University of Groningen Sustainable pathways to bio-based amines via the 'hydrogen borrowing' strategy Afanasenko, Anastasiia

University of Groningen

Sustainable pathways to bio-based amines via the 'hydrogen borrowing' strategy Afanasenko, Anastasiia

DOI:

10.33612/diss.135979053

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Publication date: 2020

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Afanasenko, A. (2020). Sustainable pathways to bio-based amines via the 'hydrogen borrowing' strategy. University of Groningen. https://doi.org/10.33612/diss.135979053

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Appendix

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List of Abbreviations

BTX: benzene, toluene, and the three xylene isomers

CAPE: caffeic acid phenethylester

ChCl: choline chloride

CNS: central nervous system

CPME: cyclopentyl methyl ether

Cp*: pentamethylcyclopentadienyl

DCM: dichloromethane

DES: deep eutectic solvent

DMA: dimethylamine

DPEphos: bis[(2-diphenylphosphino)phenyl] ether

DPP: diphenyl phosphate

Dppf: 1,1'-bis(diphenylphosphino)ferrocene

EG: ethylene glycol

EDX: energy-dispersive X-ray spectroscopy

FAMEs: fatty acid methyl esters

FAOs: fatty alcohols

GC-FID: gas chromatography with flame ionization detector

GC-MS: gas chromatography mass spectrometry

HAADF-STEM: high-angle annular dark-field scanning transmission electron microscopy

5-HMF: 5-(hydroxymethyl)furfural

3-HP: 3-hydroxypropionic acid

HPLC: high-performance liquid chromatography

HRMS: high resolution mass spectrometry

HTC: hydrotalcite

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IC50: half maximal inhibitory concentration

LA: Lewis acid

LG: leaving group

MIC: minimum inhibitory concentration

Ms: mesyl, methanesulfonyl

NHC: N-heterocyclic carbene

NMR: nuclear magnetic resonance

NP: nanoparticle

OA: oxalic acid

PEG: polyethylene glycol

PG: protecting group

PIDA: phenyliodine(III) diacetate

PIFA: phenyliodine bis(trifluoroacetate)

TEM: transmission electron microscopy

THF: tetrahydrofuran

TLC: thin-layer chromatography

TMAO: trimethylamine N-oxide

TMDSO: tetramethyldisiloxane

TMS: tetramethylsilane

TPPMS: monosulfonated triphenylphosphane

(S)-TRIP: 3,3’-bis(2,4,6-triisopropylphenyl)-1,1’-binaphtyl-2,2’-diyl hydrogen phosphate

p-TSA or PTSA: p-Toluenesulfonic acid Ts: tosyl, p-toluenesulfonyl

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Appendix

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Short Biography

Education

Jul. 2018 – Aug. 2018 Research stay at University of Bath, Department of Chemistry, Bath, The United Kingdom

Collaborators: Prof. Dr. Ulrich Hintermair, Dr. Catherine Lyall, Dr. John P. Lowe

Research project: “N-alkylation of unprotected amino acids with alcohols applying DReaM (Dynamic Reaction

Monitoring) Facility”

Oct. 2016 – Oct. 2020 PhD candidate in Catalysis and Green Chemistry

University of Groningen, Faculty of Science and Engineering, Stratingh Institute for Chemistry, Groningen, The Netherlands

Promotor: Prof. Dr. Katalin Barta

Graduation work: “Sustainable pathways to bio-based amines via the 'hydrogen borrowing' strategy”

Apr. 2015 Research practice at Institute for Chemistry, Saint Petersburg State University Resource Center “X-ray diffraction methods of research”, Saint Petersburg, Russia

Sept. 2011 – Sept. 2016 MSc in Organic and Organometallic Chemistry (Diploma with highest academic distinction)

Saint Petersburg State University, Institute for Chemistry, Russia

Promotors: Dr. Tatyana G. Chulkova, Prof. Dr. Vadim Yu. Kukushkin

Graduation work: “New acyclic diaminocarbene complexes of platinum(II): synthesis, photophysical properties, and catalytic activity in the hydrosilylation reaction of unsaturated compounds”

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Appendix

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List of Publications

ORCID: https://orcid.org/0000-0001-7234-8290

During PhD studies:

1. Anastasiia Afanasenko†, Tao Yan†, Katalin Barta* († contributed equally)

Communications Chemistry, 2019, 2, 127−136

“Amination of hydroxyl acid esters via cooperative catalysis enables access to bio-based β-amino acid esters”

• Highlighted in the “Behind the paper” − “Taking the ‘high road’ to renewable beta-amino acids” https://go.nature.com/2QmZyxJ

2. Saravanakumar Elangovan, Anastasiia Afanasenko, Jörg Haupenthal, Zhuohua Sun, Yongzhuang Liu, Anna K. H. Hirsch, Katalin Barta*

ACS Cent. Sci., 2019, 5, 1707−1716

“From wood to tetrahydro-2-benzazepines in three waste-free steps: modular synthesis of biologically active lignin-derived scaffolds”

• Highlighted in the “cover picture” ACS Cent. Sci., 2019, 5, 10, 1625−1731 https://pubs.acs.org/toc/acscii/5/10

• C&EN News: Dalton, L: “Turning lignin into bioactive molecules in three green steps” https://cen.acs.org/synthesis/process-chemistry/Turning-lignin-bioactive-molecules-three/97/web/2019/10

3. Anastasiia Afanasenko, Rachael Hannah, Tao Yan, Saravanakumar Elangovan, Katalin Barta*

ChemSusChem, 2019, 12, 16, 3801−3807

“Ruthenium and Iron‐catalysed decarboxylative N‐alkylation of cyclic α‐amino acids with alcohols: sustainable routes to pyrrolidine and piperidine derivatives”

• Top downloaded paper 2018-2019: has been recognized as one of the most

read in ChemSusChem

4. Yongzhuang Liu, Anastasiia Afanasenko, Saravanakumar Elangovan, Zhuohua Sun, Katalin Barta*

ACS Sustain. Chem. Eng., 2019, 7, 13, 11267−11274

“Primary benzylamines by efficient N-alkylation of benzyl alcohols using commercial Ni catalysts and easy-to-handle ammonia sources”

5. Anastasiia Afanasenko, Saravanakumar Elangovan, Marc C. A. Stuart, Giuseppe Bonnura, Francesco Frusteri, Katalin Barta*

A-5 Cat. Sci. Technol. 2018, 8, 5498−5505

“Efficient N-alkylation of amines with alcohols using a simple-to-prepare nickel catalyst” 6. Zhuohua Sun, Giovanni Bottari†, Anastasiia Afanasenko†, Marc C. A. Stuart, Peter J. Deuss,

Bálint Fridrich, Katalin Barta* († contributed equally)

Nature Catalysis, 2018, 1, 82−92

“Complete lignocellulose conversion with integrated catalyst recycling yielding valuable aromatics and fuels”

The author also contributed to the following publications outside the scope of this thesis: 7. Anastasiia M. Afanasenko, Tatiana G. Chulkova*, Irina A. Boyarskaya, Regina M. Islamova,

Anton A. Legin, Bernhard K. Keppler, Stanislav I. Selivanov, Anatoly N. Vereshchagin, Michail N. Elinson, Matti Haukka

Journal of Organometallic Chemistry, 2020, 923, 121435−121443

“C,N-chelated diaminocarbene platinum(II) complexes derived from 3,4-diaryl-1H-pyrrol-2,5-diimines and cis-dichlorobis(isonitrile) platinum(II): Synthesis, cytotoxicity, and catalytic activity in hydrosilylation reactions”

8. Anastasiia M. Afanasenko, Alexander S. Novikov, Tatiana G. Chulkova*, Yakov M. Grigoriev, Ilya E. Kolesnikov, Stanislav I. Selivanov, Galina L. Starova, Andrey A. Zolotarev, Anatoly N. Vereshchagin, Michail N. Elinson

Journal of Molecular Structure, 2020, 1199, 126789−126797

“Intermolecular interactions-photophysical properties relationships in phenanthrene-9,10-dicarbonitrile assemblies”

9. Anastasiia M. Afanasenko, Alexander S. Novikov, Tatiana G. Chulkova*, Yakov M. Grigoriev, Ilya E. Kolesnikov, Stanislav I. Selivanov, Galina L. Starova, Andrey A. Zolotarev, Anatoly N. Vereshchagin, Michail N. Elinson

Data in Brief, 2019, 27, 104605−104622

“Structural data of phenanthrene-9,10-dicarbonitriles”

10. Anastasiia M. Afanasenko, Dina V. Boyarskaya, Irina A. Boyarskaya, Tatiana G. Chulkova*, Yakov M. Grigoriev, Ilya E. Kolesnikov, Margarita S. Avdontceva, Taras L. Panikorovskii, Andrej I. Panin, Anatoly N. Vereshchagin, Michail N. Elinson

Journal of Molecular Structure, 2017, 1146, 554−561

“Structures and photophysical properties of 3,4-diaryl-1H-pyrrol-2,5-diimines and 2,3-diarylmaleimides”

11. Anastasiia M. Afanasenko, Margarita S. Avdontceva, Alexander S. Novikov, Tatiana G. Chulkova*

Zeitschrift fuer Kristallographie - Crystalline Materials, 2016, 231, 7, 435−440

“Halogen and hydrogen bonding in cis-dichlorobis(propionitrile)platinum(II) chloroform monosolvate”

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12. Anastasiia M. Afanasenko, Evgeny Yu. Bulatov, Tatiana G. Chulkova*, Matti Haukka, Fedor M. Dolgushin

Transition Metal Chemistry, 2016, 41, 4, 387−392

“An efficient method for selective oxidation of (oxime)Pt(II) to (oxime)Pt(IV) species using N,N-dichlorotosylamide”

13. Evgeny. Yu. Bulatov, Anastasiia M. Afanasenko, Tatiana G. Chulkova*, Matti Haukka ActaCryst., 2014, E70, m7−m8

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Appendix

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Acknowledgments

This thesis is the result of collective endeavours, and I would like to express my gratefulness to all people who have contributed to it.

First and foremost, I would like to thank my supervisor, Prof. Dr. Katalin Barta for giving me an opportunity to conduct my PhD research in her group. Dear Katalin, I am extremely grateful to you for everything: we did great science and overcome many hurdles, and it would be impossible without your wise guidance, patience, and endless enthusiasm. I deeply appreciate the confidence you have put into me, as well as freedom you have given to me. Thank you for believing in me. You have been even more than an advisor and formal boss for me, you have been my mentor in science!

I would like to thank members of the Assessment Committee (Prof. Dr. J. G. Roelfes, Prof. Dr. J. S. M. Samec, Prof. Dr. N. Yan) for useful comments and suggestions.

Without the contribution of our collaborators some of the projects would not be possible. I would like to acknowledge Prof. Dr. Anna K. H. Hirsch and Dr. Jörg Haupenthal for the evaluation of biological activity of our compounds (collaboration detailed in Chapter 5), Dr. Giuseppe Bonura and Dr. Francesco Frusteri for the TEM measurements (collaboration detailed in Chapter 2). I am very much appreciative of Prof. Dr. Ulrich Hintermair and his group at the University of Bath, the United Kingdom, as well as DReaM scientific advisory board, especially Dr. Catherine Lyall and Dr. John P. Lowe. Thank you for hosting me for two weeks and teaching me FlowNMR spectroscopy.

I would like to thank all groups of the Stratingh Institute, especially the Otto, Harutyunyan, Roelfes, Browne, Otten, Klein, Mayer, Minnaard and Feringa groups. I am thankful to all staff of the Stratingh Institute for Chemistry for the nice working environment and fruitful discussions during the institute meetings. I would like to separately thank Prof. Dr. Edwin Otten for the help with XRC and Prof. Dr. Marc C. A. Stuart for the TEM measurements. Also, I am extremely obliged to Gaël for help and advice. I am very grateful to Pieter and Johan for the help with NMR, Theodora and Renze for HRMS measurement, Monique for GC-MS, GC-FID, HPLC support, Oetze for the help with gloveboxes. I am deeply indebted to Annette and Tineke for the secretarial support.

I also would like to thank our collaborators and good friends from the Department of Chemical Engineering: Dr. Peter J. Deuss – it was a great pleasure to work with you and create exam questions, I think we worked as a great cohesive team and Dr. Patrizio Raffa – thank you so much for “music evenings” with our the best-ever band “No clue” and for your help, support and advice, all the best to your scientific career.

To my dear paranymphs: Dear Bálint, my dear brother, I have a feeling that I have known you all my life. Without your heart warmth, support, advice, and understanding (sometimes it is not necessary to tell even anything, probably it is telepathy), I would not be able to overcome all

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the troubles. Thank you for our “Flights” and “Evenings of Titanic”. Dear Ale, a very strong and independent Italian woman, I admire your perseverance and selflessness in everything that you are doing. Thank you for supporting me to join the rowing club, it was an amazing experience, we were a great team! I will never forget how we tried to learn Dutch rowing terms and our final exam.

Dear former and present members of the Barta group – my dear “BartaCats” and “Monolignols”: I have been lucky that I have met and had a chance to work with all of you. Dear Giovanni, we have worked together in the one fume hood just for 3 months, but I will never forget your singing and the sunshine that you brought to the lab. It was a great pleasure to meet with you in London in July 2018. Dear Tao, thank you a lot for mentoring and advice, you have inspired me and fostered my self-development as a person and as a chemist. Dear Zhuohua, it was a great pleasure to work with you, all the best to your future independent scientific career. Dear Saravana, my dear Boss, and a real friend, I deeply indebted to you for your advice, discussions, and guidance. I have learned a lot from you! Thank you for evening lab discussions and coffee breaks. Dear Noemi, thank you a lot for the countless chocolate and a nice atmosphere in the group. Dear Mattia, the greatest speedskater, it was a great surprise to meet with you on the skating rink! Thank you for the sports and social life updates. Dear Antonio, thank you for your creativity and musical inspirations. Dear Maxim, thank you for the countless work discussions, research ideas, and questions. You are an excellent chemist and I wholeheartedly convinced that you will achieve great success as a group leader. 亲爱的刘老 师（现在已经是刘老板）、我的第一位、是最好的中文老师、 我要对您表示我的非常 感谢！感谢您的知识、您的耐心、支持和建议！您是一个美妙的化学家、同事和朋友 ！我非常想您！亲爱的先元，我可爱的同事！你是一个非常努力和有上进心的人、 保 持良好的工作! 我相信你会取得巨大成功! 我会想你！Henrique, Henk-Jan, Gwen, Lars, Hugo, Marlene, Douwe, Ada, Thomas, Bálint, Pascal, Daniel, I am very happy to meet with all of you and thank you for keeping the amazing working environment in Barta group.

To my dear students: Dear Marilena, my first student, you are a very motivated and inquisitive researcher, it was a great pleasure to work with you! Dear Rachael, thank you a lot for your hard, selfless work! I am very happy that you have decided to pursue PhD studies, I am not doubting that you will succeed! Dear Aman, you did a great job, please keep your passion for science, I do believe you will have a big scientific future!

I would like to thank my dear friends and teachers outside the Stratingh Institute: Groningen Confucius Institute (亲爱的老师：王洋，江薇，魏玉竹), speedskating clubs “SPR-KRAS” and “GSSV Tjas”, running clubs (especially Rink Hooijsma), and “K.G.R. De Hunze” (especially Erik Ader). I am extremely happy and proud to be part of all of them and deeply grateful for knowledge and inspiration.

To my family: Дорогие родители, я очень Вам благодарна за Вашу безграничную любовь и заботу. Благодаря Вашим мудрым советам, сопереживанию и поддержке, я смогла преодолеть все трудности на этом важном для меня этапе жизни и выросла как в

A-9 профессиональном, так и в личностном плане. Спасибо Вам за всё, своим успехом я обязана Вам!

I remain indebted and grateful,

Anastasiia (Nastya, 艾娜)

Groningen, September 28th, 2020