliphatic Aldehydes with 53 Aromatic Aldehydes Chapter 5 Intramolecular Electrophilic Addition of Arylsilanes to (r7 -1{dehyde)Ni(0) 83 Complex ９７ Conclusion ９９ List of Publications Abbreviations The following abbreviations are used in the thesis. anal. Elemental anaylsys Ac acetyl aq. aqueous Ar aryl br broad Bn benzyl Bu butyl cat. catalyst Cf confer CI chemical ionization COd 1,5-cyclooctadiene Cy cyclohexyl C temperature in degrees centigrade d doublet δ chemical shift ofNMR signal in ppm EI electron ionization eq. equation equlv equivalent Et ethyl Et20 diethylether GC gas chromatography h hour(s) Hex hexyl HMBC hetero-nuclear multiple-bond connectivity HMQC hetero-nuclear multiple quantum coherence HPLC high-perfonnance liquid chromatography HRPIS hi gh-resolution mass specra Hz hertz J iso IR infrared spectroscopy 」 coupling constant in NMR KIE kinetic isotope effect L ligand M metal meta “NIle methyl nlln minute(s) mL milliliter μL microliter MS mass spectral 4 normal NHC l/-heterocyclic carbene NMR nuclear magnetic resonance lV ο ortho 側ＥＰ Oak Ridge therlnal ellipsoid p16t ′ para Ｐｈ phenyl Ｐｒ propyl ＰＲ３ trialkyl― or triaryl―phosphine q quartet quant quantitative ref refcrence RT room temperature S singlet sept septet sext sextet t triplet Tf trinuoromethylsulfonyl THF tetrahydrottan TMS trimethylsilyl t triplet Vl I Chapter General Introduction
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