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[ CAS No. 148438-03-3 ] {[proInfo.proName]}

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Chemical Structure| 148438-03-3
Chemical Structure| 148438-03-3
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Product Details of [ 148438-03-3 ]

CAS No. :148438-03-3 MDL No. :MFCD06802402
Formula : C11H12O2 Boiling Point : -
Linear Structure Formula :- InChI Key :AZIWZLOGNAEWLR-UHFFFAOYSA-N
M.W : 176.21 Pubchem ID :11658370
Synonyms :

Safety of [ 148438-03-3 ]

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

Application In Synthesis of [ 148438-03-3 ]

* 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 [ 148438-03-3 ]

[ 148438-03-3 ] Synthesis Path-Downstream   1~44

  • 1
  • [ 1126-46-1 ]
  • [ 335672-72-5 ]
  • [ 148438-03-3 ]
YieldReaction ConditionsOperation in experiment
With 1,3-bis[2,6-diisopropylphenyl]imidazolium chloride In tetrahydrofuran for 21h; Heating;
  • 2
  • [ 619-42-1 ]
  • [ 411235-57-9 ]
  • 4-cyclopropylbenzoic acid methyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
96% With potassium phosphate; tetrakis(triphenylphosphine) palladium(0) In toluene at 110℃; for 54h; Inert atmosphere;
95% With potassium carbonate In xylene at 130℃; for 20h;
92% With potassium phosphate tribasic heptahydrate; C45H53ClFeNO2PPd In water; toluene at 100℃; for 8h; Inert atmosphere; 4.2. General experimental procedure General procedure: Potassium phosphate (0.75 mmol) and IIe (1 mol %) was added to the solution of aryl halides (0.25 mmol) and cyclopropylboronic acid (0.5 mmol) in toluene (2.0 mL) and water (100 μL). The mixture was heated to 100 °C for a proper time under nitrogen atmosphere and cooled to room temperature. Water (10 mL) was added and the mixture was extracted with EtOAc (3×15 mL), evaporated and purified by chromatography on silica gel.
17% With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In 1,2-dimethoxyethane at 95℃; Sealed tube; Inert atmosphere; 1.17 Step 1: methyl 4-cyclopropylbenzoate Step 1: methyl 4-cyclopropylbenzoate [0232] A mixture of methyl 4-bromobenzoate (5.05 g, 23.6 mmol), cyclopropylboronic acid (10.0 g , 0.12 mol), Pd(PPh3)4 (2.7 g, 2.34 mmol) and saturated sodium carbonate (30 mL, 46 mmol) in DME (100 mL) was heated to 95°C in the sealed tube under N2 atmosphere. After stirring overnightthe mixture was cooled to rt and concentrated. The concentrate was partitioned into DCM and water. The organic phase was washed with water, brine, dried over Na2S04 and concentrated in vacuo. The concentrate was purified by column chromatography over silica gel (hexane/DCM = 10/1) to afford the title compound as a yellow oil (710 mg, 17%). MS (ESI) calcd for CnHi202: 176.0; found: 177.3[M+H]. *H NM (400 MHz, CDCI3) δ 7.91 (d, J = 8.0 Hz, 2H), 7.10(d, J = 8.0 Hz, 2H), 3.89 (s, 3H), 1.97-1.90 (m, 1H), 1.08-1.02 (m, 2H), 0.80-0.74 (m, 2H).

  • 3
  • [ 126403-68-7 ]
  • [ 619-42-1 ]
  • [ 148438-03-3 ]
YieldReaction ConditionsOperation in experiment
70% With (1,2-dimethoxyethane)dichloronickel(II); 4,4'-di-tert-butyl-2,2'-bipyridine In tetrahydrofuran; N,N-dimethyl-formamide at 60℃; for 0.333333h; Irradiation; Flow reactor;
97 %Chromat. With PEPPSI Pd catalyst In tetrahydrofuran at 20℃; for 1h; Inert atmosphere;
  • 4
  • [ 619-42-1 ]
  • [ 23719-80-4 ]
  • [ 148438-03-3 ]
YieldReaction ConditionsOperation in experiment
Stage #1: cyclopropylmagnesium bromide With zinc dibromide In tetrahydrofuran at 0℃; for 0.5h; Inert atmosphere; Stage #2: 4-methoxycarbonylphenyl bromide With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 In tetrahydrofuran at -40 - 20℃; Inert atmosphere; 1 Compound 10.1. Methyl 4-cyclopropylbenzoate Compound 10.1. Methyl 4-cyclopropylbenzoate. Into a 1 -L three neck round- bottom flask, which was purged and maintained with an inert atmosphere of nitrogen, was placed a solution mixture of ZnBr2 (41.5 g, 184 mmol) and tetrahydrofuran (500 mL). The mixture was cooled to 0 °C, then cyclopropylmagnesium bromide (2 M in THF)(92 mL, 184 mmol) was added drop- wise with stirring over 30 min. The mixture was then cooled to -40 °C and Pd(dppf)Cl2 (3.00 g, 4.1 mmol) was added portion- wise over 1 min. Methyl 4- bromobenzoate (10.0 g, 46.50 mmol) in THF (50 mL) was added drop-wise over 30 min at - 40 °C. The resulting mixture was allowed to warm to room temperature and stirred overnight. The reaction was then carefully quenched by the addition of aqueous NH4C1 (sat., 500 mL). The mixture was extracted with ethyl acetate (3 x 300 mL) and the combined organic layers were washed with brine (3 x 300 mL), dried (Na2S04), filtered, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography with petroleum ether as the eluent to yield 8.87 g (crude) of the title compound as a yellow oil.
Stage #1: cyclopropylmagnesium bromide With zinc dibromide In tetrahydrofuran at 0℃; for 0.5h; Inert atmosphere; Stage #2: 4-methoxycarbonylphenyl bromide With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride In tetrahydrofuran at -40 - 20℃; Compound 10.1. Methyl 4-cyclopropylbenzoate Compound 10.1. Methyl 4-cyclopropylbenzoate. Into a 1-L three neck round- bottom flask, which was purged and maintained with an inert atmosphere of nitrogen, was placed a solution mixture of ZnBr2 (41.5 g, 184 mmol) and tetrahydrofuran (500 mL). The mixture was cooled to 0 °C, then cyclopropylmagnesium bromide (2 M in THF)(92 mL, 184 mmol) was added drop-wise with stirring over 30 min. The mixture was then cooled to -40 °C and Pd(dppf)Ci2 (3.00 g, 4.1 mmol) was added portion- wise over 1 min. Methyl 4- bromobenzoate (10.0 g, 46.50 mmol) in THF (50 mL) was added drop-wise over 30 min at - 40 °C. The resulting mixture was allowed to warm to room temperature and stirred overnight. The reaction was then carefully quenched by the addition of aqueous NH4C1 (sat., 500 mL). The mixture was extracted with ethyl acetate (3 x 300 mL) and the combined organic layers were washed with brine (3 x 300 mL), dried ( a2S04), filtered, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography with petroleum ether as the eluent to yield 8.87 g (crude) of the title compound as a yellow oil.
  • 5
  • [ 148438-03-3 ]
  • [ 1131615-05-8 ]
YieldReaction ConditionsOperation in experiment
0.5 g With N-Bromosuccinimide; trifluoroacetic acid at 50℃; 1 Compound 10.2. Methyl 3-bromo-4-cyclopropylbenzoate. Compound 10.2. Methyl 3-bromo-4-cyclopropylbenzoate. Into a 50-mL round- bottom flask, was placed a mixture of methyl 4-cyclopropylbenzoate (compound 10.1, 500 mg, 2.84 mmol), N-bromosuccinimide (500 mg, 2.81 mmol) and trifluoroacetic acid (20 mL). The mixture was stirred overnight at 50 °C, then cooled and carefully quenched with water (10 mL). The mixture was extracted with ethyl acetate (3 x 30 mL) and the combined organic layers were washed with brine (3 x 30 mL), dried (Na2S04), filtered, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography with petroleum ether as the eluent to yield 0.5 g (69%) of the title compound as a yellow oil.
0.5 g With N-Bromosuccinimide; trifluoroacetic acid at 50℃; Compound 10.2. Methyl 3-bromo-4-cyclopropylbenzoate Compound 10.2. Methyl 3-bromo-4-cyclopropylbenzoate. Into a 50-mL round- bottom flask, was placed a mixture of methyl 4-cyclopropylbenzoate (compound 10.1, 500 mg, 2.84 mmol), N-bromosuccinimide (500 mg, 2.81 mmol) and trifluoroacetic acid (20 mL). The mixture was stirred overnight at 50 °C, then cooled and carefully quenched with water (10 mL). The mixture was extracted with ethyl acetate (3 x 30 mL) and the combined organic layers were washed with brine (3 x 30 mL), dried ( a2S04), filtered, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography with petroleum ether as the eluent to yield 0.5 g (69%) of the title compound as a yellow oil.
  • 6
  • 4-cyclopropylbenzoic acid methyl ester [ No CAS ]
  • [ 1131622-50-8 ]
  • 7
  • [ 148438-03-3 ]
  • [ 1533440-50-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: trifluoroacetic acid; N-Bromosuccinimide / 50 °C 2.1: water; sodium hydroxide / methanol / 50 °C 3.1: n-butyllithium / tetrahydrofuran; diethyl ether / 0.5 h / -78 °C / Inert atmosphere 3.2: 2 h / -78 °C / Inert atmosphere
Multi-step reaction with 3 steps 1.1: N-Bromosuccinimide; trifluoroacetic acid / 50 °C 2.1: sodium hydroxide / methanol; water / 50 °C 3.1: n-butyllithium / tetrahydrofuran; diethyl ether / 0.5 h / -78 °C / Inert atmosphere 3.2: 2 h / -78 °C
  • 8
  • [ 148438-03-3 ]
  • [ CAS Unavailable ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: trifluoroacetic acid; N-Bromosuccinimide / 50 °C 2.1: water; sodium hydroxide / methanol / 50 °C 3.1: n-butyllithium / tetrahydrofuran; diethyl ether / 0.5 h / -78 °C / Inert atmosphere 3.2: 2 h / -78 °C / Inert atmosphere 4.1: tetrahydrofuran; diethyl ether / 2.25 h / 20 °C / Inert atmosphere
Multi-step reaction with 4 steps 1.1: N-Bromosuccinimide; trifluoroacetic acid / 50 °C 2.1: sodium hydroxide / methanol; water / 50 °C 3.1: n-butyllithium / tetrahydrofuran; diethyl ether / 0.5 h / -78 °C / Inert atmosphere 3.2: 2 h / -78 °C 4.1: tetrahydrofuran; diethyl ether / 2.25 h / 20 °C / Inert atmosphere
  • 9
  • [ 148438-03-3 ]
  • [ 1533440-55-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1.1: trifluoroacetic acid; N-Bromosuccinimide / 50 °C 2.1: water; sodium hydroxide / methanol / 50 °C 3.1: n-butyllithium / tetrahydrofuran; diethyl ether / 0.5 h / -78 °C / Inert atmosphere 3.2: 2 h / -78 °C / Inert atmosphere 4.1: tetrahydrofuran; diethyl ether / 2.25 h / 20 °C / Inert atmosphere 5.1: Dess-Martin periodane / 1,2-dichloro-ethane / 1.5 h / 20 °C
Multi-step reaction with 5 steps 1.1: N-Bromosuccinimide; trifluoroacetic acid / 50 °C 2.1: sodium hydroxide / methanol; water / 50 °C 3.1: n-butyllithium / tetrahydrofuran; diethyl ether / 0.5 h / -78 °C / Inert atmosphere 3.2: 2 h / -78 °C 4.1: tetrahydrofuran; diethyl ether / 2.25 h / 20 °C / Inert atmosphere 5.1: Dess-Martin periodane / 1,2-dichloro-ethane / 1.5 h / 20 °C
  • 10
  • [ 148438-03-3 ]
  • [ 1533440-56-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1.1: trifluoroacetic acid; N-Bromosuccinimide / 50 °C 2.1: water; sodium hydroxide / methanol / 50 °C 3.1: n-butyllithium / tetrahydrofuran; diethyl ether / 0.5 h / -78 °C / Inert atmosphere 3.2: 2 h / -78 °C / Inert atmosphere 4.1: tetrahydrofuran; diethyl ether / 2.25 h / 20 °C / Inert atmosphere 5.1: Dess-Martin periodane / 1,2-dichloro-ethane / 1.5 h / 20 °C 6.1: potassium carbonate / N,N-dimethyl-formamide / 1 h / 0 - 10 °C
Multi-step reaction with 6 steps 1.1: N-Bromosuccinimide; trifluoroacetic acid / 50 °C 2.1: sodium hydroxide / methanol; water / 50 °C 3.1: n-butyllithium / tetrahydrofuran; diethyl ether / 0.5 h / -78 °C / Inert atmosphere 3.2: 2 h / -78 °C 4.1: tetrahydrofuran; diethyl ether / 2.25 h / 20 °C / Inert atmosphere 5.1: Dess-Martin periodane / 1,2-dichloro-ethane / 1.5 h / 20 °C 6.1: potassium carbonate / N,N-dimethyl-formamide / 1 h / 0 - 10 °C
YieldReaction ConditionsOperation in experiment
95% With bis(tri-ortho-tolylphosphine)palladium(0); silver(l) oxide In tetrahydrofuran at 85℃; for 24h; Inert atmosphere; Sealed tube; 6 Example 5. (S)-l-(sec-butyl)-4-(tert-but l)benzene (3f) General procedure: General procedure of coupling reactions of aryl halides with alk l boronic acids In the glove box under argon atmosphere, aryl halide (0.10 mmol), boronic acid (0.20 mmol), Ag20 (70 mg, 0.30 mmol) and Pd(P(o-tol)3)2 (7.15 mg, 0.010 mmol) were taken up in THF (220 μ) in a 7-mL vial. The reaction was sealed, and stirred at 85 °C for 24 h. The mixture was then passed through a pad of silica gel and flushed with diethyl ether before concentration in vacuo. The desired product was isolated by column chromatography and/or preparative reverse-phase HPLC. Cross-coupling reactions of aryl halides with alkyl boronic acids Example 5. (S)-l-(sec-butyl)-4-(tert-but l)benzene (3f) Product was isolated as a colorless oil (Br-, 31%>; I-, 61%>) 1H NMR (499 MHz, Benzene) δ 7.31 (d, J= 8.5, 2H), 7.11 (d, J= 8.5, 2H), 2.489 (m, lH), 2.47 (m, 1H), 1.504 (m, 1H), 1.258 (s, 9H), 1.20 (d, J= 7.0, 3H), 0.81 (t, J= 7.5, 3H). 13C NMR (126 MHz, Benzene) δ 148.6, 144.7, 127.1, 125.5, 41.6, 34.4, 31.6, 31.6, 22.3, 12.5. HRMS (EI+) Calculated for Ci2H22: 190.1722 Found: 190.1727
  • 12
  • [ 96-09-3 ]
  • [ 148438-03-3 ]
  • [ 1854998-24-5 ]
YieldReaction ConditionsOperation in experiment
60% With dimanganese decacarbonyl; triphenylborane In hexane; 1,2-dichloro-ethane at 150℃; for 24h; Sealed tube; Inert atmosphere;
  • 13
  • [ 75-09-2 ]
  • [ 1076-96-6 ]
  • [ 148438-03-3 ]
YieldReaction ConditionsOperation in experiment
With [i-PrNDI]Ni2(C6H6); zinc In N,N-dimethyl acetamide at 22℃; for 65h; Inert atmosphere; Glovebox; Sealed tube;
  • 14
  • [ 4333-56-6 ]
  • [ 619-42-1 ]
  • [ 148438-03-3 ]
YieldReaction ConditionsOperation in experiment
72% With 2,6-dimethylpyridine; tris-(trimethylsilyl)silane; (4-methoxyphenyl)(4-(trifluoromethyl)phenyl)methanone; (dtbbpy)NiBr2 In acetonitrile at 20℃; for 0.75h; UV-irradiation;
32% With [4,4′-bis(1,1-dimethylethyl)-2,2′-bipyridine]nickel(II) dichloride; tris-(trimethylsilyl)silane; [Ir(dF(CF3)ppy)2(dtbbpy)]PF6; anhydrous sodium carbonate In ethylene glycol dimethyl ether at 20℃; for 6h; Inert atmosphere; Irradiation;
  • 15
  • 4-cyclopropylbenzoic acid methyl ester [ No CAS ]
  • [ 454678-87-6 ]
YieldReaction ConditionsOperation in experiment
83% With lithium aluminium tetrahydride; In tetrahydrofuran; at 0℃; for 1h;Inert atmosphere; Step 2: (4-cyclopropylphenyl)methanol [0233] A solution of methyl 4-cyclopropylbenzoate (710 mg, 4.0 mmol) in dry THF was added dropwise to a suspension of LiAIH4 in THF (20 mL) at 0 C under N2 atmosphere. The reaction mixture was stirred for lh, then quenched by addition of Na2SO4.10H2O under ice-water bath cooling. The mixture was stirred at rt for 30 min, and filtered through celite. The filter mass was extracted with EtOAc. The combined filtrate and organic extracts were dried over Na2S04 and concentrated to afford the title compound as a brown oil (500 mg, 83%). H NM (400 M Hz, CDCI3) δ 7.26 (d , J Hz, 2H), 7.07 (d, J = 8.0 Hz, 2H), 4.64 (s, 2H), 1.94-1.85 (m, 1H), 0.98-0.93 (m, 2H), 0.70-0.66 (m,
  • 16
  • [ 148438-03-3 ]
  • [ 1952293-98-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / 0 °C / Inert atmosphere 2.1: dimethyl sulfoxide / 1 h / 20 °C 2.2: 50 °C / Inert atmosphere; Sealed tube
  • 17
  • [ 148438-03-3 ]
  • [ 1952294-45-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / 0 °C / Inert atmosphere 2.1: dimethyl sulfoxide / 1 h / 20 °C 2.2: 50 °C / Inert atmosphere; Sealed tube 3.1: methanol / 0.5 h
  • 18
  • [ 148438-03-3 ]
  • [ 1952294-08-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / 0 °C / Inert atmosphere 2.1: dimethyl sulfoxide / 1 h / 20 °C 2.2: 50 °C / Inert atmosphere; Sealed tube
  • 19
  • [ 148438-03-3 ]
  • [ 1952294-46-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / 0 °C / Inert atmosphere 2.1: dimethyl sulfoxide / 1 h / 20 °C 2.2: 50 °C / Inert atmosphere; Sealed tube 3.1: methanol / 0.5 h
  • 20
  • [ 925430-09-7 ]
  • [ CAS Unavailable ]
  • [ 619-44-3 ]
  • [ 1400701-82-7 ]
  • [ 148438-03-3 ]
YieldReaction ConditionsOperation in experiment
1: 46.2 mg 2: 1.0 mg With (η3-allyl)(N,N'-bis(2,6-diisopropylphenyl)-4,5-dihydroimidazol-2-ylidene)chloropalladium(II); sodium carbonate; lithium chloride In N,N-dimethyl-formamide at 40℃; for 16h; Inert atmosphere; Sealed tube; 5. General procedure for the carbonylative cross-coupling General procedure: Method A: A sealed tube equiped with a magnetic stirring bar was charged with the arylhalide (1) or (5) (1.0 equiv), sodium carbonate (2.0 equiv), anhydrous lithium chloride (2.0equiv) and (SIPr)Pd(allyl)Cl (0.05 equiv). Tricyclopropylbismuth (2a) (1.0 equiv), preparedas described above, was dissolved in anhydrous DMF (0.1 M) under argon and was addedinto the sealed tube. Carbon monoxide was bubbled in the reaction mixture for 45 seconds,then the tube was sealed and heated at 40 °C for 16 hours. The reaction mixture was cooledto room temperature, transferred in a separatory funnel containing 20 mL of an aq. sat.NaHCO3 solution and was extracted with EtOAc (3 x 20 mL). The combined organic layerswere washed with brine (30 mL), dried over anhydrous Na2SO4 and concentrated underreduced pressure. The residue was purified by flash column chromatography using theindicated solvent system to afford the desired aryl cyclopropyl ketone (3) or (6).Method B: Same as method A except that 1.5 equivalents of tricyclopropylbismuth 2ainstead of 1.0 equivalent and 0.1 equivalents of (SIPr)Pd(allyl)Cl instead of 0.05 equivalentswere used and that the reaction was heated at 80 C instead of 40 C.
  • 22
  • [ 148438-03-3 ]
  • [ 2414143-31-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: sodium hexamethyldisilazane / tetrahydrofuran / 6 h / 0 - 20 °C 2: tetrakis(triphenylphosphine) palladium(0); sodium hydrogencarbonate / water; 1,2-dimethoxyethane / 5 h / 80 °C
  • 23
  • [ 148438-03-3 ]
  • [ 2414143-02-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: sodium hexamethyldisilazane / tetrahydrofuran / 6 h / 0 - 20 °C 2: bis-triphenylphosphine-palladium(II) chloride; sodium carbonate / water; 1,2-dimethoxyethane / 4 h / 85 °C
  • 24
  • [ 148438-03-3 ]
  • [ 2414143-80-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: sodium hexamethyldisilazane / tetrahydrofuran / 6 h / 0 - 20 °C 2: bis-triphenylphosphine-palladium(II) chloride; sodium carbonate / water; 1,2-dimethoxyethane / 4 h / 85 °C 3: trifluoroacetic acid / 1,2-dichloro-ethane / 36 h / 80 °C
  • 25
  • [ 148438-03-3 ]
  • [ 2414144-61-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: sodium hexamethyldisilazane / tetrahydrofuran / 6 h / 0 - 20 °C 2: bis-triphenylphosphine-palladium(II) chloride; sodium carbonate / water; 1,2-dimethoxyethane / 4 h / 85 °C 3: trifluoroacetic acid / 1,2-dichloro-ethane / 36 h / 80 °C 4: triethylamine / dichloromethane / 1.5 h / -10 - 20 °C
  • 26
  • [ 148438-03-3 ]
  • [ 2414144-63-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: sodium hexamethyldisilazane / tetrahydrofuran / 6 h / 0 - 20 °C 2: bis-triphenylphosphine-palladium(II) chloride; sodium carbonate / water; 1,2-dimethoxyethane / 4 h / 85 °C
  • 27
  • [ 148438-03-3 ]
  • [ 2414143-21-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: sodium hexamethyldisilazane / tetrahydrofuran / 6 h / 0 - 20 °C 2: bis-triphenylphosphine-palladium(II) chloride; sodium carbonate / water; 1,2-dimethoxyethane / 4 h / 85 °C 3: trifluoroacetic acid / 1,2-dichloro-ethane / 36 h / 80 °C
  • 28
  • [ 148438-03-3 ]
  • [ 2414143-52-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: sodium hexamethyldisilazane / tetrahydrofuran / 6 h / 0 - 20 °C 2: bis-triphenylphosphine-palladium(II) chloride; sodium carbonate / water; 1,2-dimethoxyethane / 4 h / 85 °C 3: trifluoroacetic acid / 1,2-dichloro-ethane / 36 h / 80 °C 4: triethylamine / dichloromethane / 1.5 h / -10 - 20 °C
  • 29
  • [ 148438-03-3 ]
  • [ 2459286-40-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: sodium hexamethyldisilazane / tetrahydrofuran / 6 h / 0 - 20 °C 2: bis-triphenylphosphine-palladium(II) chloride; sodium carbonate / water; 1,2-dimethoxyethane / 24 h / 85 °C
  • 30
  • [ 148438-03-3 ]
  • [ 2414143-72-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: sodium hexamethyldisilazane / tetrahydrofuran / 6 h / 0 - 20 °C 2: bis-triphenylphosphine-palladium(II) chloride; sodium carbonate / water; 1,2-dimethoxyethane / 24 h / 85 °C 3: trifluoroacetic acid / dichloromethane / 4 h / 20 °C
  • 31
  • [ 148438-03-3 ]
  • [ 2414142-74-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: sodium hexamethyldisilazane / tetrahydrofuran / 6 h / 0 - 20 °C 2: bis-triphenylphosphine-palladium(II) chloride; sodium carbonate / water; 1,2-dimethoxyethane / 24 h / 85 °C 3: trifluoroacetic acid / dichloromethane / 4 h / 20 °C 4: triethylamine / dichloromethane / 1 h / -10 - 20 °C
  • 32
  • [ 148438-03-3 ]
  • [ 2459286-41-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: sodium hexamethyldisilazane / tetrahydrofuran / 6 h / 0 - 20 °C 2: bis-triphenylphosphine-palladium(II) chloride; sodium carbonate / water; 1,2-dimethoxyethane / 16 h / 85 °C / Inert atmosphere
  • 33
  • [ 148438-03-3 ]
  • [ 2414143-99-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: sodium hexamethyldisilazane / tetrahydrofuran / 6 h / 0 - 20 °C 2: bis-triphenylphosphine-palladium(II) chloride; sodium carbonate / water; 1,2-dimethoxyethane / 16 h / 85 °C / Inert atmosphere 3: trifluoroacetic acid / dichloromethane / 6 h / 20 °C
  • 34
  • [ 148438-03-3 ]
  • [ 2414144-53-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: sodium hexamethyldisilazane / tetrahydrofuran / 6 h / 0 - 20 °C 2: bis-triphenylphosphine-palladium(II) chloride; sodium carbonate / water; 1,2-dimethoxyethane / 16 h / 85 °C / Inert atmosphere 3: trifluoroacetic acid / dichloromethane / 6 h / 20 °C 4: triethylamine / dichloromethane / 1.5 h / -10 - 20 °C
  • 37
  • [ 148438-03-3 ]
  • [ 2411970-11-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: hydrazine hydrate / ethanol; toluene / 16 h / 70 °C 2: N-ethyl-N,N-diisopropylamine / dichloromethane / 1 h / 0 - 20 °C
  • 38
  • [ CAS Unavailable ]
  • [ 2093132-18-2 ]
  • [ 148438-03-3 ]
  • [ 2618460-69-6 ]
YieldReaction ConditionsOperation in experiment
10 %Spectr. With copper (I) trifluoromethane sulfonate toluene complex; zinc trifluoromethanesulfonate; lithium dimethylacetate In 1,2-dichloro-ethane at 20℃; for 24h; Inert atmosphere; Sealed tube; Glovebox; regioselective reaction;
  • 39
  • [ CAS Unavailable ]
  • [ 133745-75-2 ]
  • [ 148438-03-3 ]
  • [ 2618460-60-7 ]
YieldReaction ConditionsOperation in experiment
12% With zinc trifluoromethanesulfonate; copper(II) bis(trifluoromethanesulfonate); lithium dimethylacetate at 20℃; for 24h; Inert atmosphere; Sealed tube; Glovebox; regioselective reaction;
  • 40
  • [ 153170-84-4 ]
  • [ CAS Unavailable ]
  • [ 148438-03-3 ]
  • [ 2618460-61-8 ]
YieldReaction ConditionsOperation in experiment
48% With zinc trifluoromethanesulfonate; copper(II) bis(trifluoromethanesulfonate); lithium dimethylacetate at 20℃; for 24h; Inert atmosphere; Sealed tube; Glovebox; regioselective reaction;
  • 41
  • [ 153170-86-6 ]
  • [ CAS Unavailable ]
  • [ 148438-03-3 ]
  • [ 2618460-68-5 ]
YieldReaction ConditionsOperation in experiment
40 %Spectr. With copper (I) trifluoromethane sulfonate toluene complex; zinc trifluoromethanesulfonate; lithium dimethylacetate In 1,2-dichloro-ethane at 20℃; for 24h; Inert atmosphere; Sealed tube; Glovebox; regioselective reaction;
  • 42
  • [ 133745-75-2 ]
  • [ 148438-03-3 ]
  • [ 2737304-65-1 ]
  • [ CAS Unavailable ]
YieldReaction ConditionsOperation in experiment
81.818 % de With dipotassium peroxodisulfate; copper(l) iodide; sodium hydrogencarbonate; magnesium bromide at 150℃; for 20h; Schlenk technique; Sealed tube; Overall yield = 76 percent; Overall yield = 35.8 mg; 2.2 Preparation of allylaminations General procedure: A 20 mL of Schlenk tube equipped with a stir bar was charged with cyclopropylbenzene (0.1 mmol, 1.0 equiv.), N-fluoro-N-(phenylsulfonyl)benzenesulfonamide (0.2 mmol, 2.0 equiv.), CuI (2.0 mg, 10 mol %), MgBr2 (9.2 mg, 50 mol %), K2S2O8 (40.5 mg, 1.5 equiv.), NaHCO3 (25.2 mg, 3 equiv.) and PhCF3 (1 mL). The tube was sealed with a PTFE cap. The reaction mixture was stirred at 150 °C for 20 h under air in an oil bath. After the completion of the reaction, the mixture was then allowed to cool to room temperature. The organic solution was concentrated, and purified through silica gel column chromatography using a mixture of ethyl acetate (EtOAc) and petroleum ether (PE) as eluent to afford the corresponding products.
  • 43
  • [ 403-33-8 ]
  • [ 411235-57-9 ]
  • [ 148438-03-3 ]
YieldReaction ConditionsOperation in experiment
With potassium phosphate; palladium diacetate; tricyclohexylphosphine In water; toluene at 100℃; for 12h; Inert atmosphere; 2.1 Preparation of substrates (3c-3p) General procedure: The substrates from 3c to 3p were prepared according to the published procedures.1, 2 A flame-dried three-neck flask equipped with a stir bar and a reflux condenser was added with substituted bromobenzene (8.95 mmol), cyclopropylboronic acid (1.00 g, 11.6 mmol), and K3PO4 (6.5 g, 31.3 mmol) in toluene (30 mL) and H2O (2 mL) under N2. After the mixture was stirred, 10 wt. % solution of PCy3 in toluene (2.5 mL, 1.8 mmol) was then added via syringe, followed by Pd(OAc)2 (0.101 g, 0.45 mmol). The reaction mixture was heated to 100 oC overnight. After removing from heat, the reaction mixture was diluted with H2O and extracted into EtOAc. The combined organic layers were washed with brine, dried with NaSO4, filtered through Celite, and concentrated. Arylcyclopropane products were purified via column chromatography.
  • 44
  • [ 133745-75-2 ]
  • [ CAS Unavailable ]
  • [ 148438-03-3 ]
  • [ 74-11-3 ]
  • [ 2862775-93-5 ]
YieldReaction ConditionsOperation in experiment
37 % With lithium tert-butoxide at 40℃; Inert atmosphere;
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