University of Groningen Carbon-nitrogen bond formation via catalytic alcohol activation Yan, Tao

University of Groningen

Carbon-nitrogen bond formation via catalytic alcohol activation

Yan, Tao

IMPORTANT NOTE: You are advised to consult the publisher's version (publisher's PDF) if you wish to cite from

it. Please check the document version below.

Document Version

Publisher's PDF, also known as Version of record

Publication date:

2017

Link to publication in University of Groningen/UMCG research database

Citation for published version (APA):

Yan, T. (2017). Carbon-nitrogen bond formation via catalytic alcohol activation. University of Groningen.

Copyright

Other than for strictly personal use, it is not permitted to download or to forward/distribute the text or part of it without the consent of the author(s) and/or copyright holder(s), unless the work is under an open content license (like Creative Commons).

Take-down policy

If you believe that this document breaches copyright please contact us providing details, and we will remove access to the work immediately and investigate your claim.

Downloaded from the University of Groningen/UMCG research database (Pure): http://www.rug.nl/research/portal. For technical reasons the number of authors shown on this cover page is limited to 10 maximum.

Carbon-Nitrogen Bond Formation

via Catalytic Alcohol Activation

The work described in this thesis was carried out at the Stratingh Institute for

Chemistry, University of Groningen, The Netherlands.

This work was financially supported by University of Groningen.

Cover design by Tao Yan.

Printed by Ipskamp Printing, Enschede, The Netherlands.

ISBN: 978-94-034-0047-1 (printed version)

ISBN: 978-94-034-0046-4 (digital version)

faculty of science and

Carbon-Nitrogen Bond Formation

via Catalytic Alcohol Activation

PhD thesis

to obtain the degree of PhD at the

University of Groningen

on the authority of the

Rector Magnificus Prof. E. Sterken

and in accordance with

the decision by the College of Deans.

This thesis will be defended in public on

Monday 18 September 2017 at 12.45 hours

by

Tao Yan

born on 27 June 1990

in Anhui, China

Supervisors

Prof. B. L. Feringa

Prof. K. Barta

Assessment Committee

Prof. J. G. de Vries

Prof. B. de Bruin

Prof. M. Beller

Contents

Chapter 1

Borrowing hydrogen meets metal-ligand bifunctional

catalysis, an introduction to the thesis

1

Chapter 2

Iron catalyzed direct alkylation of amines with alcohols

21

Chapter 3

Benzylamines via iron catalyzed direct amination of

benzyl alcohols

49

Chapter 4

Pyrroles via Iron-Catalyzed N-Heterocyclization from

Unsaturated Diols and Primary Amines

75

Chapter 5

Direct N-alkylation of unprotected amino acids with

alcohols

93

Chapter 6

Ruthenium catalyzed N-alkylation of amino acid esters

with

121

Nederlandse samenvatting

141

English summary

143