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Durham E-Theses Durham E-Theses Approaches to Novel B-N Chemistry at the Boundary of Frustrated Lewis Pairs and Bifunctional Catalysis ARKHIPENKO, SERGEY,YURIEVICH How to cite: ARKHIPENKO, SERGEY,YURIEVICH (2017) Approaches to Novel B-N Chemistry at the Boundary of Frustrated Lewis Pairs and Bifunctional Catalysis , Durham theses, Durham University. Available at Durham E-Theses Online: http://etheses.dur.ac.uk/12213/ Use policy The full-text may be used and/or reproduced, and given to third parties in any format or medium, without prior permission or charge, for personal research or study, educational, or not-for-prot purposes provided that: • a full bibliographic reference is made to the original source • a link is made to the metadata record in Durham E-Theses • the full-text is not changed in any way The full-text must not be sold in any format or medium without the formal permission of the copyright holders. Please consult the full Durham E-Theses policy for further details. Academic Support Oce, Durham University, University Oce, Old Elvet, Durham DH1 3HP e-mail: [email protected] Tel: +44 0191 334 6107 http://etheses.dur.ac.uk 2 Approaches to Novel B-N Chemistry at the Boundary of Frustrated Lewis Pairs and Bifunctional Catalysis Sergey Arkhipenko A thesis submitted in partial fulfilment of the requirements for the degree of Doctor of Philosophy Department of Chemistry, Durham University, UK 2016 Declaration The work described in this thesis was carried out in the Department of Chemistry at Durham University between October 2013 and December 2016, under the supervision of Prof. Andy Whiting. The material contained has not been previously submitted for a degree at this or any other university. The research reported within this thesis has been conducted by the author unless indicated otherwise. Statement of Copyright The copyright of this thesis rests with the author. No quotations from it should be published without prior consent and information derived from it should be acknowledged. 2 Contents I. Abstract ................................................................................................................. 5 II. Acknowledgements ........................................................................................... 6 III. Abbreviations .................................................................................................... 8 1. Introduction ........................................................................................................ 10 1.1. Frustrated Lewis Pairs ............................................................................... 11 1.1.1. The FLP concept .................................................................................. 11 1.1.2. Hydrogenations .................................................................................... 12 1.1.3. Other applications ............................................................................... 18 1.2. The Boundary between FLP and bifunctional catalysis.......................... 22 1.2.1. Separate Lewis acids and bases in comparison with FLP chemistry . ............................................................................................................... 22 1.2.2. “Frustration” and reactivity of Lewis pairs ...................................... 25 1.2.3. Reactivity of classic Lewis adducts (CLAs) ....................................... 26 1.2.4. Benefits of reducing Lewis acidity and basicity ................................ 29 1.2.5. Other approaches to avoid Lewis adduct formation ........................ 30 1.2.6. Importance of link between LA and LB centres ............................... 32 1.3. Conclusion ................................................................................................... 33 2. Results and discussion ....................................................................................... 34 2.1. Aims of the project ...................................................................................... 34 2.2. Part I. New bifunctional B-N catalysts...................................................... 34 2.2.1. Design and retrosynthetic analysis of new catalysts ......................... 34 2.2.2. Path A. Diaryl α-chloromethyl borane 110 approach ...................... 36 2.2.2.1. Borinate synthesis ......................................................................... 36 2.2.2.2. Borinate approach. Further steps ............................................... 43 2.2.2.3. Boron halides approach ............................................................... 47 2.2.2.4. Other approaches ......................................................................... 52 2.2.3. Paths B-C and hydroboration attempt .............................................. 54 2.2.4. Path D. Borylation with B2pin2 ........................................................... 56 2.2.4.1. Homoboroproline 114 synthesis .................................................. 56 2.2.4.2. Attempted derivatisation of homoboroproline 114 ................... 61 2.2.4.3. Attempted catalysis with homoboroproline derivative 176 ...... 65 3 2.2.5. NMR analysis of proline derivatives .................................................. 66 2.2.5.1. Analysis of diastereotopic protons and rotamers ...................... 67 2.2.5.2. 1H NMR resolution in prolinol 159 spectra ............................... 71 2.3. Part II. Direct amide formation ................................................................. 74 2.3.1. Non-catalysed, background thermal direct amide formation ......... 74 2.3.1.1. Amide formation: Flow reactor .................................................. 75 2.3.1.2. Amide formation: Microwave reactor........................................ 78 2.3.2. Boron-catalysed direct amide formation ........................................... 86 2.3.2.1. Interactions of borinic and boronic acids with amines ............. 86 2.3.2.2. Interactions of borinic and boronic acids with carboxylic acids . ........................................................................................................ 90 2.3.2.3. Interactions of borinic and boronic acids with carboxylic acids and amines ....................................................................................................... 98 2.3.2.4. Borinic and boronic acids in direct amide formation ............. 103 2.3.2.5. Boronic diamides ........................................................................ 107 2.3.2.6. Mechanistic conclusions on boronic acid catalysed direct amide formation ...................................................................................................... 111 2.4. Conclusions and future work ................................................................... 117 3. Experimental .................................................................................................... 119 3.1. General Information ................................................................................. 119 3.2. Synthetic procedures ................................................................................ 120 4. Appendix 1 ........................................................................................................ 142 5. Appendix 2 ........................................................................................................ 148 6. References. ........................................................................................................ 149 4 I. Abstract This project is devoted to boron chemistry in two ways. Firstly, the development of the boron – nitrogen “Frustrated” Lewis Pairs (FLPs) was investigated by combining the principles of this approach with known bifunctional catalytic methods. This also included design and synthetic efforts towards new bifunctional catalysts 108 and 157 on the basis of L-proline connected to Lewis acidic borane or borinic derivatives, which revealed multiple peculiarities of boron chemistry. Catalyst 176 was successfully utilised in nitro-Michael addition reaction. Secondly, boronic acids are promising catalysts for the important process of direct amide formation, which is a much more atom efficient and sustainable alternative to the current industrial approaches to amide synthesis. However, the mechanism of action of boronic acids in this process is not yet well understood, while this is crucial for effective design and future application of catalysts for direct amide formation. Thus the roles of both borinic and boronic acids in direct amide formation reactions were investigated. This included isolation of multiple Lewis adducts formed as intermediates or byproducts in different reaction mixtures between amines, carboxylic acids and boron-containing compounds. These results have helped to better understand the reactivity of boron-based catalysts and allowed development of the new mechanistic understanding of boronic acids in direct amide formation. These finding underlined the complexity of boron-containing systems, the importance of boron-nitrogen Lewis adduct interactions and the high possibility of multiple boron atoms orchestrating the investigated processes. The non-catalytic thermal direct amide formation reaction was also studied both in flow and microwave reactors in order to better understand these complex multicomponent systems. 5 II. Acknowledgements First of all, I would like to thank my supervisor, Prof. Andy Whiting, who gave me a brilliant opportunity to work in his group in UK. Apart from owning outstanding knowledge of chemistry and passion for
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