Searching for new Mo(CO)6 reactions

Abstract

in situ

N

N

Populärvetenskaplig Sammanfattning påSvenska

List of Publications

I. Chemoselective Reduction of Tertiary Amides underThermal Control: Formation of either Aldehydes orAmines

Angewandte Chemie International Edition 2016 55

II. Transformation of Amides into Highly FunctionalizedTriazolines

ACS Catalysis 2017 7

III. Mild Reductive Functionalization of Amides intoN Sulfonylformamidines

ChemistryOpen 2017 6

IV. An Efficient One pot Procedure for the DirectPreparation of 4,5 Dihydroisoxazoles from Amides

Advanced Synthesis and Catalysis 2017 359

V. Facile Preparation of Pyrimidinediones andThioacrylamides by Reductive Functionalization ofAmides

Chemical Communications 2017 53

Papers not included as part of this thesis:

Chemoselective Reduction of Carboxamides

Chemical Society Reviews 2016 45

Third Generation Amino Acid Furanoside Based Ligands fromMannose for the Asymmetric Transfer Hydrogenation of

Ketones: Catalysts with an Exceptionally Wide Substrate Scope

Advanced Synthesis & Catalysis 2016 358

Bimetallic Catalysis: Asymmetric Transfer Hydrogenation ofSterically Hindered Ketones Catalyzed by Ruthenium andPotassium

ChemCatChem 2015 7

Mo(CO)6 Catalysed Chemoselective Hydrosilylation of, Unsaturated Amides for the Formation of Allylamines

Chemical Communications 2014 50

Ruthenium Catalyzed Tandem Isomerization/Asymmetric Transfer Hydrogenation of Allylic Alcohols

Chemistry A European Journal 2014 20

Automated Annotation and Quantification of Metabolites in1H NMR Data of Biological Origin

Analytical and Bioanalytical Chemistry 2012 403

Contents

N

Abbreviations

ee

p

1. Introduction

1.1 Amides

Figure 1. a) The resonance stabilization by the nitrogen lone pair, the origin ofthe stability. b) The orbital overlap that contributes to the planar conformationof the amides. c) Order of stability for different carbonyl compounds.

N

Scheme 1. Substitution reaction of non planar amide with methanol.

1.2 Reduction of Amides

Scheme 2. Different products formed in the reduction of amides through (a) C–Oand (b) C–N bond cleavage. c) Amide reduction into enamine.

1.2.1 Non Catalytic Reduction of Amides

in situ

N N

1.2.2 Catalytic Hydrogenation of Amides

et al.

Scheme 3. Chemoselective hydrogenation of a secondary amide containing anester moiety.

1.2.3 Catalytic Hydrosilylation of Amides

Figure 2. Structures of a few commercially available silanes used in hydrosilylations.

Scheme 4. Reaction mechanisms suggested for the hydrosilylation;a) Chalk Harrod, b) modified Chalk Harrod, c) bond metathesis and, d) Lewisacid catalyzed.

1.2.4 Chemoselective Reduction of Amides to Amines

et al.

R

R

Scheme 5. Chemoselective reduction as final step in the synthesis of(R) Verapamil.

A

B

Scheme 6. Chemoselective reduction by prior activation of the amide with Tf2O.

Scheme 7. Synthesis of Donepezil.

– epiConium maculatum

Scheme 8. Synthesis of (–) 2 epi pseudoconhydrine.

Scheme 9. Hydrosilylation protocols developed by the Nagashima group.

Scheme 10. Application of the hydrosilylation protocol developed by the Nagashima group in the synthesis of (+) Neostenine.

Scheme 11. Hydrosilylation protocols developed by the Beller group.

Scheme 12. Amide reduction developed by the Brookhart group.

Boc

Scheme 13. Hydrosilylation protocols developed by the Adolfsson group (a andb) and by Keinan and Perez (c).

Scheme 14. Synthesis of Naftifine by hydrosilylation.

Scheme 15. Hydrosilylation protocol developed by Blanchet.

1.2.5 Chemoselective Reduction of Amides to Aldehydes

hydrozirconation

Boc

in situ

in situ

Scheme 16. Hydrozirconation of amides into aldehydes developed by Georg.

B

Scheme 17. Chemoselective amide reduction developed by the Charette group.

i

Scheme 18. Hydrosilylation of tertiary amides followed by hydrolysis of theformed enamines resulted in aldehydes as final products.

1.3 Reductive Functionalization of Amides

in situ

Scheme 19. General scheme showing (a) electrophilic and (b and c) nucleophilicactivation and functionalization of amides.

1.3.1 Electrophilic Activation of Amides

A

CB

C B

Scheme 20. Different intermediates that can be formed by activation of amideswith triflic anhydride.

D E

F

a) b) c) d) e) f)

ReductionCitric acid

or aqueous NaHCO3

R4(SO)R5 1. R4mMXn

2. H3O+

Scheme 21. Transformations of amides using Tf2O/2 FPyr as activating reagent.

a

Scheme 22. Selected applications of the Tf2O activation of amides.

1.3.2 Nucleophilic Activation of Amides

N

Scheme 23. Chemoselective reductive nucleophilic addition developed by Chida.

N

TMS-CN

Scheme 24. Different nucleophiles used in the reductive functionalization ofamides by the Chida group.

N

Scheme 25. Activation and allylation of a N methoxy amide in the synthesis of(±) Gephyrotoxin.

N

Scheme 26. Alkylation of amides by prior formation of iminium ions.

Aspidospermaepi

Scheme 27. Alkylation of amides by the prior activation/reduction withIrCl(CO)(PPh3)2.

N

NN O

p

Scheme 28. Reductive functionalization developed by the Chida group, employing the IrCl(CO)(PPh3)2 based reduction protocol for the initial reduction.

1.4 Objectives of the Thesis

NN

2. Chemoselective Reduction of TertiaryAmides under Thermal Control (Paper I)

1a 3a

1a´

Scheme 29. a) Previous work. b) Temperature controlled hydrosilylation protocol.

1a’

N N N N

2a p 1b

2bN 2b

2d2e

2f 2gp

1h2h

2i 2j2k 2l

Boc 1j

2m 2q

1mN N

2r 2s

2b, 80% 2 h, 0 °C

3 h, r.t., 86%a

13 h, r.t., 83%b

2c, 67% 6 h, 65 °C

2d, 92% 3 h, r.t.

2e, 81% 48 h, –5 °C

2f,c 69% 5 h, 0 °C

2g,c 95% 24 h, –5 °C

2h,d 81% 5 h, 50 °C

2i, 88% 3 h, r.t.

2j, 62% 5 h, 40 °C

2k,e,f 79%9 h, 40 °C

2l, 74% 16 h, 50 °C

2m, 81% 10 h, 60 °C

2 h, r.t., 88%g

2n, 83% 3 h, 60 °C

2o, 86% 3 h, r.t.

2p,h 82% 5 h, 65 °C

2q, 88% 4 h, 50 °C

N

O

MeO2r,f 81% 24 h, r.t.

2s,f 80% 1 h, 40 °C

Scheme 30. Chemoselective formation of aldehydes from piperidine derived amides 1 (1.0 mmol), isolated yields. a Dibenzyl derived amide 1b’. b Morpholinederived amide 1b’’. c 1H NMR yields using 1,3,5 trimethoxybenzene as internalstandard. d Mo(CO)6 (10 mol%), TMDS (6.0 equiv). e TMDS (8.0 equiv). f Isolationwas performed on 0.5 mmol scale. g N,N dimethyl derived amide 1m’. h Mo(CO)6(10 mol%).

1b 1c

NN N 3b’ 3b’’ N N 3m’

3k 3u

1d 3d3f 3g 3t

1u3u

3h 3i 3v 3j 3m 3w 3m’3k

1r 1s3r 3s

3a, 97% 5 h, 80 °C

3b, 95% 2 h, 70 °C

3b’, 94% 3 h, 80 °C

3b’’, 77% 5 h, 80 °C

3c, 74% 24 h, 80 °C

3d, 92% 3 h, 80 °C

3t, 81% 3 h, 80 °C

3f: X = O, 82%a

3g: X = S, 78%b3u,c 68% 4 h, 80 °C

3h,d 74% 4 h, 80 °C

3i, 78% 3 h, 80 °C

3v, 79% 3 h, 80 °C

3j, 76% 4 h, 80 °C

3m: 4-CO2Me, 86%e

3w: 2-CO2Me, 81%f3m’, 70% 5 h, 80 °C

3k,g 68% 24 h, 80 °C

3r,g 79% 1 h, 80 °C

3s,g 88% 1 h, 80 °C

Scheme 31. Chemoselective formation of amines from amides (1.0 mmol), isolated yields. a 2 h, 65 °C. b 5 h, 65 °C. c 99% ee. d Mo(CO)6 (10 mol%), TMDS(2.0 mmol). e TMDS (2.0 equiv), 9 h, 80 °C. f 24 h, 65 °C. g Isolation was performedon 0.5 mmol scale.

3n 3p

Scheme 32. Chemoselective reduction of amides to amines.

1l p

6a vide infra

2.1 Competitive Study – Chemoselectivity

1b 3b4 2b

Scheme 33. Competitive reduction between amide 1b, ketone 4 and aldehyde 2b.

2.2 Applications of the Reduction Protocol

1d

2d

Scheme 34. Scale up reactions of the chemoselective and tunable amide reduction into aldehyde and amine.

5

5

Scheme 35. Employing the Mo(CO)6 catalyzed protocol for late stage functionalization in the synthesis of Donepezil.

2.3 Conclusions

2d 3d

3. Mo(CO)6 Catalyzed Enamine Formationfrom Amides (Papers II – V)

3.1 Introduction

Scheme 36. Enamine formation a) with acid catalysis, b) Pd catalyzed amination of vinyl halides, and c) hydroaminomethylation of alkenes.

viai

Scheme 37. Enamine synthesis by hydrosilylation a) employing stoichiometricamounts of Ti(OiPr)4, b) Ir catalysis, and c) base mediated amide hydrosilylation.

t

Scheme 38. Application of the hydrosilylation protocol in the synthesis of Turkiyenine.

viaA

B

R1N

OR3

R2H

M-H R1N

R3

R2H

H OMR1

NR3

R2H

R1N

R3

R2

HDeprotonation

Elimination

Iminium ionB

HemiaminalA

Enamine

Amide

Deprotonation

Reduction-OSiR3

Scheme 39. Suggested pathways for the formation of enamines by hydrosilylation.

3.2 Optimization

trans

Table 1. Optimization of reaction conditions for the enamine formation.a

Entry Solvent Time [h] Enamine 7a [%]b

6a

3.3 Scope

7b 7h

6b 6c 6f 6g 6h6g

6i 6j

vide infra 6k

7a, >95% 1 h

7b, >95% 3 h

7c, >95% 3 h

7d, >95% 1 h

7e, >95% 1 h

7f, >95%2 h, 75 °C

7g,a 85% 24 h

7h, 80% 2 h

7i, >95% 3 h

7j,a >95% 2 h

7k,b 67% 7 h

7l, 70% 2 h, 80 °C

7m, >95% 1 h

7n, 89% 5 h, 40 °C

7o, >95% 4 h

7p, >95% 0.5 h

7q, >95%3 h

7r, >95% 1 h

7s, >95% 2 h

7t, >95% 1 h

7u, >95% 5 h

7v, >95% 1 h

7w,c 88% 3 h

7x,a >95% 24 h

7y,d >95% 15 h

7z,a >95% 9 h

Scheme 40. Chemoselective formation of enamines from amides (0.5 mmol).1H NMR yields using 1,3,5 trimethoxybenzene as internal standard. a Mo(CO)6(5 mol%). b 1,4 dimethoxybenzene was used as internal standard. c Unpublishedresults. d Et3N (10 mol%) added.

6l

7l

7m 7n7o

6q6a

N 7s 7t7u 7v

7wN N 6x

N 6y

7z

6a 6p 6r

Table 2. Comparison between amides with different N substituents in the formation of enamines.a

Entry Amide Enamine [%]

6a 7a

6p 7p

6r 7r6

6aa 6ad6ae

6af

6ag6ah

6ai6aj

6ak

6al

6al

6aa 6ab 6ac 6ad

6ae 6af 6ag 6ah

6ai 6aj 6ak 6al

Scheme 41. Amides that did not successfully undergo enamine formation usingthe Mo(CO)6 catalyzed protocol.

trans 7k

3.4 Conclusions

e.g

4. Reductive Functionalization of Amides intoTriazolines and Triazoles (Paper II)

4.1 Introduction

Hi

Figure 3. Structures of triazoline and triazole.

Scheme 42. Cu catalyzed “Click” reaction between an alkyne and an azide forming triazole as product.

i

ACS Catalysis 2017 7triazolines triazoles.

e.g

in situet al.

p

Scheme 43. Synthesis of triazolines through a) 1,3 cycloaddition of azides withactivated olefins, b) cycloaddition with in situ formed enamines, c) triazole formation via triazoline intermediates.

in situ

4.2 Results

8a 7a9a

Scheme 44. One pot formation of triazolines from amides.

9d

7b7c

9d 6k9e

cis 6l9f

9g 9h 9i

9a, 91% 2 h

9b, 86% 2 h

9c, 88% 2 h

9d, 83% 2.5 h

9e,a,b 61% 15 h

9f, 66% 3 h

9g, 94% 2 h

9h, 84% 2.5 h

9i, 88% 3 h

Scheme 45. Evaluation of tertiary amides 6 in the chemoselective reduction andsubsequent cycloaddition reaction with enamines from amides (1 mmol) withorganic azide 8a, isolated yields. a Reaction performed at 60 °C. b Diastereomerswere obtained in a 2:1 ratio.

Scheme 46. Distribution of diastereomers for compound 9e.

6al

in situ

p8b

9j

Scheme 47. Tandem reaction for the aldehyde containing amide 6al (0.5 mmol)into the corresponding triazoline 9j.

Table 3. Comparison between enamines containing different N substituents inthe cyclization with phenyl azide (8).a

Entry Enamine Triazoline [%]

7a 9a

7p 9k

7r 9n6

7a 7p7r

7p

N 9k 9q

9k, 90% 3 h

9l, 72% 3 h

9m, 78% 1 h

9n, 92% 3 h

9o, 90% 5 h

9p,a 82% 5 h

9q,a 60% 3 h

Scheme 48. Evaluation of tertiary amides 6 in the chemoselective reduction andsubsequent cycloaddition reaction of enamines from amides (1 mmol), isolatedyields. a p CF3 phenyl azide (8b) was used.

9r9s 9t 9v 9aa 9y

9x 9ai 4aj 4ak9ah

9r, 92% 3 h

9s, 85% 3 h

9t, 93% 3 h

9u, 88% 2 h

9v, 78% 3 h, 65 °C

9w, 75% 15 h, 65 °C

9x, 88% 3 h, r.t.

9y, 79% 22 h, 50 °C

9z, 95% 3 h

9aa, 82% 3 h

9ab, 80%2 h

9ac, 85% 3 h

9ad, 92% 2 h

9ae, 89% 20 h

9af, 97% 3 h

9ag, 85% 7 h

9ah, 35% 3 h

9ai, 91% 3 h

9aj, 90% 3 h

9ak, 93% 3 h

Scheme 49. Evaluation of organic azides 8 in the chemoselective reduction andsubsequent cycloaddition reaction with enamines from amides 6 (1 mmol), isolated yields.

7g pp

8b 10a

10b

10c

10d 10e

10e

10a,a 58% 15 h, r.t.

10b,b,c 79% 24 h, 80 °C

10c,b 96% 65 h, 80 °C

10d,a,d 92% 3 h, 65 °C

10e,b,d 78% 2 h, r.t.

Scheme 50. Evaluation of tertiary amides 6 and azides 8 in the chemoselectivereduction and subsequent cycloaddition reaction with enamines from amides(1 mmol), isolated yields. a Piperidine derived amide was used. b Pyrrolidine derived amide was used. c Isolation was performed on 0.5 mmol scale. d KOH inmethanol (2M, 0.25 equiv) was added and reaction was left for additional 3 h at65 °C.

9aj10f

Scheme 51. Scale up reactions of the protocols for (a) triazoline and (b) triazoleformation.

4.3 Conclusions

5. Reductive Functionalization of Amides intoN Sulfonylformamidines (Paper III)

5.1 Introduction

et al.

et al

R1 NH2

O AlMe3 2.8 equivR2 NH2

R1 NH

OR2

R3

HN

R4

1. Ph3P / I2 1.5 equivEt3N 5.0 equiv

R1 N

NR2

R4

R1 NH2

NR2

R1 N

OR3

R2R4

HN

R5

1. Tf2O 1.3 equiv

R1 N

NR3

R5R4

R2 = H

R1 N

NR3

R4

R2 = alkylR5 = H

R2

or2.

2.

a)

b)

c) R3

R1 NR3 TsN3 1.5 equiv

CH2Cl2, r.t., 20 min

d)

R2 R1 N

NR3

R2

Ts

Scheme 52. Preparation of amidines through electrophilic amide activationa) by Charette and Grenon, b) Velavan et al. and c) Phakhodee et al.

N N

5.2 Results

11a9 N 12a

11a12a

6ae

Scheme 53. One pot formation of N sulfonylformamidine by reductive functionalization of amides.

N in situ 711a

N N 12b 12c12d 12e N N 12f N N

12g 12h 12i 12jN N 12k

12a, 78% 12b, 64% 12c,a 60%

12d, 68% 12e,a 57% 12f, 75%

SN

O O

NiPr

iPr

12g, 72% 12h, 66% 12i, 58%

12j, 39% 12k, 63%Scheme 54. Evaluation of tertiary amides 6 in the chemoselective reduction andsubsequent reaction of enamines from amides (1 mmol) with sulfonyl azide 11a,isolated yields. a p NO2 sulfonyl azide 11b was used.

N

12o 12t 12p 12x12w 12v

N 12z 12aa

12l, 50% 12m, 57% 12n, 50%

12o, 70% 12p, 49% 12q, 61%

12r, 63% 12s, 55% 12t, 60%

12u, 54% 12v, 79% 12w, 60%

12x, 47% 12y, 69%

12z, 83% 12aa, 58% Scheme 55. Evaluation of sulfonyl azides (11) in the chemoselective reductionand subsequent reaction of enamine from amide 6p (1 mmol) with sulfonyl azides, isolated yields.

N 12a

Scheme 56. Synthesis of N sulfonylformamidine 12a on a preparative scale.

9

10

N NH 10

N

12

Scheme 57. Proposed mechanism for the cleavage of the formed triazoline bya) Ramström, Yan and Houk, b) Li and co workers.

9

13

14via

13

Scheme 58. Proposed mechanism of triazoline decomposition leading toN sulfonylformamidine and aryldiazomethane (13) and trapping experimentwith benzoic acid to form ester 14.

5.3 Conclusions

N

N

N 12a

via 13

6. Reductive Functionalization of Amides into4,5 Dihydroisoxazoles (Paper IV)

6.1 Introduction

ii

in situ

Scheme 59. In situ preparation of nitrile oxides.

ii

Adv. Synth. Catal. 2017 3592 isoxazoline.

Scheme 60. Synthesis of 4,5 dihydroisoxazoles from (a) alkenes, (b) isolatedenamines and (c) in situ prepared enamines.

in situ,

N

ON

NO

N

SO2NH2ValdecoxibYield: 60%

N

Cl

OH

0.8 equiv

Et3N 1.1 equiv

DCM, 25 °C, 2 - 3 h

89% GC yield

69% GC yield

Scheme 61. Reported synthesis of Valdecoxib, a nonsteroidal anti infammatorydrug.

6.2 Results

in situ7p

16a15a

in situ 15a

16a

Table 4. Optimization of reaction conditions for the formation of 2 isoxazoline.a

Entry 15a [equiv] Additive [equiv] 2 Isoxazoline 16a [%]b

15a 6p7p

16a 16b16c 16d 16e

16f N N 16g 16h16i

N N 6w

16a, 84% 16b, 94% 16c, 84% 16d, 85%

16e, 93% 16f, 84% 16g,a 92% 16h, 79%

16i, 81% 16j, 93% 16k, 80% 16l, 91%

16m, 80% 16n, 55% 16o, 91%

16p, 93% 16q, 96% 16r,a 74%Scheme 62. Evaluation of tertiary amides 6 in the chemoselective reduction andsubsequent cycloaddition reaction with enamines from amides (1 mmol), isolatedyields. a Isolation was performed on 0.5 mmol scale.

16l 16j 16k16o

6c 6h

16m

16n6l

16o 16p 16q 16r6o

p 16s16t p 16u p 16v

16w

16x 16y

16s, 89% 16t, 91% 16u, 90% 16v, 87%

16w, 80% 16x, 89% 16y, 83%Scheme 63. Evaluation of hydroximinoyl chlorides 15 in the chemoselective reduction and subsequent cycloaddition reaction with enamine from amide 6p(1 mmol), isolated yields.

17

16a19

19

Scheme 64. a) Different regioisomers that can be formed in the 1,3 dipolar cycloaddition. b) Determination of the regioisomer formed under the developedreaction conditions.

6.3 Conclusions

via

7. Reductive Functionalization of Amides intoPyrimidinediones and Thioacrylamides(Paper V)

7.1 Introduction

et al.in situ

Scheme 65. (a) General structure of pyrimidinedione. Synthesis of pyrimidinediones by (b) cyclization and (c) dimerization of ynamides.

Scheme 66. The synthesis of thioacrylamides from enamines (a) and (b) amides.

7.2 Results

20a 7p21a 22a

22a

20a

6p22a

Scheme 67. Formation of pyrimidinedione 22a from enamine 7p.

7a 7p

N N 7r22a

Table 5. Comparison between enamines containing different N substituents inthe cyclization with phenyl isocyanate (20a).a

Entry Enamine Pyrimidinedione 22a [%]

7a

7p

7r6

22b 22c

6l 22d22e

22f 22g 22h22i

7f

20a p20b

22f

p 7g

22a,a 75% 22b, 92% 22c, 76%

22d, 57% 22e,a 85% 22f,a,b 85%

22g,a,c 64% 22h,d 71% 22i,d,e 76%

Scheme 68. Evaluation of amides 6 in the chemoselective reduction and subsequent functionalization with enamines from piperidine derivated amides(1 mmol), isolated yields. a Enamine from pyrrolidine derivated amide was used.b p Fluoro phenyl isocyanate 20b (3.5 equiv) was used, 65 °C, 72 h. c 65 °C, 16 h.d Isolation was performed on 0.5 mmol scale. e Phenyl isocyanate 20a (3.0 equiv)was used.

20N

22j

22k 22l 22m22n 22o

p

22j, 40% 22k,a 83% 22l,b 75%

N

N

OPh

O

CN

CN

22m, 94% 22n,a,c 86% 22o, 84%Scheme 69. Evaluation of aryl isocyanates 20 in the chemoselective reductionand subsequent functionalization with enamine from amide 6p (1 mmol), isolatedyields. a 65 °C, 16 h. b Isocyanate (3.0 equiv), 65 °C, 16 h. Isolation was performedon 0.5 mmol scale.

23a24a

25a

23a25a

6p25a6p

22

Scheme 70. Evaluation of phenyl isothiocyanate 23a in the synthesis of pyrimidinethione 24a. Formation of pyrimidinedione 22a from enamine 7p.

25a 25g

p 7g

25e N

25f 25g N N 25h

7p N N 7r 7a7q

25i25j 25k 25l

ptert

7p

25a, 94% 25b, 94% 25c, 75% 25d, 60%

25e, 89% 25f, 67% 25g, 39% 25h, 71%

25i, 83% 25j, 82%

25k, 94% 25l, 97%Scheme 71. Evaluation of amides (6) and isothiocyanates (23) in the chemoselective reduction and subsequent functionalization of enamines from amides(1 mmol), isolated yields.

257

25a26

d6

et al

N

Scheme 72. Hydrolysis of thioacrylamide 25a into the corresponding aldehyde26.

7.3 Conclusions

insitu

in situ

Concluding Remarks

N

N

Appendix A: Contribution List

I.

II.

III.

IV.

V.

Appendix B: Reprint Permissions

I.Angew. Chem. Int. Ed., 2016 55

II.

ACS Catalysis 2017 7

III.ChemistryOpen 2017 6

IV.Adv. Synth. Catal. 2017 359

V.Chem. Commun. 2017 53

Acknowledgements

Hans Adolfsson

Pher G. Andersson

Hasse Fredrik Paz Alexey ErikMarkus

Dr. Paz TrilloDr. Fredrik Tinnis Dr. Helena Lundberg Dr. Alexey Volkov Andrey Shatskiy Ida Pershagen Tove Kivijärvi Gabriella Kervefors

Fredrik Alexey Paz

Fredrik

Alexeythe hard way

Paz

Tove Gabriella

Berit Olofsson Nicklas Selander

Grasshopper

Broffice

Jenny Louise Sigrid Carin Kristina Ola MartinCarin

girl gangSara Johanna Tanja Elin Gabbi Tove

Department of Organic Chemistry

Knut & Alice Wallenbergs Stiftelse Ångpanneföreningens Forskningsstiftelse Gålöstiftelsen Stiftelsen Längmanska KulturfondenHelge Ax:on Johnsons stiftelse Vetenskapsrådet The Royal SwedishAcademy of Science

To all my friends and relatives, especially the Delzanno mob!

Moa Sara

Isabelle

mum dad

Frida

Erik

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