Catalytic regioselective hydroamination of alkenes and alkynes:
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| Main Author: | |
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| Format: | Thesis Electronic Software eBook |
| Language: | English |
| Published: |
2005
|
| Subjects: | |
| Online Access: | Inhaltsverzeichnis |
| Physical Description: | 1 CD-ROM; 12 cm 12 cm Beil. ([2] Bl.) |
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MARC
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| 100 | 1 | |a Khedkar, Vivek Tukaram |d 1976- |e Verfasser |0 (DE-588)13034172X |4 aut | |
| 245 | 1 | 0 | |a Catalytic regioselective hydroamination of alkenes and alkynes |c vorgelegt von Vivek Tukaram Khedkar |
| 264 | 1 | |c 2005 | |
| 300 | |a 1 CD-ROM; 12 cm |c 12 cm |e Beil. ([2] Bl.) | ||
| 336 | |b txt |2 rdacontent | ||
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| 502 | |a Rostock, Univ., Diss., 2005 | ||
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| 689 | 0 | 1 | |a Hydroaminierung |0 (DE-588)4749938-2 |D s |
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| 689 | 0 | 3 | |a Regioselektivität |0 (DE-588)4307782-1 |D s |
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| 943 | 1 | |a oai:aleph.bib-bvb.de:BVB01-015611040 | |
Record in the Search Index
| _version_ | 1808044577042464768 |
|---|---|
| adam_text |
TABLE
OF
CONTENTS
I
TABLES
OF
CONTENTS
1.
INTRODUCTION.
.
1
K
HYDRO
AMIN
A
TION
OF
ALKENES
AND
ALKYNES
-
STA
TE
OF
THE
ART
4
2.1.
A
MINE
AND
THEIR
APPLICA
TIONS
.
4
2.2.
V
ARIOUS
ROUTES
TO
AMINES
.
5
2.3.
H
YDROAMINA
TION
-
T
HE
CHEMISTR
Y
.
7
2.3.1.
THERMODYNAMIC
AND
KINETIC
CONSIDERATIONS
.
8
2.3.2.
ACTIVATION
MECHANISM
.
9
2.3.2.1.
AMINE
ACTIVATION
.
9
2.3.2.2.
ACTIVATION
OF
C-C
MULTIPLE
BONDS
.
10
2.3.3.
REGIOCHEMISTRY
OF
HYDROAMINATION
.
11
2.4.
H
YDROAMINA
TION
OF
ALKENES
.
12
2.4.1.
LANTHANIDE
CATALYSTS
FOR
HYDROAMINATION
.
12
2.4.2.
TRANSITION
METAL
CATALYSTS
FOR
THE
HYDROAMINATION
OF
ALKENES
.
14
2.4.2.1.
RHODIUM-CATALYZED
HYDROAMINATION
.
14
2.4.2.2.
IRIDIUM
CATALYZED
HYDROAMINATION
.
16
2.4.2.3.
PALLADIUM-CATALYZED
HYDROAMINATION
.
17
2.4.3.
ALKALI
METAL
AND
BASE
CATALYSTS
FOR
HYDROAMINATION
.
17
2.4.3.1.
HYDROAMINATION
OF
ALIPHATIC
OLEFINS
.
18
2.4.3.1.1
HYDROAMINATION
OF
ETHYLENE
.
18
2.4.3.1.2
HYDROAMINATION
OF
HIGHER
ALKENES
.
21
2.4.3.2.
HYDROAMINATION
OF
AROMATIC
OLEFINS
.
23
2.4.3.3.
MECHANISM
FOR
THE
BASE-CATALYZED
HYDROAMINATION
.
26
3.
THEME
OF
THE
WORK
.
29
4.
BASE-CA
TALYZED
HYDROAMINA
TION
OF
ETHYLENE.
30
4.1.
B
ACKGROUND
.
30
4.2.
O
WN
RESULTS
.
31
4.2.1.
OPTIMIZATION
OF
REACTION
CONDITIONS
.
31
4.2.1.1.
SOLVENT
EFFECT
.
31
4.2.1.2.
EFFECT
OF
CATALYST
AND
TMEDA
CONCENTRATIONS
.
32
4.2.1.3.
TEMPERATURE
EFFECT
.
32
4.2.1.4.
EFFECT
OF
PRESSURE
AND
TIME
.
33
4.2.2.
SYNTHESIS
OF
LIGANDS
AND
SCREENING
OF
LIGANDS
.
34
4.2.3.
MECHANISTIC
CONSIDERATIONS
.
36
4.2.3.1.
LITHIUM
NMR
SPECTROSCOPY
.
38
4.2.3.2.
DEUTERIATED
13
C
NMR
SPECTROSCOPY.
39
5.
BASE-CA
TALYZED
HYDROAMINA
TION
OF
HIGHER
OLEFINS.
.
42
5.1.
I
NTRODUCTION
.
42
5.2.
R
ESULT
AND
DISCUSSION
.
42
5.2.1.
OPTIMIZATION
OF
REACTION
CONDITIONS
.
42
TABLE
OF
CONTENTS
5.2.2.
SCREENING
OF
THE
CATALYSTS.
45
5.2.3.
SELECTIVITY
EXPERIMENTS
.
46
REGIOSELECTIVE
INTERMOLECULAR
HYDROAMINATION
OF
ALKYNES
.48
6.1.
H
ISTORICAL
BACKGROUND
.
48
6.1.1.
MERCURY
AND
THALLIUM
COMPOUNDS
AS
HYDROAMINATION
CATALYSTS
.
48
6.1.2.
LANTHANIDE
AND
ACTINIDE
COMPLEXES
AS
HYDROAMINATION
CATALYSTS
.
49
6.1.3.
BASE-CATALYZED
HYDROAMINATION
OF
ALKYNES
.
50
6.1.4.
LATE
TRANSITION
METAL
COMPLEX
CATALYZED
HYDROAMINATION
OF
ALKYNES
.
51
6.1.5.
EARLY
TRANSITION
METAL
COMPLEXES
CATALYZED
HYDROAMINATION
OF
ALKYNES
.
55
6.1.5.1.
ZIRCONIUM
COMPLEXES.
55
6.1.5.2.
TITANIUM
COMPLEXES
AS
CATALYSTS
FOR
THE
HYDROAMINATION
.
56
6.2.
THE
ARYLOXOTITANIUM
COMPLEX-CATALYZED
HYDROAMINATION
OF
ALKYNES.
65
6.2.1.
RESULTS
.
65
6.2.2.
MODEL
REACTION
.66
6.2.3.
SCOPE
AND
LIMITATION
.
67
6.2.4.
HYDROAMINATION
OF
INTERNAL
ALKYNES
.
73
6.3.
MONODENTA
TE
AND
BIDENTA
TE
ARYLOXO
LIGANDS
IN
HYDROAMINA
TION
OF
ALKYNES
.
73
6.3.1.
MONODENTATE
ALKYL
AND
ARYLOXO
LIGANDS
.
74
6.3.1.1.
EFFECT
OF
DIFFERENT
AMINES
.
76
6.3.2.
BIDENTATE
ALKYL
AND
ARYLOXO
LIGANDS
.
78
6.3.3.
COMPARISON
OF
CATALYTIC
SYSTEMS
.
80
6.3.4.
INFLUENCE
OF
THE
TITANIUM
TO
LIGAND
RATIO
.
81
6.3.5.
INTERNAL
ALKYNE
HYDROAMINATION
.
83
6.3.6.
SCOPE
OF
THE
REACTION
.
83
6.4.
T
HEORETICAL
CALCULATIONS
ON
THE
ARYLOXOTITANIUM
-
CATALYZED
HYDROAMINATION
OF
TERMINAL
ALKYNES
.
86
SYNTHESIS
OF
INDOLES
VIA
CATALYTIC
HYDROAMINATION.
.
93
7.1.
I
NTRODUCTION
.
93
7.1.1.
METHODS
FOR
SYNTHESIS
OF
INDOLES
.
94
7.1.1.1.
FISHER
INDOLE
SYNTHESIS
.
94
7.1.1.2.
LATE
TRANSITION
METAL
CATALYZED
INDOLE
SYNTHESIS
.
95
7.1.1.3.
EARLY
TRANSITION
METAL
CATALYZED
INDOLE
SYNTHESIS
.
97
7.
2.
S
YNTHESIS
OF
TR
YPTAMINES
AND
HOMOTR
YPTAMINES
.
99
7.2.1.
INITIAL
OPTIMIZATION
OF
THE
NEW
DOMINO
REACTION
.
99
7.2.2.
SCOPE
OF
THE
NEW
DOMINO
REACTION
.
101
7.3.
S
YNTHESIS
OF
TRYPTOPHOLS
.
105
7.3.1.
OPTIMIZATION
OF
ONE-POT
PROCEDURE
.
106
7.3.2.
SYNTHESIS
OF
DIFFERENT
TRYPTOPHOLS
.
108
SUMMARY
.
113
EXPERIMENTAL
SECTION.
.
118
TABLE
OF
CONTENTS
III
9.1.
G
ENERAL
REAGENTS
.
118
9.1.1.
A
NALYTICS
.
118
9.1.2.
REACTION
EQUIPMENT
.
119
9.2.
G
ENERAL
PROCEDURE
FOR
BASE
-
CATALYZED
HYDRO
AMINATION
OF
ETHYLENE
(GPI)
.
119
9.2.1.
SYNTHESIS
OF
DIAMINE
LIGANDS
.
120
9.3.
G
ENERAL
PROCEDURE
FOR
BASE
-
CA
TALYZED
HYDROAMINA
TION
OF
HIGHER
OLEFINS
(GP
III)
.
121
9.4.
S
YNTHESIS
OF
COMPLEX
[T
I
(NM
E
2)2(OA
R
)
2
](A
R
=
4-M
ETHYL
-2,6
DI
-
TERT
-
BUTYLPHENOLATE
)
(1)
.
122
9.5.
G
ENERAL
PROCEDURE
FOR
THE
HYDROAMINA
TION
OF
ALKYNES
(GP
IV)
.
122
9.6.
G
ENERAL
PROCEDURE
FOR
THE
SYNTHESIS
OF
IMINES
(GP
V).
135
9.
7.
G
ENERAL
PROCEDURE
FOR
THE
SYNTHESIS
OF
TRYPTAMINES
(GP
VI)
.
141
9.8.
G
ENERAL
PROCEDURE
FOR
SYNTHESIS
OF
TR
YPTOPHOLS
(GP
VII)
.
153
10.
REFERENCES
.
173 |
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| index_date | 2024-07-02T17:18:49Z |
| indexdate | 2024-08-22T00:14:33Z |
| institution | BVB |
| language | English |
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| spelling | Khedkar, Vivek Tukaram 1976- Verfasser (DE-588)13034172X aut Catalytic regioselective hydroamination of alkenes and alkynes vorgelegt von Vivek Tukaram Khedkar 2005 1 CD-ROM; 12 cm 12 cm Beil. ([2] Bl.) txt rdacontent c rdamedia cd rdacarrier Rostock, Univ., Diss., 2005 Katalyse (DE-588)4029921-1 gnd rswk-swf Hydroaminierung (DE-588)4749938-2 gnd rswk-swf Regioselektivität (DE-588)4307782-1 gnd rswk-swf Alkine (DE-588)4141897-9 gnd rswk-swf Alkene (DE-588)4001207-4 gnd rswk-swf (DE-588)4113937-9 Hochschulschrift gnd-content Alkene (DE-588)4001207-4 s Hydroaminierung (DE-588)4749938-2 s Katalyse (DE-588)4029921-1 s Regioselektivität (DE-588)4307782-1 s DE-604 Alkine (DE-588)4141897-9 s DNB Datenaustausch application/pdf http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=015611040&sequence=000001&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA Inhaltsverzeichnis |
| spellingShingle | Khedkar, Vivek Tukaram 1976- Catalytic regioselective hydroamination of alkenes and alkynes Katalyse (DE-588)4029921-1 gnd Hydroaminierung (DE-588)4749938-2 gnd Regioselektivität (DE-588)4307782-1 gnd Alkine (DE-588)4141897-9 gnd Alkene (DE-588)4001207-4 gnd |
| subject_GND | (DE-588)4029921-1 (DE-588)4749938-2 (DE-588)4307782-1 (DE-588)4141897-9 (DE-588)4001207-4 (DE-588)4113937-9 |
| title | Catalytic regioselective hydroamination of alkenes and alkynes |
| title_auth | Catalytic regioselective hydroamination of alkenes and alkynes |
| title_exact_search | Catalytic regioselective hydroamination of alkenes and alkynes |
| title_exact_search_txtP | Catalytic regioselective hydroamination of alkenes and alkynes |
| title_full | Catalytic regioselective hydroamination of alkenes and alkynes vorgelegt von Vivek Tukaram Khedkar |
| title_fullStr | Catalytic regioselective hydroamination of alkenes and alkynes vorgelegt von Vivek Tukaram Khedkar |
| title_full_unstemmed | Catalytic regioselective hydroamination of alkenes and alkynes vorgelegt von Vivek Tukaram Khedkar |
| title_short | Catalytic regioselective hydroamination of alkenes and alkynes |
| title_sort | catalytic regioselective hydroamination of alkenes and alkynes |
| topic | Katalyse (DE-588)4029921-1 gnd Hydroaminierung (DE-588)4749938-2 gnd Regioselektivität (DE-588)4307782-1 gnd Alkine (DE-588)4141897-9 gnd Alkene (DE-588)4001207-4 gnd |
| topic_facet | Katalyse Hydroaminierung Regioselektivität Alkine Alkene Hochschulschrift |
| url | http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=015611040&sequence=000001&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA |
| work_keys_str_mv | AT khedkarvivektukaram catalyticregioselectivehydroaminationofalkenesandalkynes |