* 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.
With bis-triphenylphosphine-palladium(II) chloride; triphenylphosphine; sodium t-butanolate In o-xylene for 12 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.
Reference：
[1] Journal of Organic Chemistry, 2013, vol. 78, # 10, p. 4649 - 4664
[2] RSC Advances, 2013, vol. 3, # 12, p. 3840 - 3843
[3] Tetrahedron, 2014, vol. 70, # 32, p. 4754 - 4759
2
[ 6781-98-2 ]
[ 87-62-7 ]
[ 74443-35-9 ]
Yield
Reaction Conditions
Operation in experiment
99%
With NHC-Pd(II)-Im; potassium <i>tert</i>-butylate In toluene for 4 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.
99%
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 3 h;
The Protection of Nitrogen Under, The Reaction Tube to are potassium tertiary Butanol (0.91 mmol) and. 1,. 4 - dioxane (0.5 ml), [Pd (of IPr) (isoquinoline) CI2] Complex (41 is) of The Solution (10 L, (0.84 mmol), 2, 6 - dimethyl chlorobenzene (0.7 mmol), the mixture (2), 2 - 6 - dimethyl - chlorobenzene (0.7 mmol) Is available in 110 ° C ° C stirring for 3 hours, stopping the reaction, cooling to room temperature, pressure reduced on on lathe does solvent, rapid column chromatography separation to obtain the product, yield is 99percent. White solid.
Reference：
[1] Journal of Organometallic Chemistry, 2007, vol. 692, # 17, p. 3732 - 3742
[2] Advanced Synthesis and Catalysis, 2011, vol. 353, # 4, p. 533 - 537
[3] Tetrahedron, 2012, vol. 68, # 10, p. 2414 - 2420
[4] Organometallics, 2012, vol. 31, # 8, p. 3402 - 3409
[5] Organic and Biomolecular Chemistry, 2016, vol. 14, # 8, p. 2563 - 2571
[6] Patent: CN106892945, 2017, A, . Location in patent: Paragraph 0124; 0141; 0142; 0143; 0144; 0145; 0146
[7] Journal of Organic Chemistry, 2008, vol. 73, # 8, p. 3047 - 3062
[8] Organometallics, 2011, vol. 30, # 16, p. 4432 - 4436
[9] RSC Advances, 2013, vol. 3, # 12, p. 3840 - 3843
[10] RSC Advances, 2016, vol. 6, # 29, p. 24484 - 24490
[11] Chemistry - A European Journal, 2013, vol. 19, # 51, p. 17358 - 17368
[12] ChemCatChem, 2015, vol. 7, # 24, p. 4021 - 4024
[13] Journal of Organic Chemistry, 2004, vol. 69, # 26, p. 9135 - 9142
[14] Journal of Organic Chemistry, 2013, vol. 78, # 10, p. 4649 - 4664
[15] Journal of Organic Chemistry, 2018, vol. 83, # 16, p. 9144 - 9155
[16] Advanced Synthesis and Catalysis, 2012, vol. 354, # 10, p. 1897 - 1901
[17] Organometallics, 2012, vol. 31, # 19, p. 6947 - 6951
[18] Journal of the American Chemical Society, 2006, vol. 128, # 12, p. 4101 - 4111
[19] Synlett, 2005, # 2, p. 275 - 278
[20] Inorganica Chimica Acta, 2012, vol. 386, p. 22 - 26
[21] Organic Letters, 2011, vol. 13, # 20, p. 5540 - 5543
[22] Journal of Organic Chemistry, 2017, vol. 82, # 6, p. 2914 - 2925
[23] Angewandte Chemie - International Edition, 2014, vol. 53, # 25, p. 6482 - 6486[24] Angew. Chem., 2014, vol. 126, # 25, p. 6600 - 6604,5
[25] Organometallics, 2013, vol. 32, # 1, p. 330 - 339
3
[ 576-22-7 ]
[ 74443-35-9 ]
[ 87-62-7 ]
Reference：
[1] Journal of the American Chemical Society, 1998, vol. 120, # 30, p. 7651 - 7652
With NHC-Pd(II)-Im; potassium tert-butylate; In toluene; for 4h;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 %), 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.
99%
With [1,3-bis(2,6-diisopropylphenyl)imidazol-2-yl-isoquinolin-2-yl]palladium dichloride; potassium tert-butylate; In 1,4-dioxane; at 110℃; for 3h;
The Protection of Nitrogen Under, The Reaction Tube to are potassium tertiary Butanol (0.91 mmol) and. 1,. 4 - dioxane (0.5 ml), [Pd (of IPr) (isoquinoline) CI2] Complex (41 is) of The Solution (10 L, (0.84 mmol), 2, 6 - dimethyl chlorobenzene (0.7 mmol), the mixture (2), 2 - 6 - dimethyl - chlorobenzene (0.7 mmol) Is available in 110 C C stirring for 3 hours, stopping the reaction, cooling to room temperature, pressure reduced on on lathe does solvent, rapid column chromatography separation to obtain the product, yield is 99%. White solid.
97%
With C40H44ClN3Pd; potassium tert-butylate; In toluene; at 110℃; for 24h;Inert atmosphere;
General procedure: Under N2 atmosphere, KOtBu (1.3 equiv), toluene (1.0 mL), amines 5 (0.84 mmol), aryl chlorides 4 (0.7 mmol) and finally a solution of complex 3a (20-100muL, 0.01-0.05 mol%, prepared from 0.014 mmol 3a in 4.0mL toluene) were successively added into a Schlenk reaction tube. The mixture was stirred vigorously at 110 C for 24h. Then the solvent was removed under reduced pressure and the residue was purified by flash column chromatography (SiO2) to give the corresponding products.
With bis-triphenylphosphine-palladium(II) chloride; triphenylphosphine; sodium t-butanolate; In o-xylene; for 12h;Inert atmosphere; Reflux; Schlenk technique;
General procedure: In a Schlenk tube with a magnetic bar, base (3.0mmol), PdCl2(Ph3P)2 (3.5mg, 0.5mol%)and Ph3P (2.6mg, 1.0mol%), 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.
With palladium diacetate; sodium t-butanolate; tri tert-butylphosphoniumtetrafluoroborate; In toluene; for 6h;Inert atmosphere; Reflux;
Add B29-B (3.8g, 0.010mol) to a 500mL three-necked flask,Carbazole (3.7 g, 0.022 mol),Sodium tert-butoxide (3.0 g, 0.030 mol) and toluene (60 mL) under a nitrogen atmospherePalladium acetate (22 mg, 0.0001 mol) and tri-tert-butylphosphonium tetrafluoroborate (58 mg, 0.0002 mol) were added.After heating to reflux, the reaction was kept for 6.0 hrs, and the reaction was completed by TLC.Decrease to 20 ~ 25 C, add water (10mL) to quench the reaction, stratify, the organic phase is desolvent under reduced pressure to no fraction,That is, B29 crude. Further recrystallization using an ethyl acetate/ethanol mixed solvent, suction filtration, and collecting the filter cake.Obtained B29 of 5.3g, and the calculated yield was69.55%,
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