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[ CAS No. 175676-42-3 ] {[proInfo.proName]}

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Cat. No.: {[proInfo.prAm]}
3d Animation Molecule Structure of 175676-42-3
Chemical Structure| 175676-42-3
Chemical Structure| 175676-42-3
Structure of 175676-42-3 * Storage: {[proInfo.prStorage]}
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Product Details of [ 175676-42-3 ]

CAS No. :175676-42-3 MDL No. :MFCD31695793
Formula : C8H7F3O3S Boiling Point : -
Linear Structure Formula :- InChI Key :NHBKFPDJMAEDOS-UHFFFAOYSA-N
M.W : 240.20 Pubchem ID :13494930
Synonyms :

Calculated chemistry of [ 175676-42-3 ]

Physicochemical Properties

Num. heavy atoms : 15
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.25
Num. rotatable bonds : 3
Num. H-bond acceptors : 6.0
Num. H-bond donors : 0.0
Molar Refractivity : 45.78
TPSA : 51.75 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : Yes
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.79 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.12
Log Po/w (XLOGP3) : 2.78
Log Po/w (WLOGP) : 4.56
Log Po/w (MLOGP) : 2.25
Log Po/w (SILICOS-IT) : 1.74
Consensus Log Po/w : 2.69

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 0.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -3.18
Solubility : 0.159 mg/ml ; 0.000663 mol/l
Class : Soluble
Log S (Ali) : -3.52
Solubility : 0.0721 mg/ml ; 0.0003 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.34
Solubility : 0.109 mg/ml ; 0.000454 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.15

Safety of [ 175676-42-3 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P280-P301+P312-P302+P352-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 175676-42-3 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 175676-42-3 ]

[ 175676-42-3 ] Synthesis Path-Downstream   1~92

  • 1
  • [ 175676-42-3 ]
  • [ 14330-41-7 ]
  • 2-(4-(trifluoromethoxy)butyl)thiophene [ No CAS ]
YieldReaction ConditionsOperation in experiment
71% With tetramethylammonium bromide; cesium fluoride In N,N,N,N,N,N-hexamethylphosphoric triamide; N,N-dimethyl acetamide at 30 - 100℃; for 26h; Inert atmosphere; Sealed tube;
  • 2
  • [ 175676-42-3 ]
  • [ 883-44-3 ]
  • 2-[3-(trifluoromethoxy)propyl]-1H-isoindole-1,3(2H)-dione [ No CAS ]
  • 3
  • [ 175676-42-3 ]
  • [ 3360-41-6 ]
  • (4-(trifluoromethoxy)butyl)benzene [ No CAS ]
YieldReaction ConditionsOperation in experiment
83% With tetramethylammonium bromide; cesium fluoride In N,N,N,N,N,N-hexamethylphosphoric triamide; N,N-dimethyl acetamide at 30 - 100℃; for 26h; Inert atmosphere; Sealed tube;
  • 4
  • [ 175676-42-3 ]
  • [ 52244-70-9 ]
  • 1-methoxy-4-(4-(trifluoromethoxy)butyl)benzene [ No CAS ]
YieldReaction ConditionsOperation in experiment
83% With tetramethylammonium bromide; cesium fluoride In N,N,N,N,N,N-hexamethylphosphoric triamide; N,N-dimethyl acetamide at 30 - 100℃; for 26h; Inert atmosphere; Sealed tube;
  • 5
  • [ 175676-42-3 ]
  • [ 2430-16-2 ]
  • 6-(trifluoromethoxy)-1-phenylhexane [ No CAS ]
YieldReaction ConditionsOperation in experiment
83% With tetramethylammonium bromide; cesium fluoride In N,N,N,N,N,N-hexamethylphosphoric triamide; N,N-dimethyl acetamide at 30 - 100℃; for 26h; Inert atmosphere; Sealed tube;
  • 6
  • [ 175676-42-3 ]
  • [ 1454-85-9 ]
  • 1-(trifluoromethoxy)heptadecane [ No CAS ]
  • 7
  • [ 175676-42-3 ]
  • [ 1504-58-1 ]
  • (3-(trifluoromethoxy)prop-1-yn-1-yl)benzene [ No CAS ]
YieldReaction ConditionsOperation in experiment
69% With tetramethylammonium bromide; cesium fluoride In N,N,N,N,N,N-hexamethylphosphoric triamide; N,N-dimethyl acetamide at 60℃; for 26h; Inert atmosphere; Sealed tube;
  • 8
  • [ 175676-42-3 ]
  • [ 4407-36-7 ]
  • [ 1241960-07-5 ]
YieldReaction ConditionsOperation in experiment
71% With tetramethylammonium bromide; cesium fluoride In N,N,N,N,N,N-hexamethylphosphoric triamide; N,N-dimethyl acetamide at 40℃; for 26h; Inert atmosphere; Sealed tube;
  • 9
  • [ 175676-42-3 ]
  • [ 873-76-7 ]
  • 1-chloro-4-((trifluoromethoxy)methyl)benzene [ No CAS ]
YieldReaction ConditionsOperation in experiment
57% With tetramethylammonium bromide; cesium fluoride In N,N,N,N,N,N-hexamethylphosphoric triamide; N,N-dimethyl acetamide at 70℃; for 26h; Inert atmosphere; Sealed tube;
  • 10
  • [ 175676-42-3 ]
  • [ 873-75-6 ]
  • 1-bromo-4-((trifluoromethoxy)methyl)benzene [ No CAS ]
YieldReaction ConditionsOperation in experiment
61% With tetramethylammonium bromide; cesium fluoride In N,N,N,N,N,N-hexamethylphosphoric triamide; N,N-dimethyl acetamide at 70℃; for 26h; Inert atmosphere; Sealed tube;
  • 11
  • [ 175676-42-3 ]
  • [ 18282-51-4 ]
  • 1-iodo-4-((trifluoromethoxy)methyl)benzene [ No CAS ]
YieldReaction ConditionsOperation in experiment
79% With tetramethylammonium bromide; cesium fluoride In N,N,N,N,N,N-hexamethylphosphoric triamide; N,N-dimethyl acetamide at 70℃; for 26h; Inert atmosphere; Sealed tube;
  • 12
  • [ 175676-42-3 ]
  • [ 3597-91-9 ]
  • 4-((trifluoromethoxy)methyl)-1,1'-biphenyl [ No CAS ]
YieldReaction ConditionsOperation in experiment
87% With tetramethylammonium bromide; cesium fluoride In N,N,N,N,N,N-hexamethylphosphoric triamide; N,N-dimethyl acetamide at 70℃; for 26h; Inert atmosphere; Sealed tube;
  • 13
  • [ 175676-42-3 ]
  • [ 877-65-6 ]
  • 1-(tert-butyl)-4-((trifluoromethoxy)methyl)benzene [ No CAS ]
YieldReaction ConditionsOperation in experiment
83% With tetramethylammonium bromide; cesium fluoride In N,N,N,N,N,N-hexamethylphosphoric triamide; N,N-dimethyl acetamide at 70℃; for 26h; Inert atmosphere; Sealed tube;
  • 14
  • [ 175676-42-3 ]
  • [ 1736-74-9 ]
  • 1-trifluoromethoxy-4-((trifluoromethoxy)methyl)benzene [ No CAS ]
  • 15
  • [ 175676-42-3 ]
  • [ 874-89-5 ]
  • 4-((trifluoromethoxy)methyl)benzonitrile [ No CAS ]
  • 16
  • [ 175676-42-3 ]
  • [ 619-73-8 ]
  • [ 1174287-17-2 ]
YieldReaction ConditionsOperation in experiment
72% With tetramethylammonium bromide; cesium fluoride In N,N,N,N,N,N-hexamethylphosphoric triamide; N,N-dimethyl acetamide at 70℃; for 26h; Inert atmosphere; Sealed tube;
  • 17
  • [ 175676-42-3 ]
  • [ 349-95-1 ]
  • 1-((trifluoromethoxy)methyl)-4-(trifluoromethyl)benzene [ No CAS ]
YieldReaction ConditionsOperation in experiment
57% With tetramethylammonium bromide; cesium fluoride In N,N,N,N,N,N-hexamethylphosphoric triamide; N,N-dimethyl acetamide at 70℃; for 26h; Inert atmosphere; Sealed tube;
  • 18
  • [ 175676-42-3 ]
  • [ 6908-41-4 ]
  • [ 1006904-70-6 ]
YieldReaction ConditionsOperation in experiment
78% With tetramethylammonium bromide; cesium fluoride In N,N,N,N,N,N-hexamethylphosphoric triamide; N,N-dimethyl acetamide at 70℃; for 26h; Inert atmosphere; Sealed tube;
  • 19
  • [ 175676-42-3 ]
  • [ 4780-79-4 ]
  • 1-((trifluoromethoxy)methyl)naphthalene [ No CAS ]
YieldReaction ConditionsOperation in experiment
80% With tetramethylammonium bromide; cesium fluoride In N,N,N,N,N,N-hexamethylphosphoric triamide; N,N-dimethyl acetamide at 70℃; for 26h; Inert atmosphere; Sealed tube;
  • 20
  • [ 175676-42-3 ]
  • [ 3391-10-4 ]
  • 1-chloro-4-(1-(trifluoromethoxy)ethyl)benzene [ No CAS ]
YieldReaction ConditionsOperation in experiment
63% With tetraethylammonium bromide; cesium fluoride In N,N,N,N,N,N-hexamethylphosphoric triamide; N,N-dimethyl acetamide at 70℃; for 26h; Inert atmosphere; Sealed tube;
  • 21
  • [ 175676-42-3 ]
  • [ 5391-88-8 ]
  • 1-bromo-4-(1-(trifluoromethoxy)ethyl)benzene [ No CAS ]
YieldReaction ConditionsOperation in experiment
75% With tetraethylammonium bromide; cesium fluoride In N,N,N,N,N,N-hexamethylphosphoric triamide; N,N-dimethyl acetamide at 70℃; for 26h; Inert atmosphere; Sealed tube;
  • 22
  • [ 175676-42-3 ]
  • [ 2344-70-9 ]
  • 4-phenyl-2-(trifluoromethoxy)butane [ No CAS ]
YieldReaction ConditionsOperation in experiment
66% With tetraethylammonium bromide; cesium fluoride In N,N,N,N,N,N-hexamethylphosphoric triamide; N,N-dimethyl acetamide at 30 - 100℃; for 26h; Inert atmosphere; Sealed tube;
  • 23
  • [ 175676-42-3 ]
  • 1-naphthalenemethanol-[18O] [ No CAS ]
  • 1-((trifluoromethoxy)methyl)naphthalene [ No CAS ]
YieldReaction ConditionsOperation in experiment
69% With tetramethylammonium bromide; cesium fluoride In N,N,N,N,N,N-hexamethylphosphoric triamide; N,N-dimethyl acetamide at 70℃; for 26h; Inert atmosphere; Sealed tube;
  • 24
  • [ 175676-42-3 ]
  • [ 130-95-0 ]
  • (1R,6R,7R,8aS)-1-(6-methoxyquinolin-4-yl)-7-(2-(trifluoromethoxy)ethyl)-6-vinylhexahydro-3H-oxazolo[3,4-a]pyridin-3-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
55% With tetraethylammonium bromide; cesium fluoride In N,N,N,N,N,N-hexamethylphosphoric triamide; N,N-dimethyl acetamide at 30 - 100℃; for 26h; Inert atmosphere; Sealed tube;
  • 25
  • [ 175676-42-3 ]
  • 1-hydroxy-3-hydroxyethyladamantane [ No CAS ]
  • 1-hydroxy-3-(2-(trifluoromethoxy)ethyl)adamantane [ No CAS ]
YieldReaction ConditionsOperation in experiment
68% With tetramethylammonium bromide; cesium fluoride In N,N,N,N,N,N-hexamethylphosphoric triamide; N,N-dimethyl acetamide at 30 - 100℃; for 26h; Inert atmosphere; Sealed tube;
  • 26
  • [ 175676-42-3 ]
  • [ 2039-82-9 ]
  • 1-(2-azido-1-(trifluoromethoxy)ethyl)-4-bromobenzene [ No CAS ]
YieldReaction ConditionsOperation in experiment
38% With tris(2,2-bipyridine)ruthenium(II) hexafluorophosphate; silver fluoride; 1-azido-1λ3-benzo[d][1,2]iodaoxol-3(1H)-one; 4,4',4-tri-tert-butyl-2,2':6',2-terpyridine In acetonitrile at 10℃; for 4h; Inert atmosphere; Glovebox; Sealed tube; Irradiation;
38% With tris(2,2-bipyridine)ruthenium(II) hexafluorophosphate; silver fluoride; 1-azido-1λ3-benzo[d][1,2]iodaoxol-3(1H)-one; 4,4',4-tri-tert-butyl-2,2':6',2-terpyridine In acetonitrile at 20℃; for 4h; Inert atmosphere; Sealed tube; Irradiation; 68 Example 6 1-(2-azido-1-(trifluoromethoxy)ethyl)-2,4,6-trimethylbenzene (4a) General procedure: Under the protection of N2, Ru(bpy)3(PF6)2 (2.4 mg, 0.00300 mmol, 1.0 mol%), AgF (19.2 mg, 0.150 mmol, 50.0 mol%) was added to the sealed tube. 4,4',4"-tri-tert-butyl-2,2':6',2"-terpyridine (tbtpy, 36.0 mg, 0.0900 mmol, 30.0 mol%),1-azido-1,3 benzo[d][1,2]iodohydroxy-3(1H)-one (3) (173.4 mg, 0.600 mmol, 2.00 eq.), then acetonitrile solvent (2.40 mL) ,4-phenylstyrene (1a) (43.9 mg, 0.300 mmol, 1.00 equiv), trifluoromethyl 4-methylbenzenesulfonate (2) (169 μL, 0.9 mmol, 3.00 equiv) was added to the reaction. The resulting mixture was then allowed to stand at room temperature and stirred under irradiation with a 14 W blue LED for 4 hours.After that, the reaction mixture was concentrated in vacuo and purified by silica gel chromatography.Elution with petroleum ether / ethyl acetate 100:1 (v / v) gave the corresponding product (4a), 65.5mg.
  • 27
  • [ 175676-42-3 ]
  • [ 2351-50-0 ]
  • 1-(2-azido-1-(trifluoromethoxy)ethyl)-4-iodobenzene [ No CAS ]
YieldReaction ConditionsOperation in experiment
40% With tris(2,2-bipyridine)ruthenium(II) hexafluorophosphate; silver fluoride; 1-azido-1λ3-benzo[d][1,2]iodaoxol-3(1H)-one; 4,4',4-tri-tert-butyl-2,2':6',2-terpyridine In acetonitrile at 10℃; for 4h; Inert atmosphere; Glovebox; Sealed tube; Irradiation;
40% With tris(2,2-bipyridine)ruthenium(II) hexafluorophosphate; silver fluoride; 1-azido-1λ3-benzo[d][1,2]iodaoxol-3(1H)-one; 4,4',4-tri-tert-butyl-2,2':6',2-terpyridine In acetonitrile at 20℃; for 4h; Inert atmosphere; Sealed tube; Irradiation; 69 Example 6 1-(2-azido-1-(trifluoromethoxy)ethyl)-2,4,6-trimethylbenzene (4a) General procedure: Under the protection of N2, Ru(bpy)3(PF6)2 (2.4 mg, 0.00300 mmol, 1.0 mol%), AgF (19.2 mg, 0.150 mmol, 50.0 mol%) was added to the sealed tube. 4,4',4"-tri-tert-butyl-2,2':6',2"-terpyridine (tbtpy, 36.0 mg, 0.0900 mmol, 30.0 mol%),1-azido-1,3 benzo[d][1,2]iodohydroxy-3(1H)-one (3) (173.4 mg, 0.600 mmol, 2.00 eq.), then acetonitrile solvent (2.40 mL) ,4-phenylstyrene (1a) (43.9 mg, 0.300 mmol, 1.00 equiv), trifluoromethyl 4-methylbenzenesulfonate (2) (169 μL, 0.9 mmol, 3.00 equiv) was added to the reaction. The resulting mixture was then allowed to stand at room temperature and stirred under irradiation with a 14 W blue LED for 4 hours.After that, the reaction mixture was concentrated in vacuo and purified by silica gel chromatography.Elution with petroleum ether / ethyl acetate 100:1 (v / v) gave the corresponding product (4a), 65.5mg.
  • 28
  • [ 175676-42-3 ]
  • [ 3435-51-6 ]
  • 4-(2-azido-1-(trifluoromethoxy)ethyl)benzonitrile [ No CAS ]
YieldReaction ConditionsOperation in experiment
33% With tris(2,2-bipyridine)ruthenium(II) hexafluorophosphate; silver fluoride; 1-azido-1λ3-benzo[d][1,2]iodaoxol-3(1H)-one; 4,4',4-tri-tert-butyl-2,2':6',2-terpyridine In acetonitrile at 10℃; for 4h; Inert atmosphere; Glovebox; Sealed tube; Irradiation;
33% With tris(2,2-bipyridine)ruthenium(II) hexafluorophosphate; silver fluoride; 1-azido-1λ3-benzo[d][1,2]iodaoxol-3(1H)-one; 4,4',4-tri-tert-butyl-2,2':6',2-terpyridine In acetonitrile at 20℃; for 4h; Inert atmosphere; Sealed tube; Irradiation; 70 Example 6 1-(2-azido-1-(trifluoromethoxy)ethyl)-2,4,6-trimethylbenzene (4a) General procedure: Under the protection of N2, Ru(bpy)3(PF6)2 (2.4 mg, 0.00300 mmol, 1.0 mol%), AgF (19.2 mg, 0.150 mmol, 50.0 mol%) was added to the sealed tube. 4,4',4"-tri-tert-butyl-2,2':6',2"-terpyridine (tbtpy, 36.0 mg, 0.0900 mmol, 30.0 mol%),1-azido-1,3 benzo[d][1,2]iodohydroxy-3(1H)-one (3) (173.4 mg, 0.600 mmol, 2.00 eq.), then acetonitrile solvent (2.40 mL) ,4-phenylstyrene (1a) (43.9 mg, 0.300 mmol, 1.00 equiv), trifluoromethyl 4-methylbenzenesulfonate (2) (169 μL, 0.9 mmol, 3.00 equiv) was added to the reaction. The resulting mixture was then allowed to stand at room temperature and stirred under irradiation with a 14 W blue LED for 4 hours.After that, the reaction mixture was concentrated in vacuo and purified by silica gel chromatography.Elution with petroleum ether / ethyl acetate 100:1 (v / v) gave the corresponding product (4a), 65.5mg.
  • 29
  • [ 175676-42-3 ]
  • [ 1076-96-6 ]
  • methyl 4-(2-azido-1-(trifluoromethoxy)ethyl)benzoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
32% With tris(2,2-bipyridine)ruthenium(II) hexafluorophosphate; silver fluoride; 1-azido-1λ3-benzo[d][1,2]iodaoxol-3(1H)-one; 4,4',4-tri-tert-butyl-2,2':6',2-terpyridine In acetonitrile at 10℃; for 4h; Inert atmosphere; Glovebox; Sealed tube; Irradiation;
32% With tris(2,2-bipyridine)ruthenium(II) hexafluorophosphate; silver fluoride; 1-azido-1λ3-benzo[d][1,2]iodaoxol-3(1H)-one; 4,4',4-tri-tert-butyl-2,2':6',2-terpyridine In acetonitrile at 20℃; for 4h; Inert atmosphere; Sealed tube; Irradiation; 71 Example 6 1-(2-azido-1-(trifluoromethoxy)ethyl)-2,4,6-trimethylbenzene (4a) General procedure: Under the protection of N2, Ru(bpy)3(PF6)2 (2.4 mg, 0.00300 mmol, 1.0 mol%), AgF (19.2 mg, 0.150 mmol, 50.0 mol%) was added to the sealed tube. 4,4',4"-tri-tert-butyl-2,2':6',2"-terpyridine (tbtpy, 36.0 mg, 0.0900 mmol, 30.0 mol%),1-azido-1,3 benzo[d][1,2]iodohydroxy-3(1H)-one (3) (173.4 mg, 0.600 mmol, 2.00 eq.), then acetonitrile solvent (2.40 mL) ,4-phenylstyrene (1a) (43.9 mg, 0.300 mmol, 1.00 equiv), trifluoromethyl 4-methylbenzenesulfonate (2) (169 μL, 0.9 mmol, 3.00 equiv) was added to the reaction. The resulting mixture was then allowed to stand at room temperature and stirred under irradiation with a 14 W blue LED for 4 hours.After that, the reaction mixture was concentrated in vacuo and purified by silica gel chromatography.Elution with petroleum ether / ethyl acetate 100:1 (v / v) gave the corresponding product (4a), 65.5mg.
  • 30
  • [ 175676-42-3 ]
  • [ 827-54-3 ]
  • 2-(2-azido-1-(trifluoromethoxy)ethyl)naphthalene [ No CAS ]
YieldReaction ConditionsOperation in experiment
61% With tris(2,2-bipyridine)ruthenium(II) hexafluorophosphate; silver fluoride; 1-azido-1λ3-benzo[d][1,2]iodaoxol-3(1H)-one; 4,4',4-tri-tert-butyl-2,2':6',2-terpyridine In acetonitrile at 10℃; for 4h; Inert atmosphere; Glovebox; Sealed tube; Irradiation;
61% With tris(2,2-bipyridine)ruthenium(II) hexafluorophosphate; silver fluoride; 1-azido-1λ3-benzo[d][1,2]iodaoxol-3(1H)-one; 4,4',4-tri-tert-butyl-2,2':6',2-terpyridine In acetonitrile at 20℃; for 4h; Inert atmosphere; Sealed tube; Irradiation; 72 Example 6 1-(2-azido-1-(trifluoromethoxy)ethyl)-2,4,6-trimethylbenzene (4a) General procedure: Under the protection of N2, Ru(bpy)3(PF6)2 (2.4 mg, 0.00300 mmol, 1.0 mol%), AgF (19.2 mg, 0.150 mmol, 50.0 mol%) was added to the sealed tube. 4,4',4"-tri-tert-butyl-2,2':6',2"-terpyridine (tbtpy, 36.0 mg, 0.0900 mmol, 30.0 mol%),1-azido-1,3 benzo[d][1,2]iodohydroxy-3(1H)-one (3) (173.4 mg, 0.600 mmol, 2.00 eq.), then acetonitrile solvent (2.40 mL) ,4-phenylstyrene (1a) (43.9 mg, 0.300 mmol, 1.00 equiv), trifluoromethyl 4-methylbenzenesulfonate (2) (169 μL, 0.9 mmol, 3.00 equiv) was added to the reaction. The resulting mixture was then allowed to stand at room temperature and stirred under irradiation with a 14 W blue LED for 4 hours.After that, the reaction mixture was concentrated in vacuo and purified by silica gel chromatography.Elution with petroleum ether / ethyl acetate 100:1 (v / v) gave the corresponding product (4a), 65.5mg.
  • 31
  • [ 175676-42-3 ]
  • [ 826-74-4 ]
  • 1-(2-azido-1-(trifluoromethoxy)ethyl)naphthalene [ No CAS ]
YieldReaction ConditionsOperation in experiment
55% With tris(2,2-bipyridine)ruthenium(II) hexafluorophosphate; silver fluoride; 1-azido-1λ3-benzo[d][1,2]iodaoxol-3(1H)-one; 4,4',4-tri-tert-butyl-2,2':6',2-terpyridine In acetonitrile at 10℃; for 4h; Inert atmosphere; Glovebox; Sealed tube; Irradiation;
55% With tris(2,2-bipyridine)ruthenium(II) hexafluorophosphate; silver fluoride; 1-azido-1λ3-benzo[d][1,2]iodaoxol-3(1H)-one; 4,4',4-tri-tert-butyl-2,2':6',2-terpyridine In acetonitrile at 20℃; for 4h; Inert atmosphere; Sealed tube; Irradiation; 73 Example 6 1-(2-azido-1-(trifluoromethoxy)ethyl)-2,4,6-trimethylbenzene (4a) General procedure: Under the protection of N2, Ru(bpy)3(PF6)2 (2.4 mg, 0.00300 mmol, 1.0 mol%), AgF (19.2 mg, 0.150 mmol, 50.0 mol%) was added to the sealed tube. 4,4',4"-tri-tert-butyl-2,2':6',2"-terpyridine (tbtpy, 36.0 mg, 0.0900 mmol, 30.0 mol%),1-azido-1,3 benzo[d][1,2]iodohydroxy-3(1H)-one (3) (173.4 mg, 0.600 mmol, 2.00 eq.), then acetonitrile solvent (2.40 mL) ,4-phenylstyrene (1a) (43.9 mg, 0.300 mmol, 1.00 equiv), trifluoromethyl 4-methylbenzenesulfonate (2) (169 μL, 0.9 mmol, 3.00 equiv) was added to the reaction. The resulting mixture was then allowed to stand at room temperature and stirred under irradiation with a 14 W blue LED for 4 hours.After that, the reaction mixture was concentrated in vacuo and purified by silica gel chromatography.Elution with petroleum ether / ethyl acetate 100:1 (v / v) gave the corresponding product (4a), 65.5mg.
  • 32
  • [ 175676-42-3 ]
  • [ 78646-50-1 ]
  • 2-(2-azido-1-(trifluoromethoxy)ethyl)benzo[b]thiophene [ No CAS ]
YieldReaction ConditionsOperation in experiment
72% With tris(2,2-bipyridine)ruthenium(II) hexafluorophosphate; silver fluoride; 1-azido-1λ3-benzo[d][1,2]iodaoxol-3(1H)-one; 4,4',4-tri-tert-butyl-2,2':6',2-terpyridine In acetonitrile at 10℃; for 4h; Inert atmosphere; Glovebox; Sealed tube; Irradiation;
72% With tris(2,2-bipyridine)ruthenium(II) hexafluorophosphate; silver fluoride; 1-azido-1λ3-benzo[d][1,2]iodaoxol-3(1H)-one; 4,4',4-tri-tert-butyl-2,2':6',2-terpyridine In acetonitrile at 20℃; for 4h; Inert atmosphere; Sealed tube; Irradiation; 74 Example 6 1-(2-azido-1-(trifluoromethoxy)ethyl)-2,4,6-trimethylbenzene (4a) General procedure: Under the protection of N2, Ru(bpy)3(PF6)2 (2.4 mg, 0.00300 mmol, 1.0 mol%), AgF (19.2 mg, 0.150 mmol, 50.0 mol%) was added to the sealed tube. 4,4',4"-tri-tert-butyl-2,2':6',2"-terpyridine (tbtpy, 36.0 mg, 0.0900 mmol, 30.0 mol%),1-azido-1,3 benzo[d][1,2]iodohydroxy-3(1H)-one (3) (173.4 mg, 0.600 mmol, 2.00 eq.), then acetonitrile solvent (2.40 mL) ,4-phenylstyrene (1a) (43.9 mg, 0.300 mmol, 1.00 equiv), trifluoromethyl 4-methylbenzenesulfonate (2) (169 μL, 0.9 mmol, 3.00 equiv) was added to the reaction. The resulting mixture was then allowed to stand at room temperature and stirred under irradiation with a 14 W blue LED for 4 hours.After that, the reaction mixture was concentrated in vacuo and purified by silica gel chromatography.Elution with petroleum ether / ethyl acetate 100:1 (v / v) gave the corresponding product (4a), 65.5mg.
  • 33
  • [ 175676-42-3 ]
  • [ 5293-43-6 ]
  • 2-(2-azido-1-(trifluoromethoxy)ethyl)-1-bromo-4,5-dimethoxybenzene [ No CAS ]
YieldReaction ConditionsOperation in experiment
63% With tris(2,2-bipyridine)ruthenium(II) hexafluorophosphate; silver fluoride; 1-azido-1λ3-benzo[d][1,2]iodaoxol-3(1H)-one; 4,4',4-tri-tert-butyl-2,2':6',2-terpyridine In acetonitrile at 10℃; for 4h; Inert atmosphere; Glovebox; Sealed tube; Irradiation;
63% With tris(2,2-bipyridine)ruthenium(II) hexafluorophosphate; silver fluoride; 1-azido-1λ3-benzo[d][1,2]iodaoxol-3(1H)-one; 4,4',4-tri-tert-butyl-2,2':6',2-terpyridine In acetonitrile at 20℃; for 4h; Inert atmosphere; Sealed tube; Irradiation; 52 Example 6 1-(2-azido-1-(trifluoromethoxy)ethyl)-2,4,6-trimethylbenzene (4a) General procedure: Under the protection of N2, Ru(bpy)3(PF6)2 (2.4 mg, 0.00300 mmol, 1.0 mol%), AgF (19.2 mg, 0.150 mmol, 50.0 mol%) was added to the sealed tube. 4,4',4"-tri-tert-butyl-2,2':6',2"-terpyridine (tbtpy, 36.0 mg, 0.0900 mmol, 30.0 mol%),1-azido-1,3 benzo[d][1,2]iodohydroxy-3(1H)-one (3) (173.4 mg, 0.600 mmol, 2.00 eq.), then acetonitrile solvent (2.40 mL) ,4-phenylstyrene (1a) (43.9 mg, 0.300 mmol, 1.00 equiv), trifluoromethyl 4-methylbenzenesulfonate (2) (169 μL, 0.9 mmol, 3.00 equiv) was added to the reaction. The resulting mixture was then allowed to stand at room temperature and stirred under irradiation with a 14 W blue LED for 4 hours.After that, the reaction mixture was concentrated in vacuo and purified by silica gel chromatography.Elution with petroleum ether / ethyl acetate 100:1 (v / v) gave the corresponding product (4a), 65.5mg.
  • 34
  • [ 175676-42-3 ]
  • [ 1339650-73-5 ]
  • 1-(2-azido-1-(trifluoromethoxy)ethyl)-2-chloro-3,4-dimethoxybenzene [ No CAS ]
YieldReaction ConditionsOperation in experiment
65% With tris(2,2-bipyridine)ruthenium(II) hexafluorophosphate; silver fluoride; 1-azido-1λ3-benzo[d][1,2]iodaoxol-3(1H)-one; 4,4',4-tri-tert-butyl-2,2':6',2-terpyridine In acetonitrile at 10℃; for 4h; Inert atmosphere; Glovebox; Sealed tube; Irradiation;
65% With tris(2,2-bipyridine)ruthenium(II) hexafluorophosphate; silver fluoride; 1-azido-1λ3-benzo[d][1,2]iodaoxol-3(1H)-one; 4,4',4-tri-tert-butyl-2,2':6',2-terpyridine In acetonitrile at 20℃; for 4h; Inert atmosphere; Sealed tube; Irradiation; 53 Example 6 1-(2-azido-1-(trifluoromethoxy)ethyl)-2,4,6-trimethylbenzene (4a) General procedure: Under the protection of N2, Ru(bpy)3(PF6)2 (2.4 mg, 0.00300 mmol, 1.0 mol%), AgF (19.2 mg, 0.150 mmol, 50.0 mol%) was added to the sealed tube. 4,4',4"-tri-tert-butyl-2,2':6',2"-terpyridine (tbtpy, 36.0 mg, 0.0900 mmol, 30.0 mol%),1-azido-1,3 benzo[d][1,2]iodohydroxy-3(1H)-one (3) (173.4 mg, 0.600 mmol, 2.00 eq.), then acetonitrile solvent (2.40 mL) ,4-phenylstyrene (1a) (43.9 mg, 0.300 mmol, 1.00 equiv), trifluoromethyl 4-methylbenzenesulfonate (2) (169 μL, 0.9 mmol, 3.00 equiv) was added to the reaction. The resulting mixture was then allowed to stand at room temperature and stirred under irradiation with a 14 W blue LED for 4 hours.After that, the reaction mixture was concentrated in vacuo and purified by silica gel chromatography.Elution with petroleum ether / ethyl acetate 100:1 (v / v) gave the corresponding product (4a), 65.5mg.
  • 35
  • [ 175676-42-3 ]
  • [ 14568-68-4 ]
  • 2-(2-azido-1-(trifluoromethoxy)ethyl)-1,4-dimethoxybenzene [ No CAS ]
YieldReaction ConditionsOperation in experiment
35% With tris(2,2-bipyridine)ruthenium(II) hexafluorophosphate; silver fluoride; 1-azido-1λ3-benzo[d][1,2]iodaoxol-3(1H)-one; 4,4',4-tri-tert-butyl-2,2':6',2-terpyridine In acetonitrile at 10℃; for 4h; Inert atmosphere; Glovebox; Sealed tube; Irradiation;
35% With tris(2,2-bipyridine)ruthenium(II) hexafluorophosphate; silver fluoride; 1-azido-1λ3-benzo[d][1,2]iodaoxol-3(1H)-one; 4,4',4-tri-tert-butyl-2,2':6',2-terpyridine In acetonitrile at 20℃; for 4h; Inert atmosphere; Sealed tube; Irradiation; 54 Example 6 1-(2-azido-1-(trifluoromethoxy)ethyl)-2,4,6-trimethylbenzene (4a) General procedure: Under the protection of N2, Ru(bpy)3(PF6)2 (2.4 mg, 0.00300 mmol, 1.0 mol%), AgF (19.2 mg, 0.150 mmol, 50.0 mol%) was added to the sealed tube. 4,4',4"-tri-tert-butyl-2,2':6',2"-terpyridine (tbtpy, 36.0 mg, 0.0900 mmol, 30.0 mol%),1-azido-1,3 benzo[d][1,2]iodohydroxy-3(1H)-one (3) (173.4 mg, 0.600 mmol, 2.00 eq.), then acetonitrile solvent (2.40 mL) ,4-phenylstyrene (1a) (43.9 mg, 0.300 mmol, 1.00 equiv), trifluoromethyl 4-methylbenzenesulfonate (2) (169 μL, 0.9 mmol, 3.00 equiv) was added to the reaction. The resulting mixture was then allowed to stand at room temperature and stirred under irradiation with a 14 W blue LED for 4 hours.After that, the reaction mixture was concentrated in vacuo and purified by silica gel chromatography.Elution with petroleum ether / ethyl acetate 100:1 (v / v) gave the corresponding product (4a), 65.5mg.
  • 36
  • [ 175676-42-3 ]
  • [ 4973-29-9 ]
  • 1-(2-azido-1-(trifluoromethoxy)ethyl)-4-phenoxybenzene [ No CAS ]
YieldReaction ConditionsOperation in experiment
79% With tris(2,2-bipyridine)ruthenium(II) hexafluorophosphate; silver fluoride; 1-azido-1lambda3-benzo[d][1,2]iodaoxol-3(1H)-one; 4,4',4-tri-tert-butyl-2,2':6',2-terpyridine; In acetonitrile; at 20℃; for 4h;Inert atmosphere; Sealed tube; Irradiation; General procedure: Under the protection of N2, Ru(bpy)3(PF6)2 (2.4 mg, 0.00300 mmol, 1.0 mol%), AgF (19.2 mg, 0.150 mmol, 50.0 mol%) was added to the sealed tube. 4,4',4"-tri-tert-butyl-2,2':6',2"-terpyridine (tbtpy, 36.0 mg, 0.0900 mmol, 30.0 mol%),1-azido-1,3 benzo[d][1,2]iodohydroxy-3(1H)-one (3) (173.4 mg, 0.600 mmol, 2.00 eq.), then acetonitrile solvent (2.40 mL) ,4-phenylstyrene (1a) (43.9 mg, 0.300 mmol, 1.00 equiv), trifluoromethyl 4-methylbenzenesulfonate (2) (169 muL, 0.9 mmol, 3.00 equiv) was added to the reaction. The resulting mixture was then allowed to stand at room temperature and stirred under irradiation with a 14 W blue LED for 4 hours.After that, the reaction mixture was concentrated in vacuo and purified by silica gel chromatography.Elution with petroleum ether / ethyl acetate 100:1 (v / v) gave the corresponding product (4a), 65.5mg.
  • 37
  • [ 175676-42-3 ]
  • [ 2454-30-0 ]
  • 3-(2-azido-1-(trifluoromethoxy)ethyl)phenyl acetate [ No CAS ]
YieldReaction ConditionsOperation in experiment
38% With tris(2,2-bipyridine)ruthenium(II) hexafluorophosphate; silver fluoride; 1-azido-1λ3-benzo[d][1,2]iodaoxol-3(1H)-one; 4,4',4-tri-tert-butyl-2,2':6',2-terpyridine In acetonitrile at 10℃; for 4h; Inert atmosphere; Glovebox; Sealed tube; Irradiation;
38% With tris(2,2-bipyridine)ruthenium(II) hexafluorophosphate; silver fluoride; 1-azido-1λ3-benzo[d][1,2]iodaoxol-3(1H)-one; 4,4',4-tri-tert-butyl-2,2':6',2-terpyridine In acetonitrile at 20℃; for 4h; Inert atmosphere; Sealed tube; Irradiation; 59 Example 6 1-(2-azido-1-(trifluoromethoxy)ethyl)-2,4,6-trimethylbenzene (4a) General procedure: Under the protection of N2, Ru(bpy)3(PF6)2 (2.4 mg, 0.00300 mmol, 1.0 mol%), AgF (19.2 mg, 0.150 mmol, 50.0 mol%) was added to the sealed tube. 4,4',4"-tri-tert-butyl-2,2':6',2"-terpyridine (tbtpy, 36.0 mg, 0.0900 mmol, 30.0 mol%),1-azido-1,3 benzo[d][1,2]iodohydroxy-3(1H)-one (3) (173.4 mg, 0.600 mmol, 2.00 eq.), then acetonitrile solvent (2.40 mL) ,4-phenylstyrene (1a) (43.9 mg, 0.300 mmol, 1.00 equiv), trifluoromethyl 4-methylbenzenesulfonate (2) (169 μL, 0.9 mmol, 3.00 equiv) was added to the reaction. The resulting mixture was then allowed to stand at room temperature and stirred under irradiation with a 14 W blue LED for 4 hours.After that, the reaction mixture was concentrated in vacuo and purified by silica gel chromatography.Elution with petroleum ether / ethyl acetate 100:1 (v / v) gave the corresponding product (4a), 65.5mg.
  • 38
  • [ 175676-42-3 ]
  • 4-vinylphenyl 2-bromoacetate [ No CAS ]
  • 4-(2-azido-1-(trifluoromethoxy)ethyl)phenyl 2-bromoacetate [ No CAS ]
YieldReaction ConditionsOperation in experiment
55% With tris(2,2-bipyridine)ruthenium(II) hexafluorophosphate; silver fluoride; 1-azido-1λ3-benzo[d][1,2]iodaoxol-3(1H)-one; 4,4',4-tri-tert-butyl-2,2':6',2-terpyridine In acetonitrile at 10℃; for 4h; Inert atmosphere; Glovebox; Sealed tube; Irradiation;
55% With tris(2,2-bipyridine)ruthenium(II) hexafluorophosphate; silver fluoride; 1-azido-1λ3-benzo[d][1,2]iodaoxol-3(1H)-one; 4,4',4-tri-tert-butyl-2,2':6',2-terpyridine In acetonitrile at 20℃; for 4h; Inert atmosphere; Sealed tube; Irradiation; 60 Example 6 1-(2-azido-1-(trifluoromethoxy)ethyl)-2,4,6-trimethylbenzene (4a) General procedure: Under the protection of N2, Ru(bpy)3(PF6)2 (2.4 mg, 0.00300 mmol, 1.0 mol%), AgF (19.2 mg, 0.150 mmol, 50.0 mol%) was added to the sealed tube. 4,4',4"-tri-tert-butyl-2,2':6',2"-terpyridine (tbtpy, 36.0 mg, 0.0900 mmol, 30.0 mol%),1-azido-1,3 benzo[d][1,2]iodohydroxy-3(1H)-one (3) (173.4 mg, 0.600 mmol, 2.00 eq.), then acetonitrile solvent (2.40 mL) ,4-phenylstyrene (1a) (43.9 mg, 0.300 mmol, 1.00 equiv), trifluoromethyl 4-methylbenzenesulfonate (2) (169 μL, 0.9 mmol, 3.00 equiv) was added to the reaction. The resulting mixture was then allowed to stand at room temperature and stirred under irradiation with a 14 W blue LED for 4 hours.After that, the reaction mixture was concentrated in vacuo and purified by silica gel chromatography.Elution with petroleum ether / ethyl acetate 100:1 (v / v) gave the corresponding product (4a), 65.5mg.
  • 39
  • [ 175676-42-3 ]
  • [ 1240383-71-4 ]
  • 1-(2-azido-1-(trifluoromethoxy)ethyl)-4-(2-bromoethoxy)benzene [ No CAS ]
YieldReaction ConditionsOperation in experiment
73% With tris(2,2-bipyridine)ruthenium(II) hexafluorophosphate; silver fluoride; 1-azido-1λ3-benzo[d][1,2]iodaoxol-3(1H)-one; 4,4',4-tri-tert-butyl-2,2':6',2-terpyridine In acetonitrile at 10℃; for 4h; Inert atmosphere; Glovebox; Sealed tube; Irradiation;
73% With tris(2,2-bipyridine)ruthenium(II) hexafluorophosphate; silver fluoride; 1-azido-1λ3-benzo[d][1,2]iodaoxol-3(1H)-one; 4,4',4-tri-tert-butyl-2,2':6',2-terpyridine In acetonitrile at 20℃; for 4h; Inert atmosphere; Sealed tube; Irradiation; 61 Example 6 1-(2-azido-1-(trifluoromethoxy)ethyl)-2,4,6-trimethylbenzene (4a) General procedure: Under the protection of N2, Ru(bpy)3(PF6)2 (2.4 mg, 0.00300 mmol, 1.0 mol%), AgF (19.2 mg, 0.150 mmol, 50.0 mol%) was added to the sealed tube. 4,4',4"-tri-tert-butyl-2,2':6',2"-terpyridine (tbtpy, 36.0 mg, 0.0900 mmol, 30.0 mol%),1-azido-1,3 benzo[d][1,2]iodohydroxy-3(1H)-one (3) (173.4 mg, 0.600 mmol, 2.00 eq.), then acetonitrile solvent (2.40 mL) ,4-phenylstyrene (1a) (43.9 mg, 0.300 mmol, 1.00 equiv), trifluoromethyl 4-methylbenzenesulfonate (2) (169 μL, 0.9 mmol, 3.00 equiv) was added to the reaction. The resulting mixture was then allowed to stand at room temperature and stirred under irradiation with a 14 W blue LED for 4 hours.After that, the reaction mixture was concentrated in vacuo and purified by silica gel chromatography.Elution with petroleum ether / ethyl acetate 100:1 (v / v) gave the corresponding product (4a), 65.5mg.
  • 40
  • [ 175676-42-3 ]
  • [ 2350-89-2 ]
  • 1-(2-azido-1-(trifluoromethoxy)ethyl)-4-phenylbenzene [ No CAS ]
YieldReaction ConditionsOperation in experiment
67% With tris(2,2-bipyridine)ruthenium(II) hexafluorophosphate; silver fluoride; 1-azido-1λ3-benzo[d][1,2]iodaoxol-3(1H)-one; 4,4',4-tri-tert-butyl-2,2':6',2-terpyridine In acetonitrile at 10℃; for 4h; Inert atmosphere; Glovebox; Sealed tube; Irradiation;
65.5% With tris(2,2-bipyridine)ruthenium(II) hexafluorophosphate; silver fluoride; 1-azido-1λ3-benzo[d][1,2]iodaoxol-3(1H)-one; 4,4',4-tri-tert-butyl-2,2':6',2-terpyridine In acetonitrile at 20℃; for 4h; Inert atmosphere; Sealed tube; Irradiation; 6 Example 6 1-(2-azido-1-(trifluoromethoxy)ethyl)-2,4,6-trimethylbenzene (4a) Under the protection of N2, Ru(bpy)3(PF6)2 (2.4 mg, 0.00300 mmol, 1.0 mol%), AgF (19.2 mg, 0.150 mmol, 50.0 mol%) was added to the sealed tube. 4,4',4"-tri-tert-butyl-2,2':6',2"-terpyridine (tbtpy, 36.0 mg, 0.0900 mmol, 30.0 mol%),1-azido-1,3 benzo[d][1,2]iodohydroxy-3(1H)-one (3) (173.4 mg, 0.600 mmol, 2.00 eq.), then acetonitrile solvent (2.40 mL) ,4-phenylstyrene (1a) (43.9 mg, 0.300 mmol, 1.00 equiv), trifluoromethyl 4-methylbenzenesulfonate (2) (169 μL, 0.9 mmol, 3.00 equiv) was added to the reaction. The resulting mixture was then allowed to stand at room temperature and stirred under irradiation with a 14 W blue LED for 4 hours.After that, the reaction mixture was concentrated in vacuo and purified by silica gel chromatography.Elution with petroleum ether / ethyl acetate 100:1 (v / v) gave the corresponding product (4a), 65.5mg.
  • 41
  • [ 175676-42-3 ]
  • [ 769-25-5 ]
  • 1-(2-azido-1-(trifluoromethoxy)ethyl)-2,4,6-trimethylbenzene [ No CAS ]
YieldReaction ConditionsOperation in experiment
80% With tris(2,2-bipyridine)ruthenium(II) hexafluorophosphate; silver fluoride; 1-azido-1λ3-benzo[d][1,2]iodaoxol-3(1H)-one; 4,4',4-tri-tert-butyl-2,2':6',2-terpyridine In acetonitrile at 10℃; for 4h; Inert atmosphere; Glovebox; Sealed tube; Irradiation;
58% With tris(2,2-bipyridine)ruthenium(II) hexafluorophosphate; silver fluoride; 1-azido-1λ3-benzo[d][1,2]iodaoxol-3(1H)-one; 4,4',4-tri-tert-butyl-2,2':6',2-terpyridine In acetonitrile at 20℃; for 4h; Inert atmosphere; Sealed tube; Irradiation; 51 Example 6 1-(2-azido-1-(trifluoromethoxy)ethyl)-2,4,6-trimethylbenzene (4a) General procedure: Under the protection of N2, Ru(bpy)3(PF6)2 (2.4 mg, 0.00300 mmol, 1.0 mol%), AgF (19.2 mg, 0.150 mmol, 50.0 mol%) was added to the sealed tube. 4,4',4"-tri-tert-butyl-2,2':6',2"-terpyridine (tbtpy, 36.0 mg, 0.0900 mmol, 30.0 mol%),1-azido-1,3 benzo[d][1,2]iodohydroxy-3(1H)-one (3) (173.4 mg, 0.600 mmol, 2.00 eq.), then acetonitrile solvent (2.40 mL) ,4-phenylstyrene (1a) (43.9 mg, 0.300 mmol, 1.00 equiv), trifluoromethyl 4-methylbenzenesulfonate (2) (169 μL, 0.9 mmol, 3.00 equiv) was added to the reaction. The resulting mixture was then allowed to stand at room temperature and stirred under irradiation with a 14 W blue LED for 4 hours.After that, the reaction mixture was concentrated in vacuo and purified by silica gel chromatography.Elution with petroleum ether / ethyl acetate 100:1 (v / v) gave the corresponding product (4a), 65.5mg.
  • 42
  • [ 637-69-4 ]
  • [ 175676-42-3 ]
  • 1-(2-azido-1-(trifluoromethoxy)ethyl)-4-methoxybenzene [ No CAS ]
YieldReaction ConditionsOperation in experiment
60% With tris(2,2-bipyridine)ruthenium(II) hexafluorophosphate; silver fluoride; 1-azido-1λ3-benzo[d][1,2]iodaoxol-3(1H)-one; 4,4',4-tri-tert-butyl-2,2':6',2-terpyridine In acetonitrile at 10℃; for 4h; Inert atmosphere; Glovebox; Sealed tube; Irradiation;
60% With tris(2,2-bipyridine)ruthenium(II) hexafluorophosphate; silver fluoride; 1-azido-1λ3-benzo[d][1,2]iodaoxol-3(1H)-one; 4,4',4-tri-tert-butyl-2,2':6',2-terpyridine In acetonitrile at 20℃; for 4h; Inert atmosphere; Sealed tube; Irradiation; 55 Example 6 1-(2-azido-1-(trifluoromethoxy)ethyl)-2,4,6-trimethylbenzene (4a) General procedure: Under the protection of N2, Ru(bpy)3(PF6)2 (2.4 mg, 0.00300 mmol, 1.0 mol%), AgF (19.2 mg, 0.150 mmol, 50.0 mol%) was added to the sealed tube. 4,4',4"-tri-tert-butyl-2,2':6',2"-terpyridine (tbtpy, 36.0 mg, 0.0900 mmol, 30.0 mol%),1-azido-1,3 benzo[d][1,2]iodohydroxy-3(1H)-one (3) (173.4 mg, 0.600 mmol, 2.00 eq.), then acetonitrile solvent (2.40 mL) ,4-phenylstyrene (1a) (43.9 mg, 0.300 mmol, 1.00 equiv), trifluoromethyl 4-methylbenzenesulfonate (2) (169 μL, 0.9 mmol, 3.00 equiv) was added to the reaction. The resulting mixture was then allowed to stand at room temperature and stirred under irradiation with a 14 W blue LED for 4 hours.After that, the reaction mixture was concentrated in vacuo and purified by silica gel chromatography.Elution with petroleum ether / ethyl acetate 100:1 (v / v) gave the corresponding product (4a), 65.5mg.
  • 43
  • [ 175676-42-3 ]
  • [ 2628-16-2 ]
  • 4-(2-azido-1-(trifluoromethoxy)ethyl)phenyl acetate [ No CAS ]
YieldReaction ConditionsOperation in experiment
69% With tris(2,2-bipyridine)ruthenium(II) hexafluorophosphate; silver fluoride; 1-azido-1λ3-benzo[d][1,2]iodaoxol-3(1H)-one; 4,4',4-tri-tert-butyl-2,2':6',2-terpyridine In acetonitrile at 10℃; for 4h; Inert atmosphere; Glovebox; Sealed tube; Irradiation;
69% With tris(2,2-bipyridine)ruthenium(II) hexafluorophosphate; silver fluoride; 1-azido-1λ3-benzo[d][1,2]iodaoxol-3(1H)-one; 4,4',4-tri-tert-butyl-2,2':6',2-terpyridine In acetonitrile at 20℃; for 4h; Inert atmosphere; Sealed tube; Irradiation; 57 Example 6 1-(2-azido-1-(trifluoromethoxy)ethyl)-2,4,6-trimethylbenzene (4a) General procedure: Under the protection of N2, Ru(bpy)3(PF6)2 (2.4 mg, 0.00300 mmol, 1.0 mol%), AgF (19.2 mg, 0.150 mmol, 50.0 mol%) was added to the sealed tube. 4,4',4"-tri-tert-butyl-2,2':6',2"-terpyridine (tbtpy, 36.0 mg, 0.0900 mmol, 30.0 mol%),1-azido-1,3 benzo[d][1,2]iodohydroxy-3(1H)-one (3) (173.4 mg, 0.600 mmol, 2.00 eq.), then acetonitrile solvent (2.40 mL) ,4-phenylstyrene (1a) (43.9 mg, 0.300 mmol, 1.00 equiv), trifluoromethyl 4-methylbenzenesulfonate (2) (169 μL, 0.9 mmol, 3.00 equiv) was added to the reaction. The resulting mixture was then allowed to stand at room temperature and stirred under irradiation with a 14 W blue LED for 4 hours.After that, the reaction mixture was concentrated in vacuo and purified by silica gel chromatography.Elution with petroleum ether / ethyl acetate 100:1 (v / v) gave the corresponding product (4a), 65.5mg.
  • 44
  • [ 175676-42-3 ]
  • 4-vinylphenyl methanesulfonate [ No CAS ]
  • 4-(2-azido-1-(trifluoromethoxy)ethyl)phenyl methanesulfonate [ No CAS ]
YieldReaction ConditionsOperation in experiment
56% With tris(2,2-bipyridine)ruthenium(II) hexafluorophosphate; silver fluoride; 1-azido-1λ3-benzo[d][1,2]iodaoxol-3(1H)-one; 4,4',4-tri-tert-butyl-2,2':6',2-terpyridine In acetonitrile at 10℃; for 4h; Inert atmosphere; Glovebox; Sealed tube; Irradiation;
56% With tris(2,2-bipyridine)ruthenium(II) hexafluorophosphate; silver fluoride; 1-azido-1λ3-benzo[d][1,2]iodaoxol-3(1H)-one; 4,4',4-tri-tert-butyl-2,2':6',2-terpyridine In acetonitrile at 20℃; for 4h; Inert atmosphere; Sealed tube; Irradiation; 62 Example 6 1-(2-azido-1-(trifluoromethoxy)ethyl)-2,4,6-trimethylbenzene (4a) General procedure: Under the protection of N2, Ru(bpy)3(PF6)2 (2.4 mg, 0.00300 mmol, 1.0 mol%), AgF (19.2 mg, 0.150 mmol, 50.0 mol%) was added to the sealed tube. 4,4',4"-tri-tert-butyl-2,2':6',2"-terpyridine (tbtpy, 36.0 mg, 0.0900 mmol, 30.0 mol%),1-azido-1,3 benzo[d][1,2]iodohydroxy-3(1H)-one (3) (173.4 mg, 0.600 mmol, 2.00 eq.), then acetonitrile solvent (2.40 mL) ,4-phenylstyrene (1a) (43.9 mg, 0.300 mmol, 1.00 equiv), trifluoromethyl 4-methylbenzenesulfonate (2) (169 μL, 0.9 mmol, 3.00 equiv) was added to the reaction. The resulting mixture was then allowed to stand at room temperature and stirred under irradiation with a 14 W blue LED for 4 hours.After that, the reaction mixture was concentrated in vacuo and purified by silica gel chromatography.Elution with petroleum ether / ethyl acetate 100:1 (v / v) gave the corresponding product (4a), 65.5mg.
  • 45
  • [ 175676-42-3 ]
  • [ 1746-23-2 ]
  • 1-(2-azido-1-(trifluoromethoxy)ethyl)-4-(tert-butyl)benzene [ No CAS ]
YieldReaction ConditionsOperation in experiment
59% With tris(2,2-bipyridine)ruthenium(II) hexafluorophosphate; silver fluoride; 1-azido-1λ3-benzo[d][1,2]iodaoxol-3(1H)-one; 4,4',4-tri-tert-butyl-2,2':6',2-terpyridine In acetonitrile at 10℃; for 4h; Inert atmosphere; Glovebox; Sealed tube; Irradiation;
59% With tris(2,2-bipyridine)ruthenium(II) hexafluorophosphate; silver fluoride; 1-azido-1λ3-benzo[d][1,2]iodaoxol-3(1H)-one; 4,4',4-tri-tert-butyl-2,2':6',2-terpyridine In acetonitrile at 20℃; for 4h; Inert atmosphere; Sealed tube; Irradiation; 63 Example 6 1-(2-azido-1-(trifluoromethoxy)ethyl)-2,4,6-trimethylbenzene (4a) General procedure: Under the protection of N2, Ru(bpy)3(PF6)2 (2.4 mg, 0.00300 mmol, 1.0 mol%), AgF (19.2 mg, 0.150 mmol, 50.0 mol%) was added to the sealed tube. 4,4',4"-tri-tert-butyl-2,2':6',2"-terpyridine (tbtpy, 36.0 mg, 0.0900 mmol, 30.0 mol%),1-azido-1,3 benzo[d][1,2]iodohydroxy-3(1H)-one (3) (173.4 mg, 0.600 mmol, 2.00 eq.), then acetonitrile solvent (2.40 mL) ,4-phenylstyrene (1a) (43.9 mg, 0.300 mmol, 1.00 equiv), trifluoromethyl 4-methylbenzenesulfonate (2) (169 μL, 0.9 mmol, 3.00 equiv) was added to the reaction. The resulting mixture was then allowed to stand at room temperature and stirred under irradiation with a 14 W blue LED for 4 hours.After that, the reaction mixture was concentrated in vacuo and purified by silica gel chromatography.Elution with petroleum ether / ethyl acetate 100:1 (v / v) gave the corresponding product (4a), 65.5mg.
  • 46
  • [ 175676-42-3 ]
  • [ 622-97-9 ]
  • 1-(2-azido-1-(trifluoromethoxy)ethyl)-4-methylbenzene [ No CAS ]
YieldReaction ConditionsOperation in experiment
45% With tris(2,2-bipyridine)ruthenium(II) hexafluorophosphate; silver fluoride; 1-azido-1λ3-benzo[d][1,2]iodaoxol-3(1H)-one; 4,4',4-tri-tert-butyl-2,2':6',2-terpyridine In acetonitrile at 10℃; for 4h; Inert atmosphere; Glovebox; Sealed tube; Irradiation;
45% With tris(2,2-bipyridine)ruthenium(II) hexafluorophosphate; silver fluoride; 1-azido-1λ3-benzo[d][1,2]iodaoxol-3(1H)-one; 4,4',4-tri-tert-butyl-2,2':6',2-terpyridine In acetonitrile at 20℃; for 4h; Inert atmosphere; Sealed tube; Irradiation; 64 Example 6 1-(2-azido-1-(trifluoromethoxy)ethyl)-2,4,6-trimethylbenzene (4a) General procedure: Under the protection of N2, Ru(bpy)3(PF6)2 (2.4 mg, 0.00300 mmol, 1.0 mol%), AgF (19.2 mg, 0.150 mmol, 50.0 mol%) was added to the sealed tube. 4,4',4"-tri-tert-butyl-2,2':6',2"-terpyridine (tbtpy, 36.0 mg, 0.0900 mmol, 30.0 mol%),1-azido-1,3 benzo[d][1,2]iodohydroxy-3(1H)-one (3) (173.4 mg, 0.600 mmol, 2.00 eq.), then acetonitrile solvent (2.40 mL) ,4-phenylstyrene (1a) (43.9 mg, 0.300 mmol, 1.00 equiv), trifluoromethyl 4-methylbenzenesulfonate (2) (169 μL, 0.9 mmol, 3.00 equiv) was added to the reaction. The resulting mixture was then allowed to stand at room temperature and stirred under irradiation with a 14 W blue LED for 4 hours.After that, the reaction mixture was concentrated in vacuo and purified by silica gel chromatography.Elution with petroleum ether / ethyl acetate 100:1 (v / v) gave the corresponding product (4a), 65.5mg.
  • 47
  • [ 100-42-5 ]
  • [ 175676-42-3 ]
  • (2-azido-1-(trifluoromethoxy)ethyl)benzene [ No CAS ]
YieldReaction ConditionsOperation in experiment
41% With tris(2,2-bipyridine)ruthenium(II) hexafluorophosphate; silver fluoride; 1-azido-1λ3-benzo[d][1,2]iodaoxol-3(1H)-one; 4,4',4-tri-tert-butyl-2,2':6',2-terpyridine In acetonitrile at 10℃; for 4h; Inert atmosphere; Glovebox; Sealed tube; Irradiation;
41% With tris(2,2-bipyridine)ruthenium(II) hexafluorophosphate; silver fluoride; 1-azido-1λ3-benzo[d][1,2]iodaoxol-3(1H)-one; 4,4',4-tri-tert-butyl-2,2':6',2-terpyridine In acetonitrile at 20℃; for 4h; Inert atmosphere; Sealed tube; Irradiation; 65 Example 6 1-(2-azido-1-(trifluoromethoxy)ethyl)-2,4,6-trimethylbenzene (4a) General procedure: Under the protection of N2, Ru(bpy)3(PF6)2 (2.4 mg, 0.00300 mmol, 1.0 mol%), AgF (19.2 mg, 0.150 mmol, 50.0 mol%) was added to the sealed tube. 4,4',4"-tri-tert-butyl-2,2':6',2"-terpyridine (tbtpy, 36.0 mg, 0.0900 mmol, 30.0 mol%),1-azido-1,3 benzo[d][1,2]iodohydroxy-3(1H)-one (3) (173.4 mg, 0.600 mmol, 2.00 eq.), then acetonitrile solvent (2.40 mL) ,4-phenylstyrene (1a) (43.9 mg, 0.300 mmol, 1.00 equiv), trifluoromethyl 4-methylbenzenesulfonate (2) (169 μL, 0.9 mmol, 3.00 equiv) was added to the reaction. The resulting mixture was then allowed to stand at room temperature and stirred under irradiation with a 14 W blue LED for 4 hours.After that, the reaction mixture was concentrated in vacuo and purified by silica gel chromatography.Elution with petroleum ether / ethyl acetate 100:1 (v / v) gave the corresponding product (4a), 65.5mg.
  • 48
  • [ 175676-42-3 ]
  • [ 405-99-2 ]
  • 1-(2-azido-1-(trifluoromethoxy)ethyl)-4-fluorobenzene [ No CAS ]
YieldReaction ConditionsOperation in experiment
51% With tris(2,2-bipyridine)ruthenium(II) hexafluorophosphate; silver fluoride; 1-azido-1λ3-benzo[d][1,2]iodaoxol-3(1H)-one; 4,4',4-tri-tert-butyl-2,2':6',2-terpyridine In acetonitrile at 10℃; for 4h; Inert atmosphere; Glovebox; Sealed tube; Irradiation;
51% With tris(2,2-bipyridine)ruthenium(II) hexafluorophosphate; silver fluoride; 1-azido-1λ3-benzo[d][1,2]iodaoxol-3(1H)-one; 4,4',4-tri-tert-butyl-2,2':6',2-terpyridine In acetonitrile at 20℃; for 4h; Inert atmosphere; Sealed tube; Irradiation; 66 Example 6 1-(2-azido-1-(trifluoromethoxy)ethyl)-2,4,6-trimethylbenzene (4a) General procedure: Under the protection of N2, Ru(bpy)3(PF6)2 (2.4 mg, 0.00300 mmol, 1.0 mol%), AgF (19.2 mg, 0.150 mmol, 50.0 mol%) was added to the sealed tube. 4,4',4"-tri-tert-butyl-2,2':6',2"-terpyridine (tbtpy, 36.0 mg, 0.0900 mmol, 30.0 mol%),1-azido-1,3 benzo[d][1,2]iodohydroxy-3(1H)-one (3) (173.4 mg, 0.600 mmol, 2.00 eq.), then acetonitrile solvent (2.40 mL) ,4-phenylstyrene (1a) (43.9 mg, 0.300 mmol, 1.00 equiv), trifluoromethyl 4-methylbenzenesulfonate (2) (169 μL, 0.9 mmol, 3.00 equiv) was added to the reaction. The resulting mixture was then allowed to stand at room temperature and stirred under irradiation with a 14 W blue LED for 4 hours.After that, the reaction mixture was concentrated in vacuo and purified by silica gel chromatography.Elution with petroleum ether / ethyl acetate 100:1 (v / v) gave the corresponding product (4a), 65.5mg.
  • 49
  • [ 1073-67-2 ]
  • [ 175676-42-3 ]
  • 1-(2-azido-1-(trifluoromethoxy)ethyl)-4-chlorobenzene [ No CAS ]
YieldReaction ConditionsOperation in experiment
44% With tris(2,2-bipyridine)ruthenium(II) hexafluorophosphate; silver fluoride; 1-azido-1λ3-benzo[d][1,2]iodaoxol-3(1H)-one; 4,4',4-tri-tert-butyl-2,2':6',2-terpyridine In acetonitrile at 10℃; for 4h; Inert atmosphere; Glovebox; Sealed tube; Irradiation;
44% With tris(2,2-bipyridine)ruthenium(II) hexafluorophosphate; silver fluoride; 1-azido-1λ3-benzo[d][1,2]iodaoxol-3(1H)-one; 4,4',4-tri-tert-butyl-2,2':6',2-terpyridine In acetonitrile at 20℃; for 4h; Inert atmosphere; Sealed tube; Irradiation; 67 Example 6 1-(2-azido-1-(trifluoromethoxy)ethyl)-2,4,6-trimethylbenzene (4a) General procedure: Under the protection of N2, Ru(bpy)3(PF6)2 (2.4 mg, 0.00300 mmol, 1.0 mol%), AgF (19.2 mg, 0.150 mmol, 50.0 mol%) was added to the sealed tube. 4,4',4"-tri-tert-butyl-2,2':6',2"-terpyridine (tbtpy, 36.0 mg, 0.0900 mmol, 30.0 mol%),1-azido-1,3 benzo[d][1,2]iodohydroxy-3(1H)-one (3) (173.4 mg, 0.600 mmol, 2.00 eq.), then acetonitrile solvent (2.40 mL) ,4-phenylstyrene (1a) (43.9 mg, 0.300 mmol, 1.00 equiv), trifluoromethyl 4-methylbenzenesulfonate (2) (169 μL, 0.9 mmol, 3.00 equiv) was added to the reaction. The resulting mixture was then allowed to stand at room temperature and stirred under irradiation with a 14 W blue LED for 4 hours.After that, the reaction mixture was concentrated in vacuo and purified by silica gel chromatography.Elution with petroleum ether / ethyl acetate 100:1 (v / v) gave the corresponding product (4a), 65.5mg.
  • 50
  • [ 175676-42-3 ]
  • 6-vinylquinoline [ No CAS ]
  • 6-(2-azido-1-(trifluoromethoxy)ethyl)quinoline [ No CAS ]
YieldReaction ConditionsOperation in experiment
39% With tris(2,2-bipyridine)ruthenium(II) hexafluorophosphate; silver fluoride; 1-azido-1λ3-benzo[d][1,2]iodaoxol-3(1H)-one; 4,4',4-tri-tert-butyl-2,2':6',2-terpyridine In acetonitrile at 10℃; for 4h; Inert atmosphere; Glovebox; Sealed tube; Irradiation;
39% With tris(2,2-bipyridine)ruthenium(II) hexafluorophosphate; silver fluoride; 1-azido-1λ3-benzo[d][1,2]iodaoxol-3(1H)-one; 4,4',4-tri-tert-butyl-2,2':6',2-terpyridine In acetonitrile at 20℃; for 4h; Inert atmosphere; Sealed tube; Irradiation; 75 Example 6 1-(2-azido-1-(trifluoromethoxy)ethyl)-2,4,6-trimethylbenzene (4a) General procedure: Under the protection of N2, Ru(bpy)3(PF6)2 (2.4 mg, 0.00300 mmol, 1.0 mol%), AgF (19.2 mg, 0.150 mmol, 50.0 mol%) was added to the sealed tube. 4,4',4"-tri-tert-butyl-2,2':6',2"-terpyridine (tbtpy, 36.0 mg, 0.0900 mmol, 30.0 mol%),1-azido-1,3 benzo[d][1,2]iodohydroxy-3(1H)-one (3) (173.4 mg, 0.600 mmol, 2.00 eq.), then acetonitrile solvent (2.40 mL) ,4-phenylstyrene (1a) (43.9 mg, 0.300 mmol, 1.00 equiv), trifluoromethyl 4-methylbenzenesulfonate (2) (169 μL, 0.9 mmol, 3.00 equiv) was added to the reaction. The resulting mixture was then allowed to stand at room temperature and stirred under irradiation with a 14 W blue LED for 4 hours.After that, the reaction mixture was concentrated in vacuo and purified by silica gel chromatography.Elution with petroleum ether / ethyl acetate 100:1 (v / v) gave the corresponding product (4a), 65.5mg.
  • 51
  • [ 175676-42-3 ]
  • [ 63600-35-1 ]
  • 2-(2-azido-1-(trifluoromethoxy)ethyl)phenyl acetate [ No CAS ]
YieldReaction ConditionsOperation in experiment
50% With tris(2,2-bipyridine)ruthenium(II) hexafluorophosphate; silver fluoride; 1-azido-1λ3-benzo[d][1,2]iodaoxol-3(1H)-one; 4,4',4-tri-tert-butyl-2,2':6',2-terpyridine In acetonitrile at 10℃; for 4h; Inert atmosphere; Glovebox; Sealed tube; Irradiation;
50% With tris(2,2-bipyridine)ruthenium(II) hexafluorophosphate; silver fluoride; 1-azido-1λ3-benzo[d][1,2]iodaoxol-3(1H)-one; 4,4',4-tri-tert-butyl-2,2':6',2-terpyridine In acetonitrile at 20℃; for 4h; Inert atmosphere; Sealed tube; Irradiation; 58 Example 6 1-(2-azido-1-(trifluoromethoxy)ethyl)-2,4,6-trimethylbenzene (4a) General procedure: Under the protection of N2, Ru(bpy)3(PF6)2 (2.4 mg, 0.00300 mmol, 1.0 mol%), AgF (19.2 mg, 0.150 mmol, 50.0 mol%) was added to the sealed tube. 4,4',4"-tri-tert-butyl-2,2':6',2"-terpyridine (tbtpy, 36.0 mg, 0.0900 mmol, 30.0 mol%),1-azido-1,3 benzo[d][1,2]iodohydroxy-3(1H)-one (3) (173.4 mg, 0.600 mmol, 2.00 eq.), then acetonitrile solvent (2.40 mL) ,4-phenylstyrene (1a) (43.9 mg, 0.300 mmol, 1.00 equiv), trifluoromethyl 4-methylbenzenesulfonate (2) (169 μL, 0.9 mmol, 3.00 equiv) was added to the reaction. The resulting mixture was then allowed to stand at room temperature and stirred under irradiation with a 14 W blue LED for 4 hours.After that, the reaction mixture was concentrated in vacuo and purified by silica gel chromatography.Elution with petroleum ether / ethyl acetate 100:1 (v / v) gave the corresponding product (4a), 65.5mg.
  • 52
  • phenyltrifluoromethyl iodine chloride [ No CAS ]
  • [ 104-15-4 ]
  • [ 175676-42-3 ]
YieldReaction ConditionsOperation in experiment
68% In dichloromethane at 35℃; for 4h; Schlenk technique; Inert atmosphere;
  • 53
  • [ 175676-42-3 ]
  • [ 95-13-6 ]
  • C10H8F3N3O [ No CAS ]
  • C10H8F3N3O [ No CAS ]
YieldReaction ConditionsOperation in experiment
With tris(2,2-bipyridine)ruthenium(II) hexafluorophosphate; silver fluoride; 1-azido-1λ3-benzo[d][1,2]iodaoxol-3(1H)-one; 4,4',4-tri-tert-butyl-2,2':6',2-terpyridine In acetonitrile at 20℃; for 4h; Inert atmosphere; Sealed tube; Irradiation; Overall yield = 40 %; Optical yield = 28.571 %de; 76 Example 6 1-(2-azido-1-(trifluoromethoxy)ethyl)-2,4,6-trimethylbenzene (4a) General procedure: Under the protection of N2, Ru(bpy)3(PF6)2 (2.4 mg, 0.00300 mmol, 1.0 mol%), AgF (19.2 mg, 0.150 mmol, 50.0 mol%) was added to the sealed tube. 4,4',4"-tri-tert-butyl-2,2':6',2"-terpyridine (tbtpy, 36.0 mg, 0.0900 mmol, 30.0 mol%),1-azido-1,3 benzo[d][1,2]iodohydroxy-3(1H)-one (3) (173.4 mg, 0.600 mmol, 2.00 eq.), then acetonitrile solvent (2.40 mL) ,4-phenylstyrene (1a) (43.9 mg, 0.300 mmol, 1.00 equiv), trifluoromethyl 4-methylbenzenesulfonate (2) (169 μL, 0.9 mmol, 3.00 equiv) was added to the reaction. The resulting mixture was then allowed to stand at room temperature and stirred under irradiation with a 14 W blue LED for 4 hours.After that, the reaction mixture was concentrated in vacuo and purified by silica gel chromatography.Elution with petroleum ether / ethyl acetate 100:1 (v / v) gave the corresponding product (4a), 65.5mg.
  • 54
  • [ 175676-42-3 ]
  • [ 1221441-41-3 ]
  • C18H23F3N4O5 [ No CAS ]
  • C18H23F3N4O5 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With tris(2,2-bipyridine)ruthenium(II) hexafluorophosphate; silver fluoride; 1-azido-1λ3-benzo[d][1,2]iodaoxol-3(1H)-one; 4,4',4-tri-tert-butyl-2,2':6',2-terpyridine In acetonitrile at 20℃; for 4h; Inert atmosphere; Sealed tube; Irradiation; Overall yield = 40 %; Optical yield = 77.778 %de; 77 Example 6 1-(2-azido-1-(trifluoromethoxy)ethyl)-2,4,6-trimethylbenzene (4a) General procedure: Under the protection of N2, Ru(bpy)3(PF6)2 (2.4 mg, 0.00300 mmol, 1.0 mol%), AgF (19.2 mg, 0.150 mmol, 50.0 mol%) was added to the sealed tube. 4,4',4"-tri-tert-butyl-2,2':6',2"-terpyridine (tbtpy, 36.0 mg, 0.0900 mmol, 30.0 mol%),1-azido-1,3 benzo[d][1,2]iodohydroxy-3(1H)-one (3) (173.4 mg, 0.600 mmol, 2.00 eq.), then acetonitrile solvent (2.40 mL) ,4-phenylstyrene (1a) (43.9 mg, 0.300 mmol, 1.00 equiv), trifluoromethyl 4-methylbenzenesulfonate (2) (169 μL, 0.9 mmol, 3.00 equiv) was added to the reaction. The resulting mixture was then allowed to stand at room temperature and stirred under irradiation with a 14 W blue LED for 4 hours.After that, the reaction mixture was concentrated in vacuo and purified by silica gel chromatography.Elution with petroleum ether / ethyl acetate 100:1 (v / v) gave the corresponding product (4a), 65.5mg.
  • 55
  • [ 175676-42-3 ]
  • [ 151171-58-3 ]
  • C21H24F3N3O2 [ No CAS ]
  • C21H24F3N3O2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With tris(2,2-bipyridine)ruthenium(II) hexafluorophosphate; silver fluoride; 1-azido-1λ3-benzo[d][1,2]iodaoxol-3(1H)-one; 4,4',4-tri-tert-butyl-2,2':6',2-terpyridine In acetonitrile at 20℃; for 4h; Inert atmosphere; Sealed tube; Irradiation; Overall yield = 36 %; Optical yield = 81.818 %de; 78 Example 6 1-(2-azido-1-(trifluoromethoxy)ethyl)-2,4,6-trimethylbenzene (4a) General procedure: Under the protection of N2, Ru(bpy)3(PF6)2 (2.4 mg, 0.00300 mmol, 1.0 mol%), AgF (19.2 mg, 0.150 mmol, 50.0 mol%) was added to the sealed tube. 4,4',4"-tri-tert-butyl-2,2':6',2"-terpyridine (tbtpy, 36.0 mg, 0.0900 mmol, 30.0 mol%),1-azido-1,3 benzo[d][1,2]iodohydroxy-3(1H)-one (3) (173.4 mg, 0.600 mmol, 2.00 eq.), then acetonitrile solvent (2.40 mL) ,4-phenylstyrene (1a) (43.9 mg, 0.300 mmol, 1.00 equiv), trifluoromethyl 4-methylbenzenesulfonate (2) (169 μL, 0.9 mmol, 3.00 equiv) was added to the reaction. The resulting mixture was then allowed to stand at room temperature and stirred under irradiation with a 14 W blue LED for 4 hours.After that, the reaction mixture was concentrated in vacuo and purified by silica gel chromatography.Elution with petroleum ether / ethyl acetate 100:1 (v / v) gave the corresponding product (4a), 65.5mg.
  • 56
  • [ 175676-42-3 ]
  • C40H56O4 [ No CAS ]
  • C41H56F3N3O5 [ No CAS ]
  • C41H56F3N3O5 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With tris(2,2-bipyridine)ruthenium(II) hexafluorophosphate; silver fluoride; 1-azido-1λ3-benzo[d][1,2]iodaoxol-3(1H)-one; 4,4',4-tri-tert-butyl-2,2':6',2-terpyridine In acetonitrile at 20℃; for 4h; Inert atmosphere; Sealed tube; Irradiation; Overall yield = 38 %; Optical yield = 60 %de; 79 Example 6 1-(2-azido-1-(trifluoromethoxy)ethyl)-2,4,6-trimethylbenzene (4a) General procedure: Under the protection of N2, Ru(bpy)3(PF6)2 (2.4 mg, 0.00300 mmol, 1.0 mol%), AgF (19.2 mg, 0.150 mmol, 50.0 mol%) was added to the sealed tube. 4,4',4"-tri-tert-butyl-2,2':6',2"-terpyridine (tbtpy, 36.0 mg, 0.0900 mmol, 30.0 mol%),1-azido-1,3 benzo[d][1,2]iodohydroxy-3(1H)-one (3) (173.4 mg, 0.600 mmol, 2.00 eq.), then acetonitrile solvent (2.40 mL) ,4-phenylstyrene (1a) (43.9 mg, 0.300 mmol, 1.00 equiv), trifluoromethyl 4-methylbenzenesulfonate (2) (169 μL, 0.9 mmol, 3.00 equiv) was added to the reaction. The resulting mixture was then allowed to stand at room temperature and stirred under irradiation with a 14 W blue LED for 4 hours.After that, the reaction mixture was concentrated in vacuo and purified by silica gel chromatography.Elution with petroleum ether / ethyl acetate 100:1 (v / v) gave the corresponding product (4a), 65.5mg.
  • 57
  • [ 175676-42-3 ]
  • gibberellate 4-vinylphenyl ester diacetate [ No CAS ]
  • C32H32F3N3O9 [ No CAS ]
  • C32H32F3N3O9 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With tris(2,2-bipyridine)ruthenium(II) hexafluorophosphate; silver fluoride; 1-azido-1λ3-benzo[d][1,2]iodaoxol-3(1H)-one; 4,4',4-tri-tert-butyl-2,2':6',2-terpyridine In acetonitrile at 20℃; for 4h; Inert atmosphere; Sealed tube; Irradiation; Overall yield = 28 %; Optical yield = 20 %de; 80 Example 6 1-(2-azido-1-(trifluoromethoxy)ethyl)-2,4,6-trimethylbenzene (4a) General procedure: Under the protection of N2, Ru(bpy)3(PF6)2 (2.4 mg, 0.00300 mmol, 1.0 mol%), AgF (19.2 mg, 0.150 mmol, 50.0 mol%) was added to the sealed tube. 4,4',4"-tri-tert-butyl-2,2':6',2"-terpyridine (tbtpy, 36.0 mg, 0.0900 mmol, 30.0 mol%),1-azido-1,3 benzo[d][1,2]iodohydroxy-3(1H)-one (3) (173.4 mg, 0.600 mmol, 2.00 eq.), then acetonitrile solvent (2.40 mL) ,4-phenylstyrene (1a) (43.9 mg, 0.300 mmol, 1.00 equiv), trifluoromethyl 4-methylbenzenesulfonate (2) (169 μL, 0.9 mmol, 3.00 equiv) was added to the reaction. The resulting mixture was then allowed to stand at room temperature and stirred under irradiation with a 14 W blue LED for 4 hours.After that, the reaction mixture was concentrated in vacuo and purified by silica gel chromatography.Elution with petroleum ether / ethyl acetate 100:1 (v / v) gave the corresponding product (4a), 65.5mg.
  • 58
  • [ 175676-42-3 ]
  • 10β-(4’-vinylphenyl)dihydroartemisinin [ No CAS ]
  • C25H32F3N3O6 [ No CAS ]
  • C25H32F3N3O6 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With tris(2,2-bipyridine)ruthenium(II) hexafluorophosphate; silver fluoride; 1-azido-1λ3-benzo[d][1,2]iodaoxol-3(1H)-one; 4,4',4-tri-tert-butyl-2,2':6',2-terpyridine In acetonitrile at 20℃; for 4h; Inert atmosphere; Sealed tube; Irradiation; Overall yield = 28 %; Optical yield = 33.333 %de; 81 Example 6 1-(2-azido-1-(trifluoromethoxy)ethyl)-2,4,6-trimethylbenzene (4a) General procedure: Under the protection of N2, Ru(bpy)3(PF6)2 (2.4 mg, 0.00300 mmol, 1.0 mol%), AgF (19.2 mg, 0.150 mmol, 50.0 mol%) was added to the sealed tube. 4,4',4"-tri-tert-butyl-2,2':6',2"-terpyridine (tbtpy, 36.0 mg, 0.0900 mmol, 30.0 mol%),1-azido-1,3 benzo[d][1,2]iodohydroxy-3(1H)-one (3) (173.4 mg, 0.600 mmol, 2.00 eq.), then acetonitrile solvent (2.40 mL) ,4-phenylstyrene (1a) (43.9 mg, 0.300 mmol, 1.00 equiv), trifluoromethyl 4-methylbenzenesulfonate (2) (169 μL, 0.9 mmol, 3.00 equiv) was added to the reaction. The resulting mixture was then allowed to stand at room temperature and stirred under irradiation with a 14 W blue LED for 4 hours.After that, the reaction mixture was concentrated in vacuo and purified by silica gel chromatography.Elution with petroleum ether / ethyl acetate 100:1 (v / v) gave the corresponding product (4a), 65.5mg.
  • 59
  • [ 175676-42-3 ]
  • C20H33N3O5Si [ No CAS ]
  • C15H18F3N3O3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
59% With 3,4,7,8-Tetramethyl-o-phenanthrolin; silver fluoride; Selectfluor In dichloromethane; acetonitrile at 25℃; Inert atmosphere;
  • 60
  • [ 175676-42-3 ]
  • C22H38O5Si [ No CAS ]
  • 5-(trifluoromethoxy)pentyl 4-(tert-butyl)benzoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
66% With 3,4,7,8-Tetramethyl-o-phenanthrolin; silver fluoride; Selectfluor In dichloromethane; acetonitrile at 25℃; Inert atmosphere;
  • 61
  • [ 175676-42-3 ]
  • C19H32O6Si [ No CAS ]
  • C14H17F3O4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
66% With 3,4,7,8-Tetramethyl-o-phenanthrolin; silver fluoride; Selectfluor In dichloromethane; acetonitrile at 25℃; Inert atmosphere;
  • 62
  • [ 175676-42-3 ]
  • C18H29FO5Si [ No CAS ]
  • 5-trifluoromethoxy-1-pentanol 4-fluorobenzoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
59% With 3,4,7,8-Tetramethyl-o-phenanthrolin; silver fluoride; Selectfluor In dichloromethane; acetonitrile at 25℃; Inert atmosphere;
  • 63
  • [ 175676-42-3 ]
  • C18H29ClO5Si [ No CAS ]
  • C13H14ClF3O3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
61% With 3,4,7,8-Tetramethyl-o-phenanthrolin; silver fluoride; Selectfluor In dichloromethane; acetonitrile at 25℃; Inert atmosphere;
  • 64
  • [ 175676-42-3 ]
  • C20H33BrO5Si [ No CAS ]
  • C15H18BrF3O3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
59% With 3,4,7,8-Tetramethyl-o-phenanthrolin; silver fluoride; Selectfluor In dichloromethane; acetonitrile at 25℃; Inert atmosphere;
  • 65
  • [ 175676-42-3 ]
  • C19H29F3O5Si [ No CAS ]
  • 5-(trifluoromethoxy)pentyl 4-(trifluoromethyl)benzoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
56% With 3,4,7,8-Tetramethyl-o-phenanthrolin; silver fluoride; Selectfluor In dichloromethane; acetonitrile at 25℃; Inert atmosphere;
  • 66
  • [ 175676-42-3 ]
  • C22H32O5Si [ No CAS ]
  • C17H17F3O3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
61% With 3,4,7,8-Tetramethyl-o-phenanthrolin; silver fluoride; Selectfluor In dichloromethane; acetonitrile at 25℃; Inert atmosphere;
  • 67
  • [ 175676-42-3 ]
  • C17H28FNO5Si [ No CAS ]
  • C12H13F4NO3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
61% With 3,4,7,8-Tetramethyl-o-phenanthrolin; silver fluoride; Selectfluor In dichloromethane; acetonitrile at 25℃; Inert atmosphere;
  • 68
  • [ 175676-42-3 ]
  • [ 18536-91-9 ]
  • dodecyl trifluoromethyl ether [ No CAS ]
YieldReaction ConditionsOperation in experiment
57% With 3,4,7,8-Tetramethyl-o-phenanthrolin; silver fluoride; Selectfluor In dichloromethane; acetonitrile at 25℃; Inert atmosphere;
  • 69
  • [ 175676-42-3 ]
  • C16H27BrO5SSi [ No CAS ]
  • C11H12BrF3O3S [ No CAS ]
YieldReaction ConditionsOperation in experiment
62% With 3,4,7,8-Tetramethyl-o-phenanthrolin; silver fluoride; Selectfluor In dichloromethane; acetonitrile at 25℃; Inert atmosphere;
  • 70
  • [ 175676-42-3 ]
  • C20H30O6Si [ No CAS ]
  • C15H15F3O4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
56% With 3,4,7,8-Tetramethyl-o-phenanthrolin; silver fluoride; Selectfluor In dichloromethane; acetonitrile at 25℃; Inert atmosphere;
  • 71
  • [ 175676-42-3 ]
  • C20H31NO5Si [ No CAS ]
  • C15H16F3NO3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
65% With 3,4,7,8-Tetramethyl-o-phenanthrolin; silver fluoride; Selectfluor In dichloromethane; acetonitrile at 25℃; Inert atmosphere;
  • 72
  • [ 175676-42-3 ]
  • [ 252054-88-9 ]
  • 2-iodo-1-(trifluoromethoxy)naphthalene [ No CAS ]
  • 1-iodo-2-(trifluoromethoxy)naphthalene [ No CAS ]
YieldReaction ConditionsOperation in experiment
With potassium fluoride; 1-iodo-2,2,3,3,4,4,5,5,5-nonafluorobutane; cis-dicyclohexano-18-C-6; carbonic acid dimethyl ester at 60℃; for 12h; Overall yield = 86 %; 3. General Procedure for Trifluoromethoxylation-iodination of Arynes 3a-3m General procedure: To a 15 mL of pressure-proof pipe equipped with a stir bar was added 1 (0.50 mmol, 1.00 equiv), cis-DCy-18-C-6 (372.49 mg, 1.00 mmol, 2.0 equiv), C4F9I (1037.79 mg, 3.00 mmol, 6.00 equiv) and DMC (3.0 mL) in the glove box. 2a (240.20 mg, 1.00 mmol, 2.0 equiv) and KF (116.20 mg, 2.00 mmol, 4.00 equiv) were added with stirring at room temperature. The reaction was stirred at 60 °C for 12 h and cooled to room temperature. The solvent was evaporated under vacuum and the crude product was purified by flash column chromatography to give products 3. Yields were listed in Table 5. The ratio of regioisomer ab/ba was determined by 19F NMR spectroscopy.
  • 73
  • [ 175676-42-3 ]
  • [ 262373-15-9 ]
  • 2-iodo-5-methyl-1-(trifluoromethoxy)benzene [ No CAS ]
  • 2-iodo-4-methyl-1-(trifluoromethoxy)benzene [ No CAS ]
YieldReaction ConditionsOperation in experiment
With potassium fluoride; 1-iodo-2,2,3,3,4,4,5,5,5-nonafluorobutane; cis-dicyclohexano-18-C-6; carbonic acid dimethyl ester; at 60℃; for 12h; General procedure: To a 15 mL of pressure-proof pipe equipped with a stir bar was added 1 (0.50 mmol, 1.00 equiv), cis-DCy-18-C-6 (372.49 mg, 1.00 mmol, 2.0 equiv), C4F9I (1037.79 mg, 3.00 mmol, 6.00 equiv) and DMC (3.0 mL) in the glove box. 2a (240.20 mg, 1.00 mmol, 2.0 equiv) and KF (116.20 mg, 2.00 mmol, 4.00 equiv) were added with stirring at room temperature. The reaction was stirred at 60 C for 12 h and cooled to room temperature. The solvent was evaporated under vacuum and the crude product was purified by flash column chromatography to give products 3. Yields were listed in Table 5. The ratio of regioisomer ab/ba was determined by 19F NMR spectroscopy.
  • 74
  • [ 175676-42-3 ]
  • C12H17F3O3SSi [ No CAS ]
  • 2-iodo-5-ethyl-1-(trifluoromethoxy)benzene [ No CAS ]
  • 2-iodo-4-ethyl-1-(trifluoromethoxy)benzene [ No CAS ]
YieldReaction ConditionsOperation in experiment
With potassium fluoride; 1-iodo-2,2,3,3,4,4,5,5,5-nonafluorobutane; cis-dicyclohexano-18-C-6; carbonic acid dimethyl ester at 60℃; for 12h; Overall yield = 57 %; 3. General Procedure for Trifluoromethoxylation-iodination of Arynes 3a-3m General procedure: To a 15 mL of pressure-proof pipe equipped with a stir bar was added 1 (0.50 mmol, 1.00 equiv), cis-DCy-18-C-6 (372.49 mg, 1.00 mmol, 2.0 equiv), C4F9I (1037.79 mg, 3.00 mmol, 6.00 equiv) and DMC (3.0 mL) in the glove box. 2a (240.20 mg, 1.00 mmol, 2.0 equiv) and KF (116.20 mg, 2.00 mmol, 4.00 equiv) were added with stirring at room temperature. The reaction was stirred at 60 °C for 12 h and cooled to room temperature. The solvent was evaporated under vacuum and the crude product was purified by flash column chromatography to give products 3. Yields were listed in Table 5. The ratio of regioisomer ab/ba was determined by 19F NMR spectroscopy.
  • 75
  • [ 175676-42-3 ]
  • C13H19F3O3SSi [ No CAS ]
  • 2-iodo-5-isopropyl-1-(trifluoromethoxy)benzene [ No CAS ]
  • 2-iodo-4-isopropyl-1-(trifluoromethoxy)benzene [ No CAS ]
YieldReaction ConditionsOperation in experiment
With potassium fluoride; 1-iodo-2,2,3,3,4,4,5,5,5-nonafluorobutane; cis-dicyclohexano-18-C-6; carbonic acid dimethyl ester at 60℃; for 12h; Overall yield = 53 %; 3. General Procedure for Trifluoromethoxylation-iodination of Arynes 3a-3m General procedure: To a 15 mL of pressure-proof pipe equipped with a stir bar was added 1 (0.50 mmol, 1.00 equiv), cis-DCy-18-C-6 (372.49 mg, 1.00 mmol, 2.0 equiv), C4F9I (1037.79 mg, 3.00 mmol, 6.00 equiv) and DMC (3.0 mL) in the glove box. 2a (240.20 mg, 1.00 mmol, 2.0 equiv) and KF (116.20 mg, 2.00 mmol, 4.00 equiv) were added with stirring at room temperature. The reaction was stirred at 60 °C for 12 h and cooled to room temperature. The solvent was evaporated under vacuum and the crude product was purified by flash column chromatography to give products 3. Yields were listed in Table 5. The ratio of regioisomer ab/ba was determined by 19F NMR spectroscopy.
  • 76
  • [ 175676-42-3 ]
  • [ 1315568-69-4 ]
  • 2-iodo-5-tert-butyl-1-(trifluoromethoxy)benzene [ No CAS ]
  • 2-iodo-4-tert-butyl-1-(trifluoromethoxy)benzene [ No CAS ]
YieldReaction ConditionsOperation in experiment
With potassium fluoride; 1-iodo-2,2,3,3,4,4,5,5,5-nonafluorobutane; cis-dicyclohexano-18-C-6; carbonic acid dimethyl ester at 60℃; for 12h; Overall yield = 53 %; 3. General Procedure for Trifluoromethoxylation-iodination of Arynes 3a-3m General procedure: To a 15 mL of pressure-proof pipe equipped with a stir bar was added 1 (0.50 mmol, 1.00 equiv), cis-DCy-18-C-6 (372.49 mg, 1.00 mmol, 2.0 equiv), C4F9I (1037.79 mg, 3.00 mmol, 6.00 equiv) and DMC (3.0 mL) in the glove box. 2a (240.20 mg, 1.00 mmol, 2.0 equiv) and KF (116.20 mg, 2.00 mmol, 4.00 equiv) were added with stirring at room temperature. The reaction was stirred at 60 °C for 12 h and cooled to room temperature. The solvent was evaporated under vacuum and the crude product was purified by flash column chromatography to give products 3. Yields were listed in Table 5. The ratio of regioisomer ab/ba was determined by 19F NMR spectroscopy.
  • 77
  • [ 175676-42-3 ]
  • 4-fluoro-2-(trimethylsilyl)phenyl trifluoromethanesulfonate [ No CAS ]
  • 4-fluoro-2-iodo-1-(trifluoromethoxy)benzene [ No CAS ]
  • 4-fluoro-1-iodo-2-(trifluoromethoxy)benzene [ No CAS ]
YieldReaction ConditionsOperation in experiment
With potassium fluoride; 1-iodo-2,2,3,3,4,4,5,5,5-nonafluorobutane; cis-dicyclohexano-18-C-6; carbonic acid dimethyl ester at 60℃; for 12h; Overall yield = 66 %Spectr.; 3. General Procedure for Trifluoromethoxylation-iodination of Arynes 3a-3m General procedure: To a 15 mL of pressure-proof pipe equipped with a stir bar was added 1 (0.50 mmol, 1.00 equiv), cis-DCy-18-C-6 (372.49 mg, 1.00 mmol, 2.0 equiv), C4F9I (1037.79 mg, 3.00 mmol, 6.00 equiv) and DMC (3.0 mL) in the glove box. 2a (240.20 mg, 1.00 mmol, 2.0 equiv) and KF (116.20 mg, 2.00 mmol, 4.00 equiv) were added with stirring at room temperature. The reaction was stirred at 60 °C for 12 h and cooled to room temperature. The solvent was evaporated under vacuum and the crude product was purified by flash column chromatography to give products 3. Yields were listed in Table 5. The ratio of regioisomer ab/ba was determined by 19F NMR spectroscopy.
  • 78
  • [ 175676-42-3 ]
  • 4-methoxy-2-(trimethylsilyl)phenyl triflate [ No CAS ]
  • 2-iodo-4-methoxy-1-(trifluoromethoxy)benzene [ No CAS ]
  • 2-iodo-5-methoxy-1-(trifluoromethoxy)benzene [ No CAS ]
YieldReaction ConditionsOperation in experiment
With potassium fluoride; 1-iodo-2,2,3,3,4,4,5,5,5-nonafluorobutane; cis-dicyclohexano-18-C-6; carbonic acid dimethyl ester at 60℃; for 12h; Overall yield = 64 %; 3. General Procedure for Trifluoromethoxylation-iodination of Arynes 3a-3m General procedure: To a 15 mL of pressure-proof pipe equipped with a stir bar was added 1 (0.50 mmol, 1.00 equiv), cis-DCy-18-C-6 (372.49 mg, 1.00 mmol, 2.0 equiv), C4F9I (1037.79 mg, 3.00 mmol, 6.00 equiv) and DMC (3.0 mL) in the glove box. 2a (240.20 mg, 1.00 mmol, 2.0 equiv) and KF (116.20 mg, 2.00 mmol, 4.00 equiv) were added with stirring at room temperature. The reaction was stirred at 60 °C for 12 h and cooled to room temperature. The solvent was evaporated under vacuum and the crude product was purified by flash column chromatography to give products 3. Yields were listed in Table 5. The ratio of regioisomer ab/ba was determined by 19F NMR spectroscopy.
  • 79
  • [ 175676-42-3 ]
  • 3-(trimethylsilyl)-[1,1’-biphenyl]-4-yl trifluoromethanesulfonate [ No CAS ]
  • 2-iodo-5-phenyl-1-(trifluoromethoxy)benzene [ No CAS ]
  • 2-iodo-4-phenyl-1-(trifluoromethoxy)benzene [ No CAS ]
YieldReaction ConditionsOperation in experiment
With potassium fluoride; 1-iodo-2,2,3,3,4,4,5,5,5-nonafluorobutane; cis-dicyclohexano-18-C-6; carbonic acid dimethyl ester at 60℃; for 12h; Overall yield = 68 %; 3. General Procedure for Trifluoromethoxylation-iodination of Arynes 3a-3m General procedure: To a 15 mL of pressure-proof pipe equipped with a stir bar was added 1 (0.50 mmol, 1.00 equiv), cis-DCy-18-C-6 (372.49 mg, 1.00 mmol, 2.0 equiv), C4F9I (1037.79 mg, 3.00 mmol, 6.00 equiv) and DMC (3.0 mL) in the glove box. 2a (240.20 mg, 1.00 mmol, 2.0 equiv) and KF (116.20 mg, 2.00 mmol, 4.00 equiv) were added with stirring at room temperature. The reaction was stirred at 60 °C for 12 h and cooled to room temperature. The solvent was evaporated under vacuum and the crude product was purified by flash column chromatography to give products 3. Yields were listed in Table 5. The ratio of regioisomer ab/ba was determined by 19F NMR spectroscopy.
  • 80
  • [ 175676-42-3 ]
  • [ 88284-48-4 ]
  • [ 175278-00-9 ]
YieldReaction ConditionsOperation in experiment
64% With potassium fluoride; 1-iodo-2,2,3,3,4,4,5,5,5-nonafluorobutane; cis-dicyclohexano-18-C-6; carbonic acid dimethyl ester; at 60℃; for 12h; General procedure: To a 15 mL of pressure-proof pipe equipped with a stir bar was added 1 (0.50 mmol, 1.00 equiv), cis-DCy-18-C-6 (372.49 mg, 1.00 mmol, 2.0 equiv), C4F9I (1037.79 mg, 3.00 mmol, 6.00 equiv) and DMC (3.0 mL) in the glove box. 2a (240.20 mg, 1.00 mmol, 2.0 equiv) and KF (116.20 mg, 2.00 mmol, 4.00 equiv) were added with stirring at room temperature. The reaction was stirred at 60 C for 12 h and cooled to room temperature. The solvent was evaporated under vacuum and the crude product was purified by flash column chromatography to give products 3. Yields were listed in Table 5. The ratio of regioisomer ab/ba was determined by 19F NMR spectroscopy.
  • 81
  • [ 175676-42-3 ]
  • [ 88284-48-4 ]
  • [ 456-55-3 ]
  • [ 175278-00-9 ]
  • 82
  • [ 175676-42-3 ]
  • 2,4-dimethyl-6-(trimethylsilyl)phenyl trifluoromethanesulfonate [ No CAS ]
  • 2-iodo-4,6-dimethyl-1-(trifluoromethoxy)benzene [ No CAS ]
  • 2-iodo-3,5-dimethyl-1-(trifluoromethoxy)benzene [ No CAS ]
YieldReaction ConditionsOperation in experiment
With potassium fluoride; 1-iodo-2,2,3,3,4,4,5,5,5-nonafluorobutane; cis-dicyclohexano-18-C-6; carbonic acid dimethyl ester at 60℃; for 12h; Overall yield = 60 %; 3. General Procedure for Trifluoromethoxylation-iodination of Arynes 3a-3m General procedure: To a 15 mL of pressure-proof pipe equipped with a stir bar was added 1 (0.50 mmol, 1.00 equiv), cis-DCy-18-C-6 (372.49 mg, 1.00 mmol, 2.0 equiv), C4F9I (1037.79 mg, 3.00 mmol, 6.00 equiv) and DMC (3.0 mL) in the glove box. 2a (240.20 mg, 1.00 mmol, 2.0 equiv) and KF (116.20 mg, 2.00 mmol, 4.00 equiv) were added with stirring at room temperature. The reaction was stirred at 60 °C for 12 h and cooled to room temperature. The solvent was evaporated under vacuum and the crude product was purified by flash column chromatography to give products 3. Yields were listed in Table 5. The ratio of regioisomer ab/ba was determined by 19F NMR spectroscopy.
  • 83
  • [ 175676-42-3 ]
  • 4,5-dimethyl-2-(trimethylsilyl)phenyl triflate [ No CAS ]
  • 2-iodo-4,5-dimethyl-1-(trifluoromethoxy)benzene [ No CAS ]
YieldReaction ConditionsOperation in experiment
44% With potassium fluoride; 1-iodo-2,2,3,3,4,4,5,5,5-nonafluorobutane; cis-dicyclohexano-18-C-6; carbonic acid dimethyl ester at 60℃; for 12h; 3. General Procedure for Trifluoromethoxylation-iodination of Arynes 3a-3m General procedure: To a 15 mL of pressure-proof pipe equipped with a stir bar was added 1 (0.50 mmol, 1.00 equiv), cis-DCy-18-C-6 (372.49 mg, 1.00 mmol, 2.0 equiv), C4F9I (1037.79 mg, 3.00 mmol, 6.00 equiv) and DMC (3.0 mL) in the glove box. 2a (240.20 mg, 1.00 mmol, 2.0 equiv) and KF (116.20 mg, 2.00 mmol, 4.00 equiv) were added with stirring at room temperature. The reaction was stirred at 60 °C for 12 h and cooled to room temperature. The solvent was evaporated under vacuum and the crude product was purified by flash column chromatography to give products 3. Yields were listed in Table 5. The ratio of regioisomer ab/ba was determined by 19F NMR spectroscopy.
  • 84
  • [ 175676-42-3 ]
  • 4,5-dimethoxy-2-(trimethylsilyl)phenyl trifluoromethanesulfonate [ No CAS ]
  • 2-iodo-4,5-dimethoxy-1-(trifluoromethoxy)benzene [ No CAS ]
YieldReaction ConditionsOperation in experiment
45% With potassium fluoride; 1-iodo-2,2,3,3,4,4,5,5,5-nonafluorobutane; cis-dicyclohexano-18-C-6; carbonic acid dimethyl ester at 60℃; for 12h; 3. General Procedure for Trifluoromethoxylation-iodination of Arynes 3a-3m General procedure: To a 15 mL of pressure-proof pipe equipped with a stir bar was added 1 (0.50 mmol, 1.00 equiv), cis-DCy-18-C-6 (372.49 mg, 1.00 mmol, 2.0 equiv), C4F9I (1037.79 mg, 3.00 mmol, 6.00 equiv) and DMC (3.0 mL) in the glove box. 2a (240.20 mg, 1.00 mmol, 2.0 equiv) and KF (116.20 mg, 2.00 mmol, 4.00 equiv) were added with stirring at room temperature. The reaction was stirred at 60 °C for 12 h and cooled to room temperature. The solvent was evaporated under vacuum and the crude product was purified by flash column chromatography to give products 3. Yields were listed in Table 5. The ratio of regioisomer ab/ba was determined by 19F NMR spectroscopy.
  • 85
  • [ 175676-42-3 ]
  • [ 717903-52-1 ]
  • 5-iodo-6-(trifluoromethoxy)benzo[d][1,3]dioxole [ No CAS ]
YieldReaction ConditionsOperation in experiment
62% With potassium fluoride; 1-iodo-2,2,3,3,4,4,5,5,5-nonafluorobutane; cis-dicyclohexano-18-C-6; carbonic acid dimethyl ester at 60℃; for 12h; 3. General Procedure for Trifluoromethoxylation-iodination of Arynes 3a-3m General procedure: To a 15 mL of pressure-proof pipe equipped with a stir bar was added 1 (0.50 mmol, 1.00 equiv), cis-DCy-18-C-6 (372.49 mg, 1.00 mmol, 2.0 equiv), C4F9I (1037.79 mg, 3.00 mmol, 6.00 equiv) and DMC (3.0 mL) in the glove box. 2a (240.20 mg, 1.00 mmol, 2.0 equiv) and KF (116.20 mg, 2.00 mmol, 4.00 equiv) were added with stirring at room temperature. The reaction was stirred at 60 °C for 12 h and cooled to room temperature. The solvent was evaporated under vacuum and the crude product was purified by flash column chromatography to give products 3. Yields were listed in Table 5. The ratio of regioisomer ab/ba was determined by 19F NMR spectroscopy.
  • 86
  • [ 175676-42-3 ]
  • [ 61474-39-3 ]
  • C12H13F3O4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
83% With Co(((CH3)3C)4(C6H2CHNO)2C6H10)OC6H3(NO2)2; tetrabutylammonium 2,4-dinitrophenoxide In acetonitrile at 25℃; for 24h; Sealed tube; Inert atmosphere; Glovebox;
  • 87
  • [ 175676-42-3 ]
  • [ 14700-55-1 ]
  • C11H17F3O4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
90% With Co(((CH3)3C)4(C6H2CHNO)2C6H10)OC6H3(NO2)2; tetrabutylammonium 2,4-dinitrophenoxide In acetonitrile at 25℃; for 24h; Sealed tube; Inert atmosphere; Glovebox;
  • 88
  • [ 175676-42-3 ]
  • [ 57280-22-5 ]
  • C8H13F3O4 [ No CAS ]
  • 89
  • [ 175676-42-3 ]
  • [ 68973-05-7 ]
  • C19H21F3O4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
95% With Co(((CH3)3C)4(C6H2CHNO)2C6H10)OC6H3(NO2)2; tetrabutylammonium 2,4-dinitrophenoxide In acetonitrile at 25℃; for 24h; Sealed tube; Inert atmosphere; Glovebox;
  • 90
  • [ 175676-42-3 ]
  • [ 1689-71-0 ]
  • C15H13F3O2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
85% With Co(((CH3)3C)4(C6H2CHNO)2C6H10)OC6H3(NO2)2; tetrabutylammonium 2,4-dinitrophenoxide In acetonitrile at 25℃; for 24h; Sealed tube; Inert atmosphere; Glovebox;
  • 91
  • [ 175676-42-3 ]
  • [ 31865-25-5 ]
  • C13H14F3NO4 [ No CAS ]
  • 92
  • [ 175676-42-3 ]
  • [ 183065-60-3 ]
  • C9H13F3O4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
87% With Co(((CH3)3C)4(C6H2CHNO)2C6H10)OC6H3(NO2)2; tetrabutylammonium 2,4-dinitrophenoxide In acetonitrile at 25℃; for 24h; Sealed tube; Inert atmosphere; Glovebox;
Same Skeleton Products
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