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Developing the Catalytic Asymmetric Hydroarsination Reaction This document is downloaded from DR‑NTU (https://dr.ntu.edu.sg) Nanyang Technological University, Singapore. Developing the catalytic asymmetric hydroarsination reaction Tay, Wee Shan 2020 Tay, W. S (2020). Developing the catalytic asymmetric hydroarsination reaction. Doctoral thesis, Nanyang Technological University, Singapore. https://hdl.handle.net/10356/142898 https://doi.org/10.32657/10356/142898 This work is licensed under a Creative Commons Attribution‑NonCommercial 4.0 International License (CC BY‑NC 4.0). Downloaded on 11 Oct 2021 05:24:27 SGT DEVELOPING THE CATALYTIC ASYMMETRIC HYDROARSINATION REACTION TAY WEE SHAN SCHOOL OF PHYSICAL AND MATHEMATICAL SCIENCES 2020 DEVELOPING THE CATALYTIC ASYMMETRIC HYDROARSINATION REACTION TAY WEE SHAN SCHOOL OF PHYSICAL AND MATHEMATICAL SCIENCES A thesis submitted to the Nanyang Technological University in partial fulfilment of the requirement for the degree of Doctor of Philosophy 2020 Statement of Originality I hereby certify that the work embodied in this thesis is the result of original research done by me except where otherwise stated in this thesis. The thesis work has not been submitted for a degree or professional qualification to any other university or institution. I declare that this thesis is written by myself and is free of plagiarism and of sufficient grammatical clarity to be examined. I confirm that the investigations were conducted in accord with the ethics policies and integrity standards of Nanyang Technological University and that the research data are presented honestly and without prejudice. 7 July 2020 . Date Tay Wee Shan Supervisor Declaration Statement I have reviewed the content and presentation style of this thesis and declare it of sufficient grammatical clarity to be examined. To the best of my knowledge, the thesis is free of plagiarism and the research and writing are those of the candidate’s except as acknowledged in the Author Attribution Statement. I confirm that the investigations were conducted in accord with the ethics policies and integrity standards of Nanyang Technological University and that the research data are presented honestly and without prejudice. 7 July 2020 . Date Leung Pak Hing 7 July 2020 . Date Sumod A. Pullarkat Authorship Attribution Statement This thesis contains material from seven paper(s) published in the following peer- reviewed journals where I was the first author. Chapter 1 is published as Tay, W. S.; Pullarkat, S. A. C–As Bond Formation Reactions for the Preparation of Organoarsenic(III) Compounds. Chem. Asian. J. 2020. DOI: 10.1002/asia.202000606. The contributions of the co-authors are as follows: • Dr Pullarkat, S. A. revised the manuscript draft, • I identified the area for review and gathered the relevant literature, and • I conducted the literature review and prepared the manuscript draft. Chapter 2 is published as Tay, W. S.; Li, Y.; Pullarkat, S. A.; Leung, P.-H. Divergent Reactivity of Phosphapalladacycles toward E–H (E = N, P, As) Bonds. Organometallics 2020, 39, 182. DOI: 10.1021/acs.organomet.9b00723. The contributions of the co-authors are as follows: • Dr Li, Y. collected and resolved the X-ray crystallographic data, • Dr Pullarkat, S. A. revised the manuscript draft and assisted in idea generation, • Prof Leung, P.-H. revised the manuscript draft and assisted in idea generation, • I designed the study, performed the experiments and analyzed the results, • I collected the Nuclear Magnetic Resonance (1H, 13C and 31P{1H}), High Resolution Mass Spectroscopy and melting point characterization data, and • I prepared the manuscript draft and Supporting Information. Chapter 2 is also published as Tay, W. S.; Yang, X.-Y.; Li, Y.; Pullarkat, S. A.; Leung, P.-H. Investigating Palladium Pincer Complexes in Catalytic Asymmetric Hydrophosphination and Hydroarsination. Dalton Trans. 2019, 48, 4602. DOI: 10.1039/C9DT00221A. Reproduced by permission of The Royal Society of Chemistry. The contributions of the co-authors are as follows: • Dr Yang, X.-Y. provided the pincer complexes used in the study, • Dr Li, Y. collected and resolved the X-ray crystallographic data, • Dr Pullarkat, S. A. revised the manuscript draft and assisted in idea generation, • Prof Leung, P.-H. revised the manuscript draft and assisted in idea generation, • I designed the study, performed the experiments and analyzed the results, • I collected the Nuclear Magnetic Resonance (1H, 13C and 31P{1H}), High Resolution Mass Spectroscopy, High Performance Liquid Chromatography, optical rotation and melting point characterization data, and • I prepared the manuscript draft and Supporting Information. Chapter 3 is published as Tay, W. S.; Yang, X.-Y.; Li, Y.; Pullarkat, S. A.; Leung, P.- H. Nickel Catalyzed Enantioselective Hydroarsination of Nitrostyrene. Chem. Commun. 2017, 53, 6307. DOI: 10.1039/C7CC02044A. Reproduced by permission of The Royal Society of Chemistry. The contributions of the co-authors are as follows: • Dr Yang, X.-Y. provided the pincer complexes used in the study, • Dr Li, Y. collected and resolved the X-ray crystallographic data, • Dr Pullarkat, S. A. revised the manuscript draft and assisted in idea generation, • Prof Leung, P.-H. revised the manuscript draft and assisted in idea generation, • I designed the study, performed the experiments and analyzed the results, • I collected the Nuclear Magnetic Resonance (1H, 13C and 31P{1H}), High Resolution Mass Spectroscopy, High Performance Liquid Chromatography, Elemental Analysis, optical rotation and melting point characterization data, and • I prepared the manuscript draft and Supporting Information. Chapter 3 is also published as Tay, W. S.; Lu, Y.; Yang, X.-Y.; Li, Y.; Pullarkat, S. A.; Leung, P.-H. Catalytic and Mechanistic Developments of the Nickel(II) Pincer Complex-Catalyzed Hydroarsination Reaction. Chem. Eur. J. 2019, 25, 11308. DOI: 10.1002/chem.201902138. The contributions of the co-authors are as follows: • Dr Lu, Y. contributed the computational calculations, • Dr Yang, X.-Y. provided the pincer complexes used in the study, • Dr Li, Y. collected and resolved the X-ray crystallographic data, • Dr Pullarkat, S. A. revised the manuscript draft and assisted in idea generation, • Prof Leung, P.-H. revised the manuscript draft and assisted in idea generation, • I designed the study, performed the experiments and analyzed the results, • I collected the Nuclear Magnetic Resonance (1H, 13C and 31P{1H}), High Resolution Mass Spectroscopy, High Performance Liquid Chromatography, optical rotation and melting point characterization data, and • I prepared the manuscript draft and Supporting Information. Chapter 4 is published as Tay, W. S.; Li, Y.; Yang, X.-Y.; Pullarkat, S. A.; Leung, P.- H. Air-stable phosphine organocatalysts for the hydroarsination reaction. J. Organomet. Chem. 2020, 914, 12126. DOI: 10.1016/j.jorganchem.2020.121216. The contributions of the co-authors are as follows: • Dr Li, Y. collected and resolved the X-ray crystallographic data, • Dr Yang, X.-Y. revised the manuscript draft and assisted in idea generation, • Dr Pullarkat, S. A. revised the manuscript draft and assisted in idea generation, • Prof Leung, P.-H. revised the manuscript draft and assisted in idea generation, • I designed the study, performed the experiments and analyzed the results, • I collected the Nuclear Magnetic Resonance (1H, 13C and 31P{1H}), High Resolution Mass Spectroscopy, High Performance Liquid Chromatography, Elemental Analysis and melting point characterization data, and • I prepared the manuscript draft and Supporting Information. Chapter 5 is published as Tay, W. S.; Li, Y.; Lu, Y.; Pullarkat, S. A.; Leung, P.-H. Chemoselective Synthesis and Evaluation of b-Oxovinylarsines as an Arsenic Synthetic Precursor. Organometallics 2020, 39, 271. DOI: 10.1021/acs.organomet.9b00587. The contributions of the co-authors are as follows: • Dr Li, Y. collected and resolved the X-ray crystallographic data, • Dr Lu, Y. contributed the computational calculations, • Dr Pullarkat, S. A. revised the manuscript draft and assisted in idea generation, • Prof Leung, P.-H. revised the manuscript draft and assisted in idea generation, • I designed the study, performed the experiments and analyzed the results, • I collected the Nuclear Magnetic Resonance (1H, 13C and 31P{1H}), High Resolution Mass Spectroscopy, High Performance Liquid Chromatography, Elemental Analysis, optical rotation and melting point characterization data, and • I prepared the manuscript draft and Supporting Information. 7 July 2020 . Date Tay Wee Shan Abstract The asymmetric hydroarsination reaction is arguably the most atom-economical and efficient manner to produce chiral arsines with high enantiopurities. Although various catalysts have been developed for the analogous hydrophosphination reaction, none have been effective for the hydroarsination reaction thus far. Herein, the development of organometallic (Pd- and Ni- based) and organic (phosphine-based) catalytic systems for the hydroarsination reaction is discussed. Mechanistic investigations reveal that arsines were not direct substitutes of phosphines in this instance. Consequently, arsines were applied in several novel applications such as in deuteration, decomplexation and as a directing group. The relevance of these developments to general synthetic chemistry is also outlined. 1 Acknowledgements “We cannot lie, we must be honest.”- My main supervisor, Prof Leung Pak-Hing, has been indispensable in this academic journey. I am especially grateful for the freedom he has given
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