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[ CAS No. 1205-39-6 ]

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2D
Chemical Structure| 1205-39-6
Chemical Structure| 1205-39-6
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Product Details of [ 1205-39-6 ]

CAS No. :1205-39-6MDL No. :MFCD01318642
Formula :C13H13NBoiling Point :-
Linear Structure Formula :-InChI Key :N/A
M.W :183.25Pubchem ID :10986946
Synonyms :

Computed Properties of [ 1205-39-6 ]

TPSA : 12 H-Bond Acceptor Count : 1
XLogP3 : - H-Bond Donor Count : 1
SP3 : 0.08 Rotatable Bond Count : 2

Safety of [ 1205-39-6 ]

Signal Word:WarningClassN/A
Precautionary Statements:P261-P305 P351 P338UN#:N/A
Hazard Statements:H315-H319-H335Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 1205-39-6 ]

  • Upstream synthesis route of [ 1205-39-6 ]
  • Downstream synthetic route of [ 1205-39-6 ]

[ 1205-39-6 ] Synthesis Path-Upstream   1~62

  • 1
  • [ 16419-60-6 ]
  • [ 62-53-3 ]
  • [ 1205-39-6 ]
YieldReaction ConditionsOperation in experiment
95% With potassium carbonate In water at 20℃; General procedure: In a typical example, phenylboronic acid 1 (1.22 g, 1 mmol) was charged in the flask containing K2CO3 (2 equiv) in water as solvent (2 mL). To this was added aniline 2 (0.93 g, 1 mmol) and Cu–Mn catalyst, and the reaction mixture was allowed to stir at room temperature. The completion of the reaction was monitored by TLC. After completion, the base was neutralized using 2 N HCl and the catalyst was filtered off, thorough washings of water were given, extracted with ethyl acetate, and the organic layer was separated and dried under reduced vacuum. The crude product obtained was purified on silica gel column chromatography (solvents, ratio?), to obtain white crystalline product diphenylamine 3a (1.60 g) with 95percent yield. All reactions were similarly carried out.
88% With potassium carbonate In water at 20℃; for 5.00 h; General procedure: To a stirred solution of phenylboronic acid (1.0 mmol), aniline (1.0 mmol), and K2CO3 (2.0 mmol) in deionized H2O (10 mL) at room temperature was added an aqueous suspension of FePd nanowires (3.0 mol percent in 3 mL of H2O). The mixture was stirred at room temperature for 5h. After completion of the reaction (as monitored by TLC), 2 M HCl was added and the catalyst was separated by applying an external magnet. The catalyst was washed with EtOAc. The mixture was extracted with EtOAc (2 * 20 mL), dried, and concentrated. The residue was subjected to gel permeation chromatography to afford pure product.
Reference: [1] Tetrahedron Letters, 2013, vol. 54, # 39, p. 5351 - 5354
[2] RSC Advances, 2014, vol. 4, # 90, p. 49273 - 49279
[3] Bulletin of the Korean Chemical Society, 2012, vol. 33, # 5, p. 1785 - 1787
[4] Journal of Organic Chemistry, 2006, vol. 71, # 25, p. 9522 - 9524
[5] Tetrahedron Letters, 2014, vol. 55, # 17, p. 2813 - 2817
[6] RSC Advances, 2014, vol. 4, # 43, p. 22775 - 22778
[7] Organic Letters, 2012, vol. 14, # 17, p. 4326 - 4329
[8] Organic letters, 2001, vol. 3, # 13, p. 2077 - 2079
  • 2
  • [ 95-53-4 ]
  • [ 98-80-6 ]
  • [ 1205-39-6 ]
YieldReaction ConditionsOperation in experiment
76% With N-(pyrid-2-yl)benzamide; nickel(II) acetate tetrahydrate; N,N,N',N'-tetramethylguanidine In toluene at 60℃; for 24.00 h; General procedure: The 25 mL RB flask was charged with arylboronic acid (1 mmol), N-nucleophile (2 mmol), Ni(OAc)2*4H2O/1a (10 mol percent of Ni(II) salt and 20 mol percent of 1a), TMG (2 mmol), and toluene (1 ml). The reaction mixture was stirred at 60 °C for 24 h. After completion of the reaction, the reaction mixture was cooled to room temperature, diluted with ethyl acetate (20 mL), and washed with brine water. The combined organic phase was dried over anhydrous Na2SO4. After removal of the solvent, the residue was subjected to column chromatography on silica gel using hexane to afford the Chan-Lam product in high purity.
Reference: [1] RSC Advances, 2014, vol. 4, # 90, p. 49273 - 49279
[2] European Journal of Organic Chemistry, 2011, # 33, p. 6656 - 6662
[3] Tetrahedron Letters, 2015, vol. 56, # 48, p. 6685 - 6688
[4] RSC Advances, 2014, vol. 4, # 43, p. 22775 - 22778
[5] Organic Letters, 2012, vol. 14, # 17, p. 4326 - 4329
  • 3
  • [ 95-46-5 ]
  • [ 62-53-3 ]
  • [ 1205-39-6 ]
YieldReaction ConditionsOperation in experiment
96% With bis[chloro(1,2,3-trihapto-allylbenzene)palladium(II)]; C40H43BN2P(1-)*C16H32LiO4(1+); potassium <i>tert</i>-butylate In tolueneInert atmosphere; Schlenk technique General procedure: Typically, [Pd(cinnamyl)Cl]2 (0.0031 g, 0.006 mmol), ligand 1 (0.0107 mg, 0.012 mmol), and KO(t-Bu) (0.081 g, 0.72 mmol) were loaded into a Schlenk tube. If a solid aryl bromide or amine was used, it was also added at this time. To the mixture of solids, the aryl bromide (0.6 mmol) and amine (0.72 mmol) were added via syringe (if liquid), followed by toluene (2 mL). The resulting mixture was stirred at room temperature for 1 min., then placed in a pre-heated, 80 °C oil bath and allowed to react for 12 h. After this time, the mixture was removed from the bath and cooled to room temperature, diluted with EtOAc (5 mL), and filtered through silica (1 × 4 cm column, ~10 mL), eluting with EtOAc (20 mL) or until the filtrate ran clear. The volatiles were removed from the filtrate via rotary evaporation and the resulting residue was subjected to flash chromatography on silica gel (8 × 2 cm column, ~25 mL silica). Specific details related to the synthesis, yield and characterization of each coupled product are described below in Section 4.8.
82% With bis-triphenylphosphine-palladium(II) chloride; triphenylphosphine; sodium t-butanolate In o-xylene for 12.00 h; Inert atmosphere; Reflux; Schlenk technique General procedure: In a Schlenk tube with a magnetic bar, base (3.0mmol), PdCl2(Ph3P)2 (3.5mg, 0.5molpercent)and Ph3P (2.6mg, 1.0molpercent), aryl amine (1.0mmol), and aryl bromide (2.5mmol) in o-xylene (8.0mL) were placed under nitrogen. The resulting mixture was stirred at reflux for 8h (or 12h) under nitrogen. The solvent was evaporated in vacuo, and the residue was purified by flash column chromatography (petroleum ether/EtOAc) to give the product.
49% With tri-tert-butyl phosphine; palladium diacetate; sodium t-butanolate In toluene at 120℃; for 8.00 h; Inert atmosphere Under a nitrogen atmosphere,25 g of 2-bromotoluene and 40 g of aniline were dissolved in 200 ml of dehydrated toluene, 0.5 g of palladium acetate, 27 g of sodium t-butoxide and 1.4 g of tri-t-butylphosphine were added and the mixture was heated at 120 ° C. for 8 hours. After the reaction, water was added, the organic layer and the aqueous layer were separated with a separating funnel, and the organic layer was concentrated. The crude product was purified on a silica gel short column (solvent: toluene)19 g (yield 49percent) of the following target compound was obtained.
Reference: [1] Journal of Organic Chemistry, 2010, vol. 75, # 19, p. 6477 - 6488
[2] Chemical Communications, 2016, vol. 52, # 12, p. 2612 - 2615
[3] Journal of Organometallic Chemistry, 2017, vol. 841, p. 57 - 61
[4] European Journal of Organic Chemistry, 2016, vol. 2016, # 10, p. 1908 - 1914
[5] Tetrahedron Letters, 2004, vol. 45, # 45, p. 8319 - 8321
[6] Journal of Organic Chemistry, 2011, vol. 76, # 19, p. 7918 - 7932
[7] Journal of Organic Chemistry, 2002, vol. 67, # 18, p. 6479 - 6486
[8] Tetrahedron, 2008, vol. 64, # 29, p. 6920 - 6934
[9] Tetrahedron, 2014, vol. 70, # 32, p. 4754 - 4759
[10] Journal of Organic Chemistry, 2006, vol. 71, # 14, p. 5117 - 5125
[11] New Journal of Chemistry, 2016, vol. 40, # 8, p. 6986 - 6997
[12] Patent: JP5824827, 2015, B2. Location in patent: Paragraph 0152; 0153
[13] European Journal of Organic Chemistry, 2014, vol. 2014, # 10, p. 2070 - 2076
  • 4
  • [ 95-49-8 ]
  • [ 62-53-3 ]
  • [ 1205-39-6 ]
YieldReaction ConditionsOperation in experiment
99% With C28H29Cl2N3OPd; potassium <i>tert</i>-butylate In toluene at 110℃; for 15.00 h; Schlenk technique; Inert atmosphere General procedure: A Schlenk ask was charged with the required aryl chloride (0.25 mmol), amine (0.30 mmol), N-heterocyclic carbene–palladium(II) complex (2 molpercent), KOtBu (1.3 equiv), and toluene (0.5 mL). The mixture was stirred at 110 C for 15 h under N2. After cooling, the mixture was evaporated and the product was isolated by preparative TLC on silica gel plates. The puried products were identied by 1H NMR spectra, and their analytical data are given in the Supporting Information.
97% With [1,3-bis(2,6-diisopropylphenyl)imidazol-2-yl-isoquinolin-2-yl]palladium dichloride; potassium <i>tert</i>-butylate In 1,4-dioxane at 110℃; for 24.00 h; The general reaction conditions: 1, 4 - dioxane (0.5 ml) in, will aryl chloride (0.7mmol), level aromatic amine (1.2equiv. , Relative to the aryl chloride) butyl potassium (1.3equiv. , Relative to the aryl chloride) complex (41), reaction 1 - 24 hours. Yield rate of the product after separation and purification. The following product 53a - 53r in, the right half part of the aryl group is derived from the aromatic amine compound.
95% With C33H40ClN3O2Pd; potassium <i>tert</i>-butylate In toluene at 130℃; for 24.00 h; Inert atmosphere; Schlenk technique; Sealed tube General procedure: Under a N2 atmosphere, KOtBu (102.1 mg, 1.3 equiv) and a so-lution of complex 3a (10e50 mL, 0.01e0.05 molpercent, prepared from4.6 mg of complex 3a in 1.0 mL dichloromethane) were added into aSchlenk reaction tube. The tube was sealed and the solvent wasremoved under reduced pressure. Then toluene (0.5 mL), amines(0.84 mmol) and aryl chlorides (0.70 mmol) were successivelyadded. The mixture was stirred vigorously at the specied tem-perature for 3e24 h. Then the solvent was removed under reducedpressure and the residue was puried by ash column chroma-tography (SiO2) to give the corresponding products.
94% With sodium t-butanolate In toluene at 110℃; for 20.00 h; Example 9General Procedure for Pd-Catalysed Amination Reactions[0045] The phosphine ligand compounds of the present invention can be used in conjunction with transition metal catalysts employed in the animation of aryl chlorides. Pd- catalyzed amination of aryl halides has become a powerful method for the synthesis of aniline derivatives. Employing readily available aryl chlorides in this transformation has also become a focus and met with moderate success in recent years. EPO <DP n="30"/>[0046] The procedure for the animation reaction using an unactivated aryl chloride in the presence of a transition metal catalyst and a phosphine ligand is as follows. A Schlenk tube, which was flame-dried under vaccum and backfilled with nitrogen, was charged with an amine (1.2 mmol) and a base such as KO(t-Bu) or NaO(t-Bu) (1.2 equiv.). The flask was evacuated and backfilled with nitrogen three times. Toluene (3 mL), a stock solution of a phosphine ligand (1.0-2.0 molpercent) in toluene, a stock solution of a Pd catalyst (0.5-1.0 molpercent) in toluene, and aryl chloride (1.0 mmol) were subsequently added. The flask was sealed and the reaction mixture was heated to 80°C or 110°C with vigorous stirring for 20-24 hours. After cooling to room temperature, 10 mL of EtOAc was added and the mixture was washed with 10 mL of 1N NaOH (aq.) and 10 mL of brine. The organic layer was dried over Na2SO4 and concentrated under reduced pressure. The crude product was purified by flash column chromatography on silica gel. The yields of the amination reaction using phosphine ligands described in this example coupled with Pd catalyst are summarized forth in Table 4 below. EPO <DP n="31"/>TABLE 4 EPO <DP n="32"/> EPO <DP n="33"/> EPO <DP n="34"/> EPO <DP n="35"/> EPO <DP n="36"/> EPO <DP n="37"/> EPO <DP n="38"/> EPO <DP n="39"/> EPO <DP n="40"/>In this sample, 5 equiv. of the amine was used.
92% With NHC-Pd(II)-Im; potassium <i>tert</i>-butylate In toluene for 4.00 h; Inert atmosphere; Reflux General procedure: Under N2 atmosphere, KOtBu (114.0 mg, 1.0 mmol), NHC-Pd(II)-Im complex 1 (5.2 mg, 1.0 mol percent), dry toluene (1.0 mL), chlorobenzene 2a (0.8 mmol), and aniline 3a (0.96 mmol) were successively added into a Schlenk reaction tube. The reaction mixture was stirred under reflux for 4 h. Then the solvent was removed under reduced pressure and the residue was purified by a flash chromatography on silica gel to give the pure product 4a.

Reference: [1] European Journal of Organic Chemistry, 2015, vol. 2015, # 9, p. 2042 - 2050
[2] Transition Metal Chemistry, 2016, vol. 41, # 5, p. 525 - 529
[3] Organometallics, 2014, vol. 33, # 7, p. 1587 - 1593
[4] RSC Advances, 2016, vol. 6, # 29, p. 24484 - 24490
[5] Journal of Organic Chemistry, 2002, vol. 67, # 16, p. 5553 - 5566
[6] European Journal of Organic Chemistry, 2012, # 21, p. 3972 - 3977
[7] Organic and Biomolecular Chemistry, 2016, vol. 14, # 8, p. 2563 - 2571
[8] Patent: CN106892945, 2017, A. Location in patent: Paragraph 0140; 0141; 0142
[9] Journal of Organometallic Chemistry, 2007, vol. 692, # 17, p. 3732 - 3742
[10] European Journal of Organic Chemistry, 2016, vol. 2016, # 10, p. 1908 - 1914
[11] Journal of Organic Chemistry, 2006, vol. 71, # 14, p. 5117 - 5125
[12] Journal of Chemical Research, 2010, # 3, p. 163 - 166
[13] Journal of Organic Chemistry, 2010, vol. 75, # 19, p. 6477 - 6488
[14] Inorganica Chimica Acta, 2012, vol. 386, p. 22 - 26
[15] Tetrahedron, 2017, vol. 73, # 52, p. 7308 - 7314
[16] Dalton Transactions, 2018, vol. 47, # 26, p. 8690 - 8696
[17] Journal of Organic Chemistry, 2006, vol. 71, # 10, p. 3928 - 3934
[18] Tetrahedron, 2008, vol. 64, # 29, p. 6920 - 6934
[19] Patent: WO2006/130842, 2006, A1. Location in patent: Page/Page column 28-29; 38
[20] Organic Letters, 2005, vol. 7, # 22, p. 4907 - 4910
[21] Tetrahedron Letters, 2004, vol. 45, # 45, p. 8319 - 8321
[22] Tetrahedron, 2012, vol. 68, # 10, p. 2414 - 2420
[23] Journal of Organometallic Chemistry, 2010, vol. 695, # 14, p. 1768 - 1775
[24] Journal of Organic Chemistry, 2002, vol. 67, # 18, p. 6479 - 6486
[25] ACS Catalysis, 2018, vol. 8, # 7, p. 6606 - 6611
[26] Journal of Organic Chemistry, 2011, vol. 76, # 19, p. 7918 - 7932
[27] Journal of Organic Chemistry, 2007, vol. 72, # 16, p. 6324 - 6327
[28] European Journal of Organic Chemistry, 2014, vol. 2014, # 10, p. 2070 - 2076
[29] Angewandte Chemie - International Edition, 2017, vol. 56, # 35, p. 10569 - 10572[30] Angew. Chem., 2017, vol. 129, # 35, p. 10705 - 10708,4
  • 5
  • [ 95-49-8 ]
  • [ 1205-39-6 ]
YieldReaction ConditionsOperation in experiment
97% With aniline; sodium t-butanolate In toluene Example 48
2-methyl-diphenylamine (Table 6, Entry 2)
According to the general procedure B, 2-chlorotoluene (65 mg, 0.51 mmol) reacted with aniline (48 mg, 0.52 mmol) using 1 mol percent of Pd(dba)2, 2 mol percent of Ph5FcP(t-Bu)2, and sodium tert-butoxide (60 mg, 0.60 mmol) in toluene at 70° C. to give the title compound (92 mg, 97percent) as an oil: 1H-NMR (300 MHz, CDCl3): δ 7.19-7.27 (m, 4H, Ar-H), 7.14 (dd, 1H, J=7.2 and 7.6 Hz), 6.97-6.88 (m, 4H), 5.36 (bs, 1H, -NH-), 2.25 (s, 3H, Ar-CH3).
13C{1H}-NMR (100 MHz, CDCl3): δ 143.86, 141.13, 130.88, 129.25, 128.19, 126.69, 121.89, 120.40, 118.65, 117.37, 17.87. GC/MS(EI): m/z 183 (M+).
Reference: [1] Patent: US6562989, 2003, B2
  • 6
  • [ 100-63-0 ]
  • [ 95-53-4 ]
  • [ 1205-39-6 ]
YieldReaction ConditionsOperation in experiment
88% at 25℃; Reaction flask was added 2-methylaniline 0.107 g (1 mmol), phenylhydrazine 0.216 g(2 mmol), CuPc 0.116 Ke (0.2 mmol), Cu (SO 4) 20.052 g (0.2 mmol) and 10 ml of aceticacid, 25 °C reaction; TLC until complete reaction was followed over; After the reaction,the crude product obtained was purified by column chromatography (petroleum ether: ethylacetate = 100: 1) to give the desired product (88percent yield)
75% With tetrabenzoporphyrinatocobalt(II); copper diacetate In acetonitrile at 0℃; for 13.00 h; General procedure: Into a 25 mL round-bottom flask, amine (2) (1 mmol), Cu(OAc)2 (0.02 g, 0.1 mmol) and acetonitrile (4 mL) were added, the mixture was stirred and cooled to 0 °C. Then, CoPc (0.057 g, 0.1 mmol) was added, the solution of arylhydrazine (1) (2 mmol) in acetonitrile (2 mL) was added successively at a rate of 0.2 mmol per hour while stirring for 13 h in air. After completion of the reaction monitored by TLC analysis (developing solvent: ethyl acetate/petroleum ether (1:8)), the mixture was filtered, concentrated, and the residue was further purified by column chromatography using ethyl acetate/petroleum ether (1:100) as eluent to afford N-aryl amine 3.
Reference: [1] Patent: CN104262167, 2016, B. Location in patent: Paragraph 0106-0109
[2] Tetrahedron, 2016, vol. 72, # 41, p. 6477 - 6483
  • 7
  • [ 108-86-1 ]
  • [ 95-53-4 ]
  • [ 1205-39-6 ]
YieldReaction ConditionsOperation in experiment
91 %Chromat. With C32H26N3PPdS; sodium t-butanolate In toluene General procedure: In a typical run, an oven-dried 10 mL round bottom flask was charged with a known mole percent of catalyst, NaOtBu (1.3 mmol), aryl amine (1.2 mmol) and aryl halide (1 mmol) with the appropriate solvent(s) (4 mL). The flask was placed in a preheated oil bath at required temp. After the specified time the flask was removed from the oil bath, water (20 mL) was added, and extraction with ether (4 × 10 mL) was done. The combined organic layers were washed with water (3 × 10 mL), dried over anhydrous Na2SO4, and filtered. Solvent was removed under vacuum. The residue was dissolved in hexane and analyzed by GC–MS.#10;
Reference: [1] Journal of Organometallic Chemistry, 2010, vol. 695, # 14, p. 1768 - 1775
[2] European Journal of Organic Chemistry, 2016, vol. 2016, # 10, p. 1908 - 1914
[3] Advanced Synthesis and Catalysis, 2014, vol. 356, # 9, p. 1967 - 1973
[4] Journal of the American Chemical Society, 2017, vol. 139, # 27, p. 9144 - 9147
[5] Journal fuer Praktische Chemie (Leipzig), 1893, vol. &lt;2&gt; 48, p. 462
[6] Journal of Organometallic Chemistry, 2012, vol. 720, p. 7 - 18,12
[7] Journal of Organometallic Chemistry, 2013, vol. 724, p. 281 - 288
  • 8
  • [ 615-37-2 ]
  • [ 62-53-3 ]
  • [ 1205-39-6 ]
YieldReaction ConditionsOperation in experiment
70% With potassium hydroxide In dimethyl sulfoxide at 120℃; for 16.00 h; Inert atmosphere To a mixture of 0.05 g catalyst and aryl iodide (1.0 mmol) in9.0 cm3 DMSO, amine (1.2 mmol) and KOH (1.5 mmol)was added and the mixture was vigorously stirred at 120 Cfor appropriate time under a dry nitrogen atmosphere. Afterthe completion of the reaction, the catalyst was filtered offand washed with water followed by acetone and dried inoven. The filtrate was extracted with ethyl acetate(3 9 20 cm3) and the combined organic layers were driedwith anhydrous Na2SO4 by vacuum. The filtrate was concentratedby vacuum and the resulting residue was purifiedby column chromatography on silica gel to provide thedesired product. All the products are known and the spectroscopicdata (FT-IR and NMR) and melting points wereconsistent with those reported in the literature [26].
63% With potassium hydroxide In dimethyl sulfoxide at 140℃; for 22.00 h; Inert atmosphere General procedure: In an oven dried 100 mL RB flask, polymer supported Cu(II)catalyst (50 mg, 0.0098 mmol), aryl halide (1 mmol), aromatic amines (1.2 mmol), KOH (1 mmol), and 10 ml DMSO were stirred under nitrogen atmosphere, at 140 °C. The reaction mixtures were collected at different time intervals and identified by GCMS and quantified by GC. After the completion of the reaction, the catalyst was filtered off and washed with water followed by acetone and dried in oven. The filtrate was extracted with ethyl acetate(3 x 20 mL) and the combined organic layers were dried with anhydrous Na2SO4 by vacuum. The filtrate was concentrated by vacuum and the resulting residue was purified by column chromatography on silica gel to provide the desired product.
62% With potassium hydroxide In dimethyl sulfoxide at 140℃; for 16.00 h; Inert atmosphere General procedure: In an oven dried 100 mL round bottom flask, Cu-grafted cat-alyst (0.05 g), aryl halide (1 mmol), aromatic amines (1.2 mmol),KOH (1 mmol), and 10 mL DMSO were stirred under nitrogen atmo-sphere, at 140C. The reaction mixtures were collected at differenttime intervals and identified by GC–MS and quantified by GC.After the completion of the reaction, the catalyst was filtered offand washed with water followed by acetone and dried in oven.The filtrate was extracted with ethyl acetate (3 × 20 mL) and thecombined organic layers were dried with anhydrous Na2SO4byvacuum. The filtrate was concentrated by vacuum and the result-ing residue was purified by column chromatography on silica gelto provide the desired product.
62% With C104H96N16O8Pd2(4+)*4NO3(1-); sodium t-butanolate In toluene at 110℃; for 18.00 h; General procedure: In a 50 mL round bottom flask, the mixture of iodobenzene (2 mmol), amine (2.4 mmol), t-BuONa (3 mmol), and 1 as catalyst (0.05 mol percent) was taken in toluene (10 mL). The reaction mixture was then heated to 110°C and continued for 12–18 h. The progress of the reaction was monitored by TLC. Upon completion of the reaction the aqueous reaction mixture was extracted with ethyl acetate, washed with brine, dried over MgSO4, concentrated, and purified by column chromatography on silica gel which afforded corresponding coupling products (yield 75–96percent).

Reference: [1] Organometallics, 2012, vol. 31, # 21, p. 7336 - 7338
[2] Applied Organometallic Chemistry, 2014, vol. 28, # 2, p. 81 - 85
[3] Monatshefte fuer Chemie, 2015, vol. 146, # 8, p. 1329 - 1334
[4] Journal of Organometallic Chemistry, 2012, vol. 696, # 26, p. 4264 - 4274
[5] Journal of Molecular Catalysis A: Chemical, 2014, vol. 387, p. 7 - 19
[6] Tetrahedron Letters, 2016, vol. 57, # 14, p. 1532 - 1536
[7] Asian Journal of Chemistry, 2015, vol. 27, # 3, p. 1075 - 1078
[8] Angewandte Chemie - International Edition, 2016, vol. 55, # 42, p. 13219 - 13223[9] Angew. Chem., 2016, vol. 128, # 42, p. 13413 - 13417,5
[10] ACS Catalysis, 2014, vol. 4, # 6, p. 1725 - 1734
  • 9
  • [ 62-53-3 ]
  • [ 529-27-1 ]
  • [ 1205-39-6 ]
YieldReaction ConditionsOperation in experiment
64% With cobalt(II) phthalocyanine; copper(II) sulfate In dichloromethane at 20℃; Aniline reaction flask was added 0.093 g (1 mmol), 2- methyl-phenylhydrazine 0.244g (2 mmol), CoPc 0.057 Ke (0.1 mmol), Cu (SO 4) 20.026 g (0.1 mmol) and 10 ml of methylene chloride, 20 °C reaction; TLC until the reaction was followed completelyfinished; the crude product after the reaction was subjected to column chromatography(petroleum ether: ethyl acetate = 100: 1) to give the target product (64percent yield).
44% With tetrabenzoporphyrinatocobalt(II); copper diacetate In acetonitrile at 0℃; for 13.00 h; General procedure: Into a 25 mL round-bottom flask, amine (2) (1 mmol), Cu(OAc)2 (0.02 g, 0.1 mmol) and acetonitrile (4 mL) were added, the mixture was stirred and cooled to 0 °C. Then, CoPc (0.057 g, 0.1 mmol) was added, the solution of arylhydrazine (1) (2 mmol) in acetonitrile (2 mL) was added successively at a rate of 0.2 mmol per hour while stirring for 13 h in air. After completion of the reaction monitored by TLC analysis (developing solvent: ethyl acetate/petroleum ether (1:8)), the mixture was filtered, concentrated, and the residue was further purified by column chromatography using ethyl acetate/petroleum ether (1:100) as eluent to afford N-aryl amine 3.
Reference: [1] Patent: CN104262167, 2016, B. Location in patent: Paragraph 0166-0169
[2] Tetrahedron, 2016, vol. 72, # 41, p. 6477 - 6483
  • 10
  • [ 31608-51-2 ]
  • [ 62-53-3 ]
  • [ 1205-39-6 ]
YieldReaction ConditionsOperation in experiment
77% With sodium acetate; palladium diacetate; triphenylphosphine In toluene at 100℃; for 12.00 h; Schlenk technique; Inert atmosphere General procedure: A Schlenk reaction tube was charged with Amine or amide 1 (1.2 mmol), aryltrimethylgermane 2 (1.0 mmol), Pd(OAc)2 (5 mol percent), PPh3 (5 mol percent), toluene (2.0 mL), under argon atmosphere at 100 °C for 12 h. After completion of the reaction, asindicated by TLC, the reaction mixture was extracted with diethyl ether (3×10 mL). The combined organic layer was washedby water and dried by Na2SO4. The solvent was removed in vacuo and the residue, further purification was carried out byshort column chromatography (silica gel 300400 mesh, petroleum ether / ethyl acetate as the eluent) to give the targetmolecules.
Reference: [1] Synlett, 2016, vol. 27, # 13, p. 1945 - 1948
  • 11
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  • [ 1205-39-6 ]
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[2] Synlett, 2011, # 7, p. 955 - 958
[3] Journal of the American Chemical Society, 2008, vol. 130, # 42, p. 13848 - 13849
  • 12
  • [ 118-90-1 ]
  • [ 62-53-3 ]
  • [ 1205-39-6 ]
YieldReaction ConditionsOperation in experiment
57% With potassium hydroxide In dimethyl sulfoxide at 130℃; for 18.00 h; The reaction was conducted at 130°C in DMSO (3mL) with substituted amine (3 mmol), substituted benzoic acid (1.3mmol), KOH (7 mmol), and 200 mL of the solution containing CuNP- or NiNP-PNF. The progress of the reaction was monitored by TLC. After reaction completion, the mixture was cooled to room temperature and was extracted with ethyl acetate (220mL). The organic extract was washed twice with water and dried with anhydrous Na2SO4, and then filtered and the solvent was evaporated to give the corresponding aryl amine. The crude product was purified by preparative TLC.
Reference: [1] Australian Journal of Chemistry, 2017, vol. 70, # 10, p. 1127 - 1137
  • 13
  • [ 591-50-4 ]
  • [ 95-53-4 ]
  • [ 1205-39-6 ]
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YieldReaction ConditionsOperation in experiment
47% With sodium acetate; palladium diacetate; triphenylphosphine In toluene at 100℃; for 12.00 h; Schlenk technique; Inert atmosphere General procedure: A Schlenk reaction tube was charged with Amine or amide 1 (1.2 mmol), aryltrimethylgermane 2 (1.0 mmol), Pd(OAc)2 (5 mol percent), PPh3 (5 mol percent), toluene (2.0 mL), under argon atmosphere at 100 °C for 12 h. After completion of the reaction, asindicated by TLC, the reaction mixture was extracted with diethyl ether (3×10 mL). The combined organic layer was washedby water and dried by Na2SO4. The solvent was removed in vacuo and the residue, further purification was carried out byshort column chromatography (silica gel 300400 mesh, petroleum ether / ethyl acetate as the eluent) to give the targetmolecules.
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