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Investigating Benign Syntheses Via Mechanochemistry Investigating benign syntheses via mechanochemistry A dissertation submitted to the Graduate School of the University of Cincinnati in partial fulfillment of the requirements for the degree of DOCTOR OF PHILOSOPHY (Ph.D.) in the Department of Chemistry of the College of Arts and Sciences 2020 Lianna N Ortiz-Trankina B.S., Shawnee State University, 2015 Committee Chair: James Mack, Ph.D. Abstract In the last few decades, a larger effort has been given toward the development of more environmentally benign and human friendly processes and environments. This dissertation focuses on the use of a high-speed ball mill as a technique for solvent-free and benign mechanochemical synthesis. In order to minimize solvent waste production and the use of hazardous reagents, my research focused on developing safer synthetic routes with the use of benign reagents. There is also a large focus on the interaction and coordination of ions in solid state synthesis and how the lack of solvent can aid with the chemo- and stereoselectivity of these reactions. This work also demonstrates how the mechanochemical nature of these reactions can aid in the overcoming of the activation barrier in specific reactions. This approach is believed to be an environmentally friendly technique to understanding the foundations of many organic synthetic reactions. ii iii Acknowledgements There are many people who deserve to be recognized in this section, but first I would like to thank my best friend and partner in life Jared. Thank you for supporting me and pushing me to continue through graduate school when I had doubted myself so many times. Thanks for heeding (take heed of?) my rants, soaking up all the tears, and listening to all my talks. Your endless love, support and encouragement have made this journey endurable. I would also like to thank Audrey, Jared, and Sean for their hospitality, friendship, and encouragement to go to graduate school. Along with them, I would like to thank the rest of my former SSC family, especially Deanna, Michelle, Amanda, and Debbie, for their help and support. I honestly believe I would not be where I am today without all their generosity. I would like to thank my chemistry professors at Shawnee State, especially Dr. Derek Jones for giving me the opportunity to perform undergraduate research and encouraging me to go to graduate school. The friends I have made in Cincinnati also deserve recognition. I especially would like to thank Gurdat. Our taco and margarita dates were a constant highlight through this adventure, and I will never forget San Diego. I would also love to thank Melissa. You have been an amazing friend and our Starbucks coffee runs were always the perfect break. I would like to thank the members of the Mack group for all their help, advice, and encouragement. Thank you, Dr. Mack, for supporting my endeavors and for your mentorship. Your guidance has shaped the way I approach problem solving and mentoring. Heather, Kendra and Becca, thank you for being great friends and mentors even post-graduation. Thank you, Joel and Cong, for all your help, conversations and expertise. Thank you also to the members I am leaving behind: iv Jazmine, Niza, Menna, and Rohesh. While I am excited for the future, I will miss our daily (pre- COVID-19) conversations and laughs. Also, thank you to Jessie. I am so glad you came with us to the Green Chemistry Conference and winning our first The Office trivia with you and Becca is still one of the biggest highlights of my life. I would also like to thank my e-friends Jamie, Mark, and Nicole. Our daily random conversations are always a highlight. I want to thank you guys for your openness and acceptance. We are all different types of people, yet we click so well as friends and I appreciate your love and encouragement. Lastly, I would like to thank my parents. I hope someday you stumble upon this and know that I appreciate all that you have done for me. My work ethic, critical thinking, and communication skills all stem from the lessons you taught me throughout the years. I still have that torn piece of notebook paper where “Dr. Lianna Nina Ortiz-Trankina, MD or PhD” was written out. You knew what I was capable of and you encouraged me to always work hard so I could reach my fullest potential. Thank you to those who provided funding in support of my research, education, and salary during my time in graduate school; namely, the National Science Foundation, the American Chemical Society and the University of Cincinnati Department of Chemistry. v Table of Contents Abstract .................................................................................................................................. ii Acknowledgments ................................................................................................................. iv Table of Contents .................................................................................................................. vi List of Figures ....................................................................................................................... viii List of Symbols ..................................................................................................................... xiii Chapter 1. Introduction ........................................................................................................... 1 Mechanochemistry .................................................................................................................. 2 Ball milling ............................................................................................................................... 3 Ions and solvent ....................................................................................................................... 6 Hard-soft acid-base theory ....................................................................................................... 8 References ............................................................................................................................. 12 Chapter 2.Ion Pair Roles in Acid/Base and Nucleophilic Substitution Reactions ................... 14 Introduction ........................................................................................................................... 14 Results and Discussion ........................................................................................................... 19 Phenol Williamson Ether Synthesis ............................................................................. 19 Electrophilic aromatic substitution production ........................................................... 22 Benzyl alcohol Williamson Ether Synthesis ................................................................. 25 4-bromobenzyl iodide degradation ............................................................................. 29 EcoScale ..................................................................................................................... 32 Conclusions ............................................................................................................................ 35 Experimental .......................................................................................................................... 37 References ............................................................................................................................. 40 Chapter 3. Ion Pair Regioselectivity and Stereoselectivity .................................................... 41 Introduction ........................................................................................................................... 41 Results and Discussion ........................................................................................................... 42 Ion pair regioselectivity .............................................................................................. 42 vi Ion pair stereoselectivity ............................................................................................ 47 Conclusions ............................................................................................................................ 51 Experimental .......................................................................................................................... 52 References ............................................................................................................................. 54 Chapter 4. Benign Alkyne Chemistry ..................................................................................... 56 Introduction ........................................................................................................................... 56 Results and Discussion ........................................................................................................... 58 Nucleophilic Substitution ............................................................................................ 58 Nucleophilic Addition ................................................................................................. 62 Enyne Formation ........................................................................................................ 65 Hydrations .................................................................................................................. 66 Conclusions ........................................................................................................................... 72 Experimental .........................................................................................................................
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