Highly active C-H acids for catalysis: design and application
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|---|---|
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| Language: | English |
| Published: |
Köln
2018
|
| Subjects: | |
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|---|---|---|---|
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| 003 | DE-604 | ||
| 005 | 20190724 | ||
| 007 | t | ||
| 008 | 190124s2018 gw a||| m||| 00||| eng d | ||
| 015 | |a 18,H12 |2 dnb | ||
| 016 | 7 | |a 1169447422 |2 DE-101 | |
| 020 | |c Broschur | ||
| 035 | |a (OCoLC)1090100477 | ||
| 035 | |a (DE-599)DNB1169447422 | ||
| 040 | |a DE-604 |b ger |e rda | ||
| 041 | 0 | |a eng | |
| 044 | |a gw |c XA-DE | ||
| 049 | |a DE-355 |a DE-29T |a DE-83 | ||
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| 100 | 1 | |a Höfler, Denis |d 1989- |e Verfasser |0 (DE-588)1165183900 |4 aut | |
| 245 | 1 | 0 | |a Highly active C-H acids for catalysis |b design and application |c vorgelegt von Denis Höfler aus Tettnang |
| 264 | 1 | |a Köln |c 2018 | |
| 300 | |a IX, 286 Seiten |b Illustrationen |c 21 cm | ||
| 336 | |b txt |2 rdacontent | ||
| 337 | |b n |2 rdamedia | ||
| 338 | |b nc |2 rdacarrier | ||
| 502 | |b Dissertation |c Universität zu Köln |d 2018 | ||
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| adam_text | TABLE O F CONTENTS
KURZZUSAMMENFASSUNG/ABSTRACT...................................................................................................V
LIST OF
ABBREVIATIONS............................................................................................................................VI
1
INTRODUCTION...............................................................................................................................................
1
2
BACKGROUND.................................................................................................................................................
3
2.1 C-H A
CIDS
.................................................................................................................................................
5
2.2 C
HIRAL
S
ULFOXIDES
..................................................................................................................................8
3
OBJECTIVES....................................................................................................................................................10
3.1 C
HIRAL
P
HOSPHONYL
C-H A
CIDS
FOR
A
SYMMETRIC
C
ATALYSIS
.....................................................
10
3.2 A
LLYLIC
C-H A
CIDS
................................................................................................................................
11
3.2.1 IMPROVED ACCESS TO ALLYLIC BINAPHTHYL-BASED C-H (BALT) A CIDS
...................................
11
3.2.2 DEVELOPMENT OF HIGHLY REACTIVE ALLYLIC C-H A
CIDS............................................................. 11
3.3 T
RIENE
-B
ASED
C-H A
CIDS
.....................................................................................................................12
3.4 C
HIRAL
, E
NANTIOPURE
S
ULFOXIDE
C-H
ACIDS
...................................................................................
13
4 RESULTS AND
DISCUSSION.......................................................................................................................
14
4.1 C
HIRAL
P
HOSPHONYL
C-H A
CIDS
..........................................................................................................14
4.2 A
LLYLIC
C-H A
CIDS
................................................................................................................................
16
4.2.1 BINAPHTHYL-ALLYL-TETRASULFONE (BALT) C-H A CIDS
...............................................................
16
4.2.2 SYNTHESIS OF 1,1,3,3-TETRATRIFLYLPROPENE
(TTP).......................................................................20
4.2.3 APPLICATION OF
TTP......................................................................................................................24
4.2.4 1,1,3,3-TETRANONAFLYLPROPENE
(TNP).........................................................................................30
4.3 T
RIENE
-B
ASED
C-H
ACIDS
......................................................................................................................32
4.3.1 DESIGN OF HEXATRIFLYLTRIMER
(HTT)...........................................................................................32
4.3.2 A PURELY ORGANIC
TRICARBANION.................................................................................................
33
4.3.3 VINYLOGOUS
TTP..........................................................................................................................
39
4.3.4 SYNTHESIS OF HEXATRIFLYLTRIMER (HTT)
.......................................................................................
42
4.3.5 HEXAPHENYLSULFONYLTRIMER
(HPT)..............................................................................................
44
4.3.6 CHIRAL BINAPHTHYL-BASED TRIMER
(CBT)...................................................................................
45
4.3.7 TOWARDS VINYLOGOUS BALT C-H
ACIDS....................................................................................
47
4.4 C
HIRAL
, E
NANTIOPURE
S
ULFOXIDE
C-H
ACIDS
...................................................................................
50
4.4.1 SULFINYL C-H
ACIDS......................................................................................................................50
4.4.2 APPLICATION OF SULFINYL C-H ACIDS TO ASYMMETRIC CATALYSIS
................................................
52
4.4.3 TOWARDS BIS(SULFINYL) C-H A
CIDS.............................................................................................
56
4.5 A
CIDITY
OF
C-H
ACIDS
...........................................................................................................................
58
5
SUMMARY........................................................................................................................................................
60
5.1 C
HIRAL
P
HOSPHONYL
C-H A
CIDS
.........................................................................................................
61
5.2 A
LLYIC
C-H A
C ID S
.................................................................................................................................62
5.2.1 IMPROVED SYNTHESIS OF BALT C-H
ACIDS...........................................................................
62
5.2.2 TETRATRIFLYLPROPENE
(TTP).....................................................................................................64
5.2.3 TETRANONAFLYLPROPENE
(TNP)................................................................................................
65
5.3
T
R IE N E
-B
A S E D
C-H
A
C I D S
..............................................................................................................
66
5.3.1 A PURELY ORGANIC
TRICARBANION............................................................................................
66
5.3.2 VINYLOGONS
TTP...................................................................................................................
67
5.3.3 HEXATRIFLYLTRIMER
(NTT).......................................................................................................68
5.3.4 HEXAPHENYLSULFONYLTRIMER (HPT), CHIRAL BINAPHTHYL-BASED TRIMER
(CBT), AND TOWARDS
VINYLOGOUS BALT C-H
ACIDS.............................................................................................
69
5.4 C
HIRAL
S
ULFOXIDE
C-H A
CIDS
.............................................................................................................70
5.4.1 SULFINYL C-H
ACIDS..............................................................................................................
70
5.4.2 TOWARDS BIS(SULFINYL) C-H
ACIDS........................................................................................71
6
OUTLOOK.....................................................................................................................................................
72
6.1 P
HOSPHONYL
C-H
A
CIDS
........................................................................................................................72
6.2
A
L L Y L IC
C-H
A
C I D S
.........................................................................................................................73
6.2.1 BINAPHTHYL-ALLYL-TETRASULFONE (BALT) C-H ACIDS
...........................................................
73
6.2.2 TETRATRIFLYLPROPENE
(TTP).....................................................................................................73
6.2.3 TETRANONAFLYLPROPENE (TNP)
................................................................................................
74
6.3
T
R IE N E
-B
A S E D
C-H
A C ID S
...............................................................................................................
75
6.3.1 A PURELY ORGANIC
TRICARBANION............................................................................................
75
6.3.2 VINYLOGOUS TTP
(VTTP).......................................................................................................75
6.3.3 HEXATRIFLYLTRIMER
(HTT).......................................................................................................76
6.3.4 HEXAPHENYLSULFONYLTRIMER (HPT), CHIRAL BINAPHTHYL-BASED TRIMER
(CBT), AND VINYLOGOUS
BALT C-H A
CIDS.......................................................................................................................76
6.4 C
HIRAL
S
ULFOXIDE
C-H A
C ID S
.........................................................................................................77
7 EXPERIMENTAL
PART............................................................................................................................78
7.1
G
E N E R A L
E
X P E R IM E N T A L
C
O N D I T I O N S
................................................................................................
78
7.2 P
HOSPHONYL
C-H A
CIDS
........................................................................................................................83
7.3
A
L L Y L IC
C-H
A
C ID S
................................................................................................................................85
7.3.1 SYNTHESIS OF BINAPHTHYL-ALLYL-TETRASULFONES
(BALTS).........................................................85
(S)-[ 1,1 *-BINAPHTHALENE]-2,2 -DITHIOL
(67)................................................................................................................
85
(5 DINAPHTHO[2,1 -D: 1 ,2 -F|[L,3]DITHIEPINE
(66)....................................................................................................
85
(S)-4H-DINAPHTHO[2,1 -D: 1 2 -F][ 1,3]DITHIEPINE 3,3,5,5-TETRAOXIDE
(53)................................................................ 86
(S)-2,6-BIS(TRIMETHYLSILYL)-4H-DINAPHTHO[2,L-D: 1 2 -F][1,3]DITHIEPINE
3,3,5,5-TETRAOXIDE (65)............................87
(S)-2,6-DIIODO-4H-DINAPHTHO[2,1 -D: 1 ,2 -F][ 1,3]DITHIEPINE
3,3,5,5-TETRAOXIDE (54)..............................................87
(5 2,6-DI(PHENANTHREN-9-YL)-4H-DINAPHTHO[2,1 -D: 1 2 *-F][
1,3]DITHIEPINE 3,3,5,5-TETRAOXIDE (64)
........................
88
(S)-4-(2,2-BIS((TRIFLUOROMETHYL)SULFONYI)VINYL)-2,6-DI(PHENANTHREN-9-YL)-4H-DINAPHTHO[2,L-D:L ,2 -
F][L,3]DITHIEPINE 3,3,5,5-TETRAOXIDE
(63A)...............................................................................................................109
7.3.2 SYNTHESIS OF TETRATRIFLYLPROPENE (TTP)
..................................................................................
113
2-ETHOXY-L, 1 -BIS((TRIFLUOROMETHYL)SULFONYL)ETHANE
(69):......................................................................................
113
2,2,6,6-TETRAMETHYLPIPERIDIN-L-IUM
1,1,3,3-TETRAKIS((TRIFLUOROMETHYL)SULFONYL)PROP-2-EN-L -IDE (TTP*TMP,
75):
...............................................................................................................................................................................
113
ILL
1.1.3.3- TETRA((TRIFLUOROMETHYL)SULFONYL)PROP-L-ENE
(TTP)...............................................................................118
TETRAETHYLAMMONIUM
1,1,3,3-TETRAKIS((TRIFLUOROMETHYL)SULFONYL)PROP-2-EN-1 -IDE (ET4N+TTP~,
78)
...................
124
SILVER(I) L,L,3,3-TETRAKIS((TRIFLUOROMETHYL)SULFONYL)PROP-2-EN-L-IDE
(AG+TTP~, 77)
............................................
129
LITHIUM L,L,3,3-TETRAKIS((TRIFLUOROMETHYL)SULFONYL)PROP-L-ENE (LFTTP-,
76)...................................................... 130
7.3.3 SYNTHESIS OF TETRANONAFLYLPROPENE (TNP)
...........................................................................
131
BIS(NONAFLUOROBUTYLSULFONYL)METHANE
(90):..........................................................................................................
131
2-ETHOXY-1,1 -BIS((NONAFLUOROBUTYL)SULFONYL)ETHANE
(91):.....................................................................................
131
2.2.6.6- TETRAMETHYLPIPERIDIN-L-IUM
L,L,3,3-TETRAKIS((NONAFLUOROBUTYL)SULFONYL)PROP-2-EN-L-IDE (TNP-TMP, 94)
140
1.1.3.3- TETRA((NONAFLUOROBUTYL)SULFONYI)PROP-L-ENE
(TNP).............................................................................156
7.4 S
YNTHESIS
OF
T
RIENE
-B
ASED
C-H
ACIDS
..........................................................................................
157
7.4.1 TRICARBANION SALT 9 8
...................................................................................................................159
7.4.2 VINYLOGOUS TTP
(VTTP)...........................................................................................................
181
TETRAETHYLAMMONIUM
()-L,L,5,5-TETRAKIS((TRIFLUOROMETHYL)SULFONYL)PENTA-2,4-DIEN-L-IDE
(ET4N SALT OF
VINYLOGOUS TTP,
101).............................................................................................................................................181
7.4.3 SYNTHESIS OF HEXATRIFLYLTRIMER
(HTT)......................................................................................188
2.2.6.6- TETRAMETHYLPIPERIDIN-L-IUM
3-(2,2-BIS((TRIFLUOROMETHYL)SULFONYL)VINYL)-L,1,5,5-
TETRAKIS((TRIFLUOROMETHYL)SULFONYL)PENTA-1,4-DIEN-3-IDE (TMP-HTT, 107)
...........................................................
188
HEXATRIFLYLTRIMER (HTT,
3-(2,2-BIS((TRIFLUOROMETHYL)SULFONYL)VINYL)-L,L,5,5-
TETRAKIS((TRIFLUOROMETHYL)SULFONYL)PENTA-1,3-DIENE)..............................................................................................
201
HEXATRIFLYLTRIMER ETHERATE
(108)............................................................................................................................
205
7.4.4 HEXAPHENYLSULFONYLTRIMER
(HPT)............................................................................................
214
(3-(2,2-BIS(PHENYLSULFONYL)ETHYLIDENE)PENTA-1,4-DIENE-1,1,5,5-TETRAYL-1,1,5,5-TETRASULFONYL)TETRABENZENE
(HPT)
................................................................................................................................................................................
214
7.4.5 CHIRAL BINAPHTHYL-BASED TRIMER
(CBT).................................................................................
216
(4,4 )-4,4 -(2-((3,3,5,5-TETRAOXIDO-4H-DINAPHTHO[2,1 -D: 1 2 -F)[
1,3]DITHIEPIN-4-YL)METHYLENE)PROPANE-L,3-
DIYLIDENE)BIS(4H-DINAPHTHO[2,1 -D: 1 ,2 -F][L,3]DITHIEPINE
3,3,5,5-TETRAOXIDE) (CBT)...........................................216
7.4.6 TOWARDS VINYLOGOUS BALT C-H
ACIDS.................................................................................
217
(S)-2,2 -DIMETHOXY-1,1 -BINAPHTHALENE
(113)........................................................................................................
217
(5 (2,2 -DIMETHOXY-[ 1,1 -BINAPHTHALENE]-3,3*-DIYL)DIBORONIC ACID
(50).............................................................. 217
(5R)-3,3 -BIS(3,5-BIS(TRIFLUOROMETHYL)PHENYL)-2,2 -DIMETHOXY-L,L,-BINAPHTHALENE
(114)
......................................
218
(5)-3,3 -BIS(3,5-BIS(TRIFLUOROMETHYL)PHENYL)-[L,L -BINAPHTHALENE]-2,2 -DIOL
(115)..............................................218
(5)-0,0 -(3,3 -BIS(3,5-BIS(TRIFLUOROMETHYL)PHENYL)-[L,L -BINAPHTHALENE]-2,2 -DIYL)
BIS(DIMETHYLCARBAMOTHIOATE)
(116)
...................................................................................................................................................................
219
(5)-S,S -(3,3 -BIS(3,5-BIS(TRIFLUOROMETHYL)PHENYL)-[L,L,-BINAPHTHALENE]-2,2,-DIYL)
BIS(DIMETHYLCARBAMOTHIOATE)
(117)
...................................................................................................................................................................
220
(S)-3,3 -BIS(3,5-BIS(TRIFLUOROMETHYL)PHENYL)-[L,L -BINAPHTHALENE]-2,2*-DITHIOL
(118)..........................................220
(5)-2,6-BIS(3,5-BIS(TRIFLUOROMETHYL)PHENYL)DINAPHTHO[2,L-D:L*,2 -F][L,3]DITHIEPINE(LI9)
..................................
221
(5)-2,6-BIS(3,5-BIS(TRIFLUOROMETHYL)PHENYL)-4H-DINAPHTHO[2,1 -D: 1
,2 -F][ 1,3]DITHIEPINE 3,3,5,5-TETRAOXIDE (59)
...............................................................................................................................................................................
222
(5,)-4-(2-((J5)-((5,)-2,6-BIS(3,5-BIS(TRIFLUOROMETHYL)PHENYL)-3,3,5,5-TETRAOXIDO-4H-DINAPHTHO[2,L-D:R,2 -
F][L,3]DITHIEPIN-4-YLIDENE)METHYL)-3-(DIMETHYLAMINO)ALLYLIDENE)-2,6-BIS(3,5-BIS(TRIFLUOROMETHYL)PHENYL)-4H-
DINAPHTHO[2,1 -D: 1 ,2*-F][L,3]DITHIEPINE 3,3,5,5-TETRAOXIDE
(112)...........................................................................222
7.5 S
YNTHESIS
OF
C
HIRAL
, E
NANTIOPURE
S
ULFOXIDES
..........................................................................
224
7.5.1 SULFINYL C-H
ACIDS.................................................................................................................
224
SODIUM 1,1,2,2,3,3,4,4,4-NONAFLUOROBUTANE-L -SULFINATE
(122)..............................................................................
224
1.1.2.2.3.3.4.4.4- NONAFLUOROBUTANE-L-SULFINIC ACID
(123)................................................................................224
1.1.2.2.3.3.4.4.4- NONAFLUOROBUTANE-L-SULFINIC CHLORIDE
(120).........................................................................
225
(4#)-3-((PERFLUOROBUTYL)SULFINYL)-4-PHENYLOXAZOLIDIN-2-ONE (124)
.....................................................................
225
RACEMIC
L-((BIS((TRIFLUOROMETHYL)SULFONYL)METHYL)SULFINYL)-L,L,2,2,3,3,4,4,4-NONAFLUOROBUTANE
(56)...............230
ENANTIOPURE
(/?)-L-((BIS((TRIFLUOROMETHYL)SULFONYL)METHYL)SULFINYL)-L,L,2,2,3,3,4,4,4-NONAFLUOROBUTANE
(56A) 249
7.5.2 BIS(SULFINYL) C-H
ACIDS............................................................................................................257
RACEMIC
1,1,1,2,2,3,3,4,4-NONAFLUORO-4-((((TRIFLUOROMETHYL)SULFONYL)METHYL)SULFINYL)BUTANE
(148).................257
ENANTIOENRICHED
(R)-1,1,1,2,2,3,3,4,4-NONAFLUORO-4-((((TRIFLUOROMETHYL)SULFONYL)METHYL)SULFINYL)BUTANE
(148A)
................................................................................................................................................................................
258
ENANTIOPURE 2,2,6,6-TETRAMETHYLPIPERIDIN-1 -IUM (R,R)-
BIS((PERFLUOROBUTYL)SULFINYL)((TRIFLUOROMETHYL)SULFONYL)METHANIDE
(150)............................................................260
7.6 S
YNTHESIS
OF
D
IACID
26
......................................................................................................................
262
1,1,3,3-TETRA(TRIFLYL)PROPAN
(26)............................................................................................................................
262
7.7 S
YNTHESIS
OF
S
ILYL
K
ETENE
A
CETAL
8 0
...........................................................................................
263
FERF-BUTYL(( 1 -METHOXYVINYL)OXY)DIMETHYLSILANE
(80)...........................................................................................
263
7.8 R
EACT
IR S
TUDIES
..................................................................................................................................
264
7.9 M
UKAIYAMA
A
LDOL
R
EACTION
...........................................................................................................268
7.10 H
OSOMI
- S
AKURAI
R
EACTION
.............................................................................................................
271
7.11 F
RIEDEL
-C
RAFTS
A
CYLATION
............................................................................................................273
7.12
L O W CATALYST
LOADING.......................................................................................................................................
275
7.13 H
ETERO
-D
IELS
-A
LDER
R
EACTION
....................................................................................................
276
8
BIBLIOGRAPHY...........................................................................................................................................
278
9
APPENDIX......................................................................................................................................................
283
9.1 E
RKLAERUNG
/D
ECLARATION
.................................................................................................................
283
9.2 L
EBENSLAUF
/C V
...................................................................................................................................
285
|
| any_adam_object | 1 |
| author | Höfler, Denis 1989- |
| author_GND | (DE-588)1165183900 |
| author_facet | Höfler, Denis 1989- |
| author_role | aut |
| author_sort | Höfler, Denis 1989- |
| author_variant | d h dh |
| building | Verbundindex |
| bvnumber | BV045423451 |
| ctrlnum | (OCoLC)1090100477 (DE-599)DNB1169447422 |
| discipline | Chemie / Pharmazie |
| format | Thesis Book |
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| genre | (DE-588)4113937-9 Hochschulschrift gnd-content |
| genre_facet | Hochschulschrift |
| id | DE-604.BV045423451 |
| illustrated | Illustrated |
| indexdate | 2024-07-10T08:17:45Z |
| institution | BVB |
| language | English |
| oai_aleph_id | oai:aleph.bib-bvb.de:BVB01-030809295 |
| oclc_num | 1090100477 |
| open_access_boolean | |
| owner | DE-355 DE-BY-UBR DE-29T DE-83 |
| owner_facet | DE-355 DE-BY-UBR DE-29T DE-83 |
| physical | IX, 286 Seiten Illustrationen 21 cm |
| publishDate | 2018 |
| publishDateSearch | 2018 |
| publishDateSort | 2018 |
| record_format | marc |
| spelling | Höfler, Denis 1989- Verfasser (DE-588)1165183900 aut Highly active C-H acids for catalysis design and application vorgelegt von Denis Höfler aus Tettnang Köln 2018 IX, 286 Seiten Illustrationen 21 cm txt rdacontent n rdamedia nc rdacarrier Dissertation Universität zu Köln 2018 Kohlenstoff-Wasserstoff-Bindung (DE-588)4844082-6 gnd rswk-swf Katalyse (DE-588)4029921-1 gnd rswk-swf Organische Säuren (DE-588)4172774-5 gnd rswk-swf (DE-588)4113937-9 Hochschulschrift gnd-content Kohlenstoff-Wasserstoff-Bindung (DE-588)4844082-6 s Organische Säuren (DE-588)4172774-5 s Katalyse (DE-588)4029921-1 s DE-604 B:DE-101 application/pdf http://d-nb.info/1169447422/04 Inhaltsverzeichnis DNB Datenaustausch application/pdf http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=030809295&sequence=000001&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA Inhaltsverzeichnis |
| spellingShingle | Höfler, Denis 1989- Highly active C-H acids for catalysis design and application Kohlenstoff-Wasserstoff-Bindung (DE-588)4844082-6 gnd Katalyse (DE-588)4029921-1 gnd Organische Säuren (DE-588)4172774-5 gnd |
| subject_GND | (DE-588)4844082-6 (DE-588)4029921-1 (DE-588)4172774-5 (DE-588)4113937-9 |
| title | Highly active C-H acids for catalysis design and application |
| title_auth | Highly active C-H acids for catalysis design and application |
| title_exact_search | Highly active C-H acids for catalysis design and application |
| title_full | Highly active C-H acids for catalysis design and application vorgelegt von Denis Höfler aus Tettnang |
| title_fullStr | Highly active C-H acids for catalysis design and application vorgelegt von Denis Höfler aus Tettnang |
| title_full_unstemmed | Highly active C-H acids for catalysis design and application vorgelegt von Denis Höfler aus Tettnang |
| title_short | Highly active C-H acids for catalysis |
| title_sort | highly active c h acids for catalysis design and application |
| title_sub | design and application |
| topic | Kohlenstoff-Wasserstoff-Bindung (DE-588)4844082-6 gnd Katalyse (DE-588)4029921-1 gnd Organische Säuren (DE-588)4172774-5 gnd |
| topic_facet | Kohlenstoff-Wasserstoff-Bindung Katalyse Organische Säuren Hochschulschrift |
| url | http://d-nb.info/1169447422/04 http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=030809295&sequence=000001&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA |
| work_keys_str_mv | AT hoflerdenis highlyactivechacidsforcatalysisdesignandapplication |
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