Boron catalysis in Organic Chemistry

137 Pages·2017·2.21 MB·English

Delft University of Technology

Boron catalysis in Organic Chemistry
Mueller, Tobias
DOI
10.4233/uuid:be20a738-9cd9-424f-ae39-611f0dca8010
Publication date
2016
Document Version
Final published version
Citation (APA)
Mueller, T. (2016). Boron catalysis in Organic Chemistry. https://doi.org/10.4233/uuid:be20a738-9cd9-424f-
ae39-611f0dca8010
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Boron catalysis in Organic Chemistry

Tobias Müller
Cover design by Tobias Müller and Bogdan Kalušević.
Boron catalysis in Organic Chemistry

Proefschrift

ter verkrijging van de graad van doctor
aan de Technische Universiteit Delft,
op gezag van de Rector Magnificus prof. ir. K. C. A. M. Luyben,
voorzitter van het College voor Promoties,
in het openbaar te verdedigen op

vrijdag 17 juni 2016 om 10.00 uur

door

Tobias MÜLLER
Diplom Chemiker,
Universität Ulm, Duitsland,
geboren te Ulm, Duitsland
Dit proefschrift is goedgekeurd door de
promotoren: Prof. dr. I. W. C. E Arends en Prof. dr. U. Hanefeld

Samenstelling promotiecommissie:
Rector Magnificus voorzitter
Prof. dr. I. W. C. E. Arends Technische Universiteit Delft, promotor
Prof. dr. U. Hanefeld Technische Universiteit Delft, promotor

Onafhankelijke leden:
Prof. dr. E. J. R. Sudhölter Technische Universiteit Delft
Prof. dr. G. A. van der Marel Universiteit Leiden
Prof. dr. J. Schatz Friedrich Alexander Universität Erlangen
dr. J. van Haveren Universiteit Wageningen
Prof. dr. ir H. van Bekkum Technische Universiteit Delft, reservelid

Ander lid:
dr. K. Djanashvili Technische Universiteit Delft

This research has been performed within the framework of the CatchBio program. The support of the Smart Mix
Program of the Netherlands Ministry of Economic Affairs and the Netherlands Ministry of Education, Culture and
Science is gratefully acknowledged.

ISBN: 978-94-6186-666-0

Copyright (cid:211) 2016 by Tobias Müller

All rights reserved. No part of the material protected by this copyright notice may be reproduced or utilized in any
form or by any other means, electronic or mechanical, including photocopying, recording or by any information
storage and retrieval system, without written permission from the author.

Printed in the Netherlands
“We cannot change the cards we are dealt, just how we play the hand”
Randy Pausch, The Last Lecture (18 September 2007)

To my German and Serbian family

Für meine Deutsche und Serbische Familie

Mojoj nemačkoj i srpskoj porodici
VI
CONTENTS

Chapter 1 Introduction 1

Chapter 2 Synthesis of tetrahedral boron salts as potential 21
catalysts

Chapter 3 Boron catalyzed reactions 41

Chapter 4 Aldol reactions mediated by a tetrahedral boronate 65

Chapter 5 Tetrahedral boronates as basic catalysts 87
in the aldol reaction

Chapter 6 Summary 113
Contents

List of publications 121

Acknowledgements 123

Curriculum Vitae 127
VIII
Introduction

1