SUCCESS2016-08-10T22:58:56.93500991a34bdb-ba93-4833-b344-91857404f3f2- ClC=1C=CC(=NC1C1=CC=CC=C1)C(=O)OC(C)C
- 1
- isopropyl 5-chloro-6-phenylpicolinate
- FC=1C=CC(=NC1C1=CC=CC=C1)C(=O)OC(C)C
- 2
- Isopropyl 5-Fluoro-6-phenylpicolinate
- product
- 3a
- compounds
- [N+](=O)([O-])C1=C(C#N)C=CC=C1
- 3d
- 2-Nitrobenzonitrile
- 2-nitrobenzonitrile
- FC1=C(C#N)C=CC=C1
- 4
- 2-Fluorobenzonitrile
- product
- FC(S(=O)(=O)OC1=NC=CC=C1)(F)F
- 5e
- Pyridin-2-yl trifluoromethanesulfonate
- FC=1C=CC(=NC1C1=CC=C(C=C1)Cl)C(=O)OC(C)C
- °C73–76
- 7
- Isopropyl 5-Fluoro-6-(p-chlorophenyl)picolinate
- product
- FC=1C=CC(=NC1C1=CC=C(C=C1)OC)C(=O)OC(C)C
- °C46–48
- 8
- Isopropyl 5-Fluoro-6-(p-methoxyphenyl)picolinate
- product
- FC1=CC(=NC(=C1F)C1=CC=CC=C1)C(=O)OC(C)C
- 9
- Isopropyl 4,5-Difluoro-6-phenylpicolinate
- FC1=CC(=NC(=C1F)C1=CC=C(C=C1)Cl)C(=O)OC(C)C
- °C74–76
- 10
- Isopropyl 4,5-Difluoro-6-(p-chlorophenyl)picolinate
- product
- FC1=CC(=NC(=C1F)C1=CC=C(C=C1)OC)C(=O)OC(C)C
- °C37–38
- 11
- Isopropyl 4,5-Difluoro-6-(p-methoxyphenyl)picolinate
- product
- FC1=NC2=CC=CC=C2C=C1
- 12
- 2-Fluoroquinoline
- FC1=CC=NC2=CC(=CC=C12)C(F)(F)F
- °C84–86
- 13
- 4-Fluoro-7-(trifluoromethyl)quinoline
- product
- FC1=NC=CC2=CC=CC=C12
- 14
- 1-Fluoroisoquinoline
- C(C1=CC=CC=C1)OC=1C=CC=C2C=CC(=NC12)F
- °C67–69
- CDCl3125.7513C
- 161.5Hz242d
- 153.4
- 142.0Hz9.5d
- 138.7
- 137.6Hz15.3d
- 136.8
- 128.6
- 128.0Hz1.9d
- 127.0
- 126.9
- 126.1Hz2.9d
- 119.6
- 111.6
- 110.6Hz42.9d
- 70.7
MHz - product
- 15
- 8-(benzyloxy)-2-fluoroquinoline
- 8-(Benzyloxy)-2-fluoroquinoline
- FC=1N=NC(=CC1)C1=CC=CC=C1
- cm–11584
- cm–11556
- cm–11450
- cm–11427
- cm–11278
- cm–11108
- cm–1852
- cm–1778
- cm–1739
- CDCl310019F
- –84.8Hz1.5d
MHz - CDCl35001H
- 8.01–7.983Hmultiple peaks
- 7.53–7.493Hmultiple peaks
- 7.29Hzdd1H9.5 , 2.0
MHz - CDCl3175.9513C
- 166.7Hz245d
- 159.2Hz3.5d
- 135.1Hz2.1d
- 130.2
- 129.5Hz7.6d
- 129.0
- 127.0
- 116.1Hz33.4d
MHz - 16
- °C129–131
- 3-Fluoro-6-phenylpyridazine
- FC1=NC=CC=C1C(F)(F)F
- 17
- 2-Fluoro-3-(trifluoromethyl)pyridine
- FC1=NC=C(C=C1)C(F)(F)F
- 18
- 2-Fluoro-5-(trifluoromethyl)pyridine
- FC1=NC=CC(=C1)C#N
- 19
- 2-Fluoro-4-cyanopyridine
- FC1=NC=CC=C1C#N
- 20
- 2-Fluoro-3-cyanopyridine
- FC1=NC=C(C=C1)C#N
- 21
- 2-Fluoro-5-cyanopyridine
- FC1=NC=CN=C1
- 22
- 2-Fluoropyrazine
- FC1=NC=CC=C1Cl
- 23
- 2-Fluoro-3-chloropyridine
- FC1=NC=C(C=C1)I
- 24
- 2-Fluoro-5-iodopyridine
- FC1=NC=C(C=C1)[N+](=O)[O-]
- 25
- 2-Fluoro-5-nitropyridine
- FC1=NC=C(C=C1)Br
- 26
- 2-Fluoro-5-bromopyridine
- FC1=NC(=CC=C1)F
- 27
- 2,6-Difluoropyridine
- FC=1C=C(C#N)C=CC1
- 28
- 3-fluorobenzonitrile
- 3-Fluorobenzonitrile
- product
- FC1=CC=C(C#N)C=C1
- 29
- 4-Fluorobenzonitrile
- FC1=CC=C(C(=O)OCC)C=C1
- 30
- Ethyl 4-Fluorobenzoate
- FC1=CC=C(C(=O)C2=CC=CC=C2)C=C1
- °C47–48
- 31
- 4-Fluorobenzophenone
- NHCs
- N - heterocyclic carbenes
- N-heterocyclic carbenes
- [C-]#N.C(CCC)[N+](CCCC)(CCCC)CCCC
- tetrabutylammonium cyanide
- TBACN
- alkali metal fluorides
- MF
- [F-]
- fluoride
- Fluoride
- [F-].C[N+](C)(C)C
- tetramethylammonium fluoride
- Tetramethylammonium Fluoride
- pp 12137–12145
- aryl-F
- arenes
- Fluorinated arenes
- heteroarenes
- [H]*
- hydrogen
- CF
- C–F
- heteroaryl fluorides
- (hetero)aryl halide
- DiMagno
- [F-].C(CCC)[N+](CCCC)(CCCC)CCCC
- tetrabutylammonium fluoride
- FC1=C(C(=C(C(=C1F)F)F)F)F
- hexafluorobenzene
- Cl*
- chloro-
- fluorides
- acyl azolium fluorides
- NMe4Cl
- NMe4OH
- fluoroarene
- phenols
- aryl fluorides
- chloropicolinates
- (hetero)aromatic
- ClC=1C=CC(=NC1)C(=O)[O-]
- 5-chloropicolinate
- FC=1C(=NC=CC1)C(=O)[O-]
- fluoropicolinate
- carboxylic acid
- 2-CO2H
- isopropyl ether 1-iPrO
- CF
- CH3F
- acyl azolium fluoride
- NMe4F·4H2O
- O
- H2O
- F[H-]F
- Bifluoride
- CH2Cl2
- 2-substituted-benzonitrile substrates
- aryl iodides
- N(=O)[O-]
- nitrite
- 2-chloro
- 2-bromo
- 2-iodo
- FC1=NC=CC=C1
- 2-fluoropyridine
- product
- (hetero)aryl triflates
- [O-]S(=O)(=O)C(F)(F)F
- triflate
- BrC1=NC=CC=C1
- 2-bromopyridine
- 2-halopyridines
- monochloropicolinates
- dichloropicolinates
- ClC1=C(C(=NC=C1)C(=O)[O-])Cl
- dichloropicolinate
- [Cl-]
- chloride
- Chloroquinoline, chloroisoquinoline
- ClC=1N=NC=CC1
- chloropyridazine
- Methoxy, cyano
- FC(F)(F)*
- trifluoromethyl
- 2- and 4-fluorobenzonitrile
- ClC1=CC=C(C(=O)OCC)C=C1
- ethyl 4-chlorobenzoate
- ClC1=CC=C(C(=O)C2=CC=CC=C2)C=C1
- 4-chlorobenzophenone
- 3–10-fold
- 1H and 13C
- 1H δ
- c1ccc(cc1)c2ccccc2
- diphenyl
- dimethyl polysiloxane
- [He]
- Helium
- CN(C=O)C
- N,N-dimethylformamide
- Isopropyl chloroarylpicolinates
- 2-Cyanophenyl trifluoromethanesulfonate, pyridine-2-yl trifluoromethanesulfonate
- P2O5
- N#N
- N2
- S(=O)(=O)([O-])[O-].[Mg+2]
- magnesium sulfate
- O=[Si]=O
- silica gel
- C(C)OCC
- diethyl ether
- C15H15FNO2
- [N]
- nitrogen
- O=[Si]=O
- Silica
- ClC=1C=CC(=NC1C1=CC=C(C=C1)Cl)C(=O)OC(C)C
- isopropyl 5-chloro-6-(p-chlorophenyl)picolinate
- C15H14ClFNO2
- ClC=1C=CC(=NC1C1=CC=C(C=C1)OC)C(=O)OC(C)C
- isopropyl 5-chloro-6-(p-methoxyphenyl)picolinate
- C16H17FNO3
- ClC1=CC(=NC(=C1Cl)C1=CC=CC=C1)C(=O)OC(C)C
- isopropyl 4,5-dichloro-6-phenylpicolinate
- C15H14F2NO2
- ClC1=CC(=NC(=C1Cl)C1=CC=C(C=C1)Cl)C(=O)OC(C)C
- isopropyl 4,5-dichloro-6-(p-chlorophenyl)picolinate
- C15H13ClF2NO2
- ClC1=CC(=NC(=C1Cl)C1=CC=C(C=C1)OC)C(=O)OC(C)C
- isopropyl 4,5-dichloro-6-(p-methoxyphenyl)picolinate
- C16H16F2NO3
- ClC1=NC2=CC=CC=C2C=C1
- 2-chloroquinoline
- ClC1=CC=NC2=CC(=CC=C12)C(F)(F)F
- 4-chloro-7-(trifluoromethyl)quinoline
- ClC1=NC=CC2=CC=CC=C12
- 1-chloroisoquinoline
- 3-chloro-6-phenylpyridzaine
- ClC1=NC=CC=C1C(F)(F)F
- 2-chloro-3-(trifluoromethyl)pyridine
- ClC1=NC=C(C=C1)C(F)(F)F
- 2-chloro-5-(trifluoromethyl)pyridine
- ClC1=NC=CC(=C1)C#N
- 2-chloro-4-cyanopyridine
- ClC1=NC=CC=C1C#N
- 2-chloro-3-cyanopyridine
- ClC1=NC=C(C=C1)C#N
- 2-chloro-5-cyanopyridine
- ClC1=NC=CN=C1
- 2-chloropyrazine
- [N+](=O)([O-])C1=NC=CC=C1Cl
- 2-nitro-3-chloropyridine
- ClC1=NC=C(C=C1)I
- 2-chloro-5-iodopyridine
- ClC1=NC=C(C=C1)[N+](=O)[O-]
- 2-chloro-5-nitropyridine
- ClC1=NC=C(C=C1)Br
- 2-chloro-5-bromopyridine
- ClC1=NC(=CC=C1)Cl
- 2,6-dichloropyridine
- ClC1=C(C#N)C=CC=C1
- 2-chlorobenzonitrile
- ClC=1C=C(C#N)C=CC1
- 3-chlorobenzonitrile
- ClC1=CC=C(C#N)C=C1
- 4-chlorobenzonitrile
- [N+](=O)([O-])C1=CC=C(C(=O)OCC)C=C1
- ethyl 4-nitrobenzoate
- [N+](=O)([O-])C1=CC=C(C(=O)C2=CC=CC=C2)C=C1
- 4-nitrobenzophenone
- OTf
- [F]
- fluorine
- aryl
- product
- nitroarene
- aryl fluoride
- product
- C6F6
- aryl chlorides
- aryl triflate
- aryl bromides
- aryl ether
- 2-substituted pyridines
- [N+](=O)([O-])C1=NC=CC=C1
- 2-nitropyridine
- aryl bromide
- halide
- [N+](=O)([O-])*
- nitro
- C(C1=CC=CC=C1)OC=1C=CC=C2C=CC(=NC12)Cl
- 8-(benzyloxy)-2-chloroquinoline
- aryl chloride
- nitroarene substrate
- C(C)(=O)OCC
- ethyl acetate
- 1H
- [13CH4]
- 13C
- EtOAc
- aryl halides
- nitroarenes
- O=[N+]=O
- NO2
- Cl
- Cl
- Br
- Br
- ClCCl
- dichloromethane
- Teflon
- CDCl3
- C[S](C)=O
- DMSO
- FC1=CC(=CC(=C1)F)F
- 1,3,5-trifluorobenzene
- C1(=CC=CC=C1)C
- toluene
- CN(C)C=O
- DMF
- Et2O
- 1H, 13C
- [ M + H]+ calcd
- CCCCCC
- hexanes
- CC(=O)N[C@@H]1[C@@H](O)[C@@H](F)C(O[C@H]1[C@H](O)[C@H](O)CO)(O[P](O)(=O)OC[C@H]2O[C@H]([C@H](O)[C@@H]2O)N3C=CC(=NC3=O)N)C(O)=O
- CsF
- 19F
- NMe4F
- nitroarenes
- using
- anhydrous
- tetramethylammonium
- fluoride
- anh
- anhydrous
- TBACN
- tetrabutylammonium
- cyanide
- CM
- NHCs
- N
- -
- heterocyclic
- carbenes
- CM
- anh
- and
- Marshall
- have
- reported
- that
- NMe4F
- i.e
- initially
- examined
- at
- 140
- °
- C
- COM
- cost
- of
- manufacturing
- anh
- and
- 5d
- with
- CsF
- and
- NMe4F
- anh
- and
- nitroarenes
- react
- with
- NMe4F
- anh
- analysis
- projects
- that
- NMe4F
- ppm
- parts
- per
- million
American Chemical Society10.1021/acs.joc.5b02075Anhydrous Tetramethylammonium Fluoride for Room-Temperature SNAr Fluorination2015-12-09T00:00:0091a34bdb-ba93-4833-b344-91857404f3f2.html- Sydonie D. Schimler
- Sarah J. Ryan
- Douglas C. Bland
- John E. Anderson
- Melanie S. Sanford