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Fluorophosphonium Chemistry: Applying Strategies Learned from Boron to Phosphorus

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Fluorophosphonium Chemistry: Applying Strategies Learned from Boron to Phosphorus Fluorophosphonium Chemistry: Applying Strategies Learned from Boron to Phosphorus by Shawn William Postle A thesis submitted in conformity with the requirements for the degree of Doctor of Philosophy Department of Chemistry University of Toronto Fluorophosphonium Chemistry: Applying Strategies Learned from Boron to Phosphorus Shawn William Postle Doctor of Philosophy Department of Chemistry University of Toronto Abstract Since the inception of frustrated Lewis pair chemistry, interest in main group catalysts has undergone a resurgence. Central to the success of many main group systems is the pentafluorophenyl substituent, which provides both chemical stability and electrophilicity to the catalyst. Pentafluorophenyl substituents have been used with boranes, alanes, and recently in fluorophosphonium cations. This thesis investigates a range of related aryl substituents applied to fluorophosphonium chemistry to elicit new catalyst properties. Nitrene insertion into the bonds of borane substituents, including perfluorophenyl groups, was used to tune the electrophilicity of main group systems. Sterically demanding pentachlorophenyl substituents were used to add protection to sensitive fluorophosphonium catalysts. Perfluorobiphenyl groups were used to generate more electrophilic fluorophosphonium catalysts. Binaphthyl substituents were employed to create chiral fluorophosphonium cations. ii This work is dedicated in memory of my grandpa, William Kerr, for instilling in me a genuine curiosity of the world. iii Acknowledgements First and foremost, I would like to thank Prof. Doug Stephan for providing me with this experience. By providing me with the freedom to pursue my own interests and offering insightful guidance whenever it was sought, you have helped me become a better chemist. I would like to thank my committee members, Prof. Bob Morris and Prof. Ulrich Fekl, for their enthusiasm and encouragement. I am grateful to Prof. Datong Song and my external examiner Prof. Chuck Macdonald for providing me with invaluable feedback. I am also extremely thankful to Dr. Barb Morra for her mentorship and collaboration. Additionally, I would like to thank my undergraduate supervisor Prof. Peter Legzdins for setting me upon this path. I have been incredibly fortunate to have worked alongside such a fantastic group of labmates, both past and present. I am grateful to Dr. Gab Menard for taking the time to get me situated in the lab. Vitali Podgorny, it was a pleasure to collaborate with you on our perchloroaryl chemistry. James LaFortune, I couldn’t ask for a better desk or gym partner. Tim Johnstone, you have been incredibly generous with your time and expertise, for which I am incredibly appreciative. I would also like to thank Julia Bayne, Louie Fan, James LaFortune, Eliar Mosaferi and Kevin Szkop for editing chapters of my thesis. I’m also indebted to our group’s fantastic evolving crystallography team over the years for providing me with some colour to break up the text herein. I am grateful to Darcy Burns, Sergiy Nokhrin, and Jack Sheng from the NMR department for fixing our spectrometer, helping me with difficult experiments, and fixing our spectrometer. I would like to thank Matthew Forbes, Fung Chung Woo, and Michelle Young of the AIMS lab for all their effort in finding just the right method for my compounds. I would like to thank Rose Balazs and the rest of the ANALEST staff for their expertise. I am also very appreciative of all the help John Ford of the Machine Shop has provided me over the years. I would like to thank Mom, Dad, Chris, and Michelle for all their unwavering love and continuous support. And finally, to my dearest Samantha, every day with you is a joy and you make me excited for everything yet to come. iv List of Abbreviations α alpha Å angstrom, 10-10 m AN Gutmann acceptor number atm. atmosphere β beta BCF B(C6F5), tris(pentafluorophenyl)borane br broad Bu butyl C Celsius cm centimeter C6D6 deuterated benzene C6F5 pentafluorophenyl C12F9 2-nonafluorobiphenyl C10H6 naphthyl C20H12 1,1’-binaphthyl calcd. calculated CH2Cl2 dichloromethane Cls SO2(4-ClC6H4), 4-chlorobenzenesufonyl COSY correlational spectroscopy δ delta, chemical shift v Δ Delta ° degrees d doublet, days -dn n-deuteron isotopologue DART direct analysis in real time DEPT distortionless enhancement by polarization transfer DFT density functional theory η eta, hapticity E energy eq. equivalent(s) eV electron volts ESI electrospray ionization Et ethyl Et2O diethyl ether FIA fluoride ion affinity FLP frustrated Lewis acid g gram GEI global electrophilicity index h hour HRMS high resolution mass spectrometry HMBC heteronuclear multiple bond correlation vi HOESY heteronuclear Overhauser effect spectroscopy HSQC heteronuclear single quantum coherence Hz Hertz iPr Isopropyl IR infrared n Jxy n-bond scalar coupling between nuclides x and y κ kappa, denticity K Kelvin kJ/mol kilojoules per mole μ mu, bridging, absorption coefficient m multiplet, meta Mes mesityl Me methyl mg milligram MHz megahertz mL milliliter mmol millimole MS mass spectrometry Ms SO2(CH3), methanesulfonyl NHC N-heterocyclic carbene NMR nuclear magnetic resonance vii Ns SO2(4-NO2C6H4), 4-nitrobenzenesufonyl ω omega, global electrophilicity index value o ortho - OTf (CF3SO3) , triflate anion π pi p para ppm parts-per-million, 10-6 pent. n-pentane POV-Ray Persistence of Vision Raytracer Ph phenyl q quartet quin. quintet RT room temperature σ sigma s singlet SCE saturated calomel electrode t triplet tBu tert-butyl THF tetrahydrofuran tol tolyl Ts SO2(4-(CH3)C6H4), 4-toluenesulfonyl viii Table of Contents Abstract ........................................................................................................................................... ii Acknowledgements ........................................................................................................................ iv List of Abbreviations ...................................................................................................................... v Table of Tables ............................................................................................................................ xiii Table of Schemes ......................................................................................................................... xiv Table of Figures .......................................................................................................................... xvii Chapter 1 Introduction .................................................................................................................... 1 1.1 Elemental Phosphorus ...................................................................................................... 1 1.2 Lewis Acidic Phosphorus Species .................................................................................... 2 1.2.1 Phosphenium Cations................................................................................................ 2 1.2.2 Phosphonium Cations ............................................................................................... 3 1.2.3 Fluorophosphonium Catalysts .................................................................................. 5 1.2.4 Dicationic Phosphorus Catalysts............................................................................... 9 1.3 Electrophilicity and Lewis Acidity Measurement Scales .............................................. 10 1.3.1 Chemical Shift Electrophilicity Scales ................................................................... 11 1.3.2 Computational Electrophilicity Measures............................................................... 14 1.4 Scope of Thesis .............................................................................................................. 16 1.5 References ...................................................................................................................... 18 Chapter 2 Nitrene Insertion into Boranes ..................................................................................... 23 2.1 Introduction .................................................................................................................... 23 2.1.1 Hypervalent Iodine Reagents .................................................................................. 23 2.1.2 Electrophilic Borane Reagents ................................................................................ 25 2.1.3 Frustrated Lewis Pair Chemistry ............................................................................ 27 2.1.4 Post-Synthetic Tuning Strategies ............................................................................ 28 ix 2.2 Results and Discussion ................................................................................................... 29 2.2.1 Synthesis and Characterization of Aminoboranes .................................................. 29 2.2.2 Electrophilicity of Aminoboranes ........................................................................... 39 2.2.3 Reactivity of Aminoboranes ................................................................................... 43 2.2.4 Mechanism of Nitrene Insertion ............................................................................. 45 2.2.5 Synthesis and Characterization of Phosphinimines ................................................ 46 2.3 Conclusion ...................................................................................................................... 50 2.4 Experimental .................................................................................................................
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