* 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 potassium hydroxide In dimethyl sulfoxide at 120℃; Inert atmosphere
General procedure: A mixture of amine (2.0 mmol), aryl halides (1.0 mmol), catalyst (1.0 molpercent Pd), and DMSO (6 ml) was stirred for 16 h under nitrogen atmosphere at 120 ◦C. The progress of reaction was monitored by gas chromatography. After completion, the reaction mixture was cooled and filtered to remove the catalyst which could be used for further reaction. The filtrate obtained was purified by flash column chromatography on silica gel to afford the desired product, which was confirmed by GC–MS. All the prepared compounds are known and compared with authentic samples.
83 %Chromat.
With C35H34N3OP2PdS(1+)*NO3(1-); sodium t-butanolate In 1,4-dioxane at 100℃; for 7 h;
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), 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 acetonitrile and analyzed by GC–MS.
Reference：
[1] Organometallics, 2012, vol. 31, # 21, p. 7336 - 7338
[2] Journal of Organic Chemistry, 2017, vol. 82, # 10, p. 5416 - 5423
[3] Journal of Molecular Catalysis A: Chemical, 2013, vol. 366, p. 321 - 332
[4] Angewandte Chemie - International Edition, 2016, vol. 55, # 42, p. 13219 - 13223[5] Angew. Chem., 2016, vol. 128, # 42, p. 13413 - 13417,5
[6] Journal of Organometallic Chemistry, 2010, vol. 695, # 21, p. 2284 - 2295
[7] Inorganica Chimica Acta, 2019, vol. 486, p. 232 - 239
2
[ 591-50-4 ]
[ 99-92-3 ]
[ 23600-83-1 ]
Yield
Reaction Conditions
Operation in experiment
53.4%
With copper; potassium carbonate In <i>N</i>-methyl-acetamide
368.1 1-(4-anilinophenyl)ethanone 4-amino-acetophenone (4.87 g; 36.0 mmol) is dissolved in dimethylformamide (75 ml). 15 g (0.108 mol) of potassium carbonate (previously dried at 170° C. under an argon atmosphere), 7.236 g (36.0 mmol) of iodobenzene, 0.4 g of copper in powder form and a catalytic quantity of copper iodide are added. The reaction mixture is taken to reflux for 12 hours. After leaving the reaction medium to return to ambient temperature, it is filtered on celite and poured into ice-cold water. After extraction with ethyl acetate, the organic phase is washed with water before being dried over magnesium sulphate, filtered and concentrated under vacuum. The product obtained is purified by crystallization from heptane in order to produce a yellow solid with a yield of 53.4percent. Melting point: 105° C.
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.
84%
With potassium phosphate; copper(l) iodide In diethylene glycol at 70℃; for 14 h; Sealed tube
General procedure: A 10 mL vial was charged with CuI (9.5 mg, 0.05 mmol), PSAP (30 mg,0.05 mmol, > 100 mesh), K3PO4 (424 mg, 2 mmol), aryl bromides (1mmol), amines (1.5 mmol), DEG (2 mL), and a magnetic stir bar. The vessel was sealed with a septum and placed into a preheated oil batchat 70 °C. The reaction mixture was held at this temperature for 14 hours. After cooling to r.t., the reaction mixture was filtered, and the precipitates were thoroughly washed with water and EtOAc (3 × 20mL). The combined organic phases were washed with water and brine, dried over anhydrous Na2SO4, and concentrated in vacuo. Theresidue was purified using flash column chromatography on silica gel(eluting with petroleum ether/EtOAc) to afford the desired products.
82%
With copper(l) iodide; tetrabutylammomium bromide; potassium hydroxide In water at 70℃; for 16 h; Green chemistry
General procedure: A 10 mL of vial was charged with CuI (10 mg, 0.05 mmol), PSP (0.25 mmol, size less than 90 μM), TBAB (40 mg, 0.25 mmol), base (1.0 mmol), aryl halides (0.5 mmol), arylamine (2.0 mmol), H2O (1.0 mL), and a magnetic stir bar. The vessel was sealed with a septum and placed into an oil bath, which was preheated to 70 °C (90 °C for alkyl amine, 120 °C for imidazole). The reaction mixture was stirred for another 16 h (8 h for imidazole). After allowing the mixture to cool to room temperature, the reaction mixture was filtrated, the precipitates were washed with water and ethyl acetate thoroughly. The filtrate was extracted with ethyl acetate (3×25 mL). The combined organic phases was washed with water and brine, dried over anhydrous Na2SO4, and concentrated in vacuo. The residue was purified by flash column chromatograph on silica gel to afford the desired products.
80%
With C21H17N3O; copper; potassium hydroxide In propan-1-ol at 80℃; for 5 h; Sealed tube
The 198 mg (1mmol) 4 - bromophenylmethyl, 279 mg (3mmol) aniline, 64 mg (1mmol) Cu, 65.4 mg (0.2mmol) ligand L6, 56mg (1mmol) KOH, 2 ml propanol, adding 10 ml reaction tube, sealing, 80 °C reaction under the condition of 5h. After the stop of the reaction, water, extracted with ethyl acetate, washing, saturated salt water washing, after drying with anhydrous sodium sulfate, filtered, the filtrate is distilled under reduced pressure, purification by silica gel chromatography separation column column, shall be 1 - (4 - (phenylamino) phenyl) b one 169 mg, yield 80percent.
75%
With C104H96N16O8Pd2(4+)*4NO3(1-); sodium t-butanolate In toluene at 110℃; for 18 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).
53%
at 90℃; for 12 h; Sealed tube
General procedure: To a 10 mL sealed vial was added Cu(OAc)2·H2O (10 mg, 0.05mmol), N-methoxy-1H-pyrrole-2-carboxamide (7 mg, 0.05 mmol), aryl bromide (1.0 mmol), amine (3.0 mmol), K3PO4 (318 mg, 1.5 mmol),PEG-100 (2.0 g) and a magnetic stir bar. The reaction mixture was stirred in an oil bath preheated to 90 °C for 12 h. After allowing the mixture to cool to room temperature, the reaction mixture was extracted with ethyl acetate (3 × 25 mL) and water (20 mL). The combined organic phases were washed with brine, dried over anhydrous Na2SO4, and concentrated in vacuo. The residue was purified by flash column chromatography on silica gel to afford the desired product.
82 %Chromat.
at 150℃; for 12 h;
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), 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 acetonitrile and analyzed by GC–MS.
Reference：
[1] Journal of Organometallic Chemistry, 2017, vol. 841, p. 57 - 61
[2] Chemical Communications, 1998, # 15, p. 1509 - 1510
[3] Applied Organometallic Chemistry, 2011, vol. 25, # 5, p. 341 - 347
[4] Synthesis (Germany), 2018, vol. 50, # 19, p. 3911 - 3920
[5] Tetrahedron, 2013, vol. 69, # 42, p. 8974 - 8977
[6] Patent: CN106883132, 2017, A, . Location in patent: Paragraph 0053-0055
[7] Applied Organometallic Chemistry, 2017, vol. 31, # 11,
[8] European Journal of Organic Chemistry, 2010, # 17, p. 3219 - 3223
[9] Tetrahedron Letters, 2016, vol. 57, # 14, p. 1532 - 1536
[10] European Journal of Organic Chemistry, 2009, # 5, p. 635 - 642
[11] Angewandte Chemie - International Edition, 2016, vol. 55, # 42, p. 13219 - 13223[12] Angew. Chem., 2016, vol. 128, # 42, p. 13413 - 13417,5
[13] Russian Chemical Bulletin, 2012, vol. 61, # 5, p. 1009 - 1013[14] Izv. Akad. Nauk, Ser. Khim., 2012, vol. 61, # 5, p. 1004 - 1008,5
[15] Synthesis (Germany), 2014, vol. 46, # 24, p. 3356 - 3364
[16] Russian Journal of General Chemistry, 2005, vol. 75, # 2, p. 207 - 211
[17] Inorganica Chimica Acta, 2019, vol. 486, p. 232 - 239
4
[ 99-91-2 ]
[ 62-53-3 ]
[ 23600-83-1 ]
Yield
Reaction Conditions
Operation in experiment
81%
With sodium t-butanolate In toluene at 100℃; for 24 h;
In a pressure tube (obtainable, for example, from Aldrich), under an argon atmosphere, 1 mmol of aryl halide, 1.2 mmol of amine, 1.4 mmol of base, a suitable amount of carbene-Pd-olefin catalyst (1 mol percent) and 100 mg of diethylene glycol di-n-butyl ether (as an internal standard for the GC analysis) were added to 5 ml of toluene. The tube was sealed and suspended in a preheated silicone oil bath. After 24 h, it was allowed to cool to room temperature. The mixture was suspended in ether, and the supernatant solution was analysed by gas chromatography. The products may be isolated by distillation or column chromatography (silica gel, hexane/ethyl acetate mixtures).
77%
With NHC-Pd(II)-Im; potassium <i>tert</i>-butylate In toluene for 8 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.
66%
With (2-mesityl-1H-inden-3-yl)dicyclohexyl phosphine; bis(dibenzylideneacetone)-palladium(0); sodium t-butanolate In 1,2-dimethoxyethane at 120℃; for 24 h; Inert atmosphere
General procedure: Pd(dba)2/1-catalyzed amination of aryl halides: An oven-dried Schlenk tube equipped with a magnetic stirring bar was charged with Pd(dba)2 (5.8 mg, 0.010 mmol), ligand 1 (8.6 mg, 0.020 mmol) and tBuONa (134 mg, 1.4 mmol). The flask was capped with a rubber septum, evacuated, and then flushed with argon. This cycle was repeated three times. Amine (1.2 mmol), aryl halide (1.0 mmol) and DME (4 mL) were then successively added by syringe. The tube was stirred at room temperature for several minutes and then placed into a preheated oil bath (120 °C) for the time period as indicated in tables. After completion of reaction as judged by GC analysis, the reaction tube was allowed to cool to room temperature and the reaction mixture was adsorbed onto silica gel, and then purified by column chromatography (hexane/ethyl acetate as eluent) to afford the desired product.
23 %Chromat.
at 150℃; for 24 h;
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), 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 acetonitrile and analyzed by GC–MS.
Reference：
[1] European Journal of Organic Chemistry, 2015, vol. 2015, # 9, p. 2042 - 2050
[2] ACS Catalysis, 2018, vol. 8, # 7, p. 6606 - 6611
[3] Journal of Organic Chemistry, 2002, vol. 67, # 18, p. 6479 - 6486
[4] Patent: US2006/122398, 2006, A1, . Location in patent: Page/Page column 9
[5] Tetrahedron, 2012, vol. 68, # 10, p. 2414 - 2420
[6] Advanced Synthesis and Catalysis, 2011, vol. 353, # 1, p. 100 - 112
[7] Organic and Biomolecular Chemistry, 2017, vol. 15, # 27, p. 5805 - 5810
[8] European Journal of Organic Chemistry, 2011, # 24, p. 4523 - 4527
[9] Journal of Organometallic Chemistry, 2012, vol. 706-707, p. 99 - 105
[10] Applied Organometallic Chemistry, 2017, vol. 31, # 11,
[11] Chemistry - A European Journal, 2007, vol. 13, # 9, p. 2701 - 2716
[12] Patent: EP1894938, 2008, A1, . Location in patent: Page/Page column 60; 61; 62; 63
[13] Inorganica Chimica Acta, 2019, vol. 486, p. 232 - 239
5
[ 591-50-4 ]
[ 12775-96-1 ]
[ 99-92-3 ]
[ 23600-83-1 ]
Yield
Reaction Conditions
Operation in experiment
53.4%
With potassium carbonate In <i>N</i>-methyl-acetamide
335.1 1-(4-anilinophenyl)ethanone 4-amino-acetophenone (4.87 g; 36.0 mmol) is dissolved in dimethylformamide (75 ml). 15 g (0.108 mol) of potassium carbonate (previously dried at 170° C. under an argon atmosphere), 7.236 g (36.0 mmol) of iodobenzene, 0.4 g of copper powder and a catalytic quantity of copper iodide are added. The reaction mixture is taken to reflux for 12 hours. After leaving the reaction medium to return to ambient temperature, the latter is filtered on celite and poured into ice-cooled water. After extraction with ethyl acetate, the organic phase is washed with water before being dried over magnesium sulphate, filtered and concentrated under vacuum. The product obtained is purified by crystallization from heptane in order to produce a yellow solid with a yield of 53.4percent. Melting point: 105° C.
Reference：
[1] Journal of the Chemical Society, 1955, p. 1278,1280
[2] Bollettino Scientifico della Facolta di Chimica Industriale di Bologna, 1959, vol. 17, p. 33,37,41
[3] Bulletin de la Societe Chimique de France, 1969, p. 2342 - 2355
25
[ 99-92-3 ]
[ 23600-83-1 ]
Reference：
[1] Journal of the Chemical Society, 1955, p. 1278,1280
[2] Bollettino Scientifico della Facolta di Chimica Industriale di Bologna, 1959, vol. 17, p. 33,37,41
26
[ 118-91-2 ]
[ 23600-83-1 ]
Reference：
[1] Bollettino Scientifico della Facolta di Chimica Industriale di Bologna, 1959, vol. 17, p. 33,37,41
With bis[chloro(1,2,3-trihapto-allylbenzene)palladium(II)]; C40H43BN2P(1-)*C16H32LiO4(1+); potassium <i>tert</i>-butylate In toluene Inert atmosphere; Schlenk technique;
4.2 General Procedure A: Palladium-Catalyzed Coupling of Aryl Bromides with Amines Using Ligand 1
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.
91%
With sodium hydroxide; water In methanol at 75℃; for 3h;
85%
With C20H26N4O4; tetrabutylammomium bromide; copper(II) oxide; potassium hydroxide In water at 130℃; for 0.0833333h; Microwave irradiation;
84%
With potassium phosphate; copper(l) iodide In diethylene glycol at 70℃; for 14h; Sealed tube;
Synthesis of 1a-s and 2a-q; General Procedure
General procedure: A 10 mL vial was charged with CuI (9.5 mg, 0.05 mmol), PSAP (30 mg,0.05 mmol, > 100 mesh), K3PO4 (424 mg, 2 mmol), aryl bromides (1mmol), amines (1.5 mmol), DEG (2 mL), and a magnetic stir bar. The vessel was sealed with a septum and placed into a preheated oil batchat 70 °C. The reaction mixture was held at this temperature for 14 hours. After cooling to r.t., the reaction mixture was filtered, and the precipitates were thoroughly washed with water and EtOAc (3 × 20mL). The combined organic phases were washed with water and brine, dried over anhydrous Na2SO4, and concentrated in vacuo. Theresidue was purified using flash column chromatography on silica gel(eluting with petroleum ether/EtOAc) to afford the desired products.
82%
With copper(l) iodide; tetrabutylammomium bromide; potassium hydroxide In water at 70℃; for 16h; Green chemistry;
2.4 General protocol for C-N coupling reaction
General procedure: A 10 mL of vial was charged with CuI (10 mg, 0.05 mmol), PSP (0.25 mmol, size less than 90 μM), TBAB (40 mg, 0.25 mmol), base (1.0 mmol), aryl halides (0.5 mmol), arylamine (2.0 mmol), H2O (1.0 mL), and a magnetic stir bar. The vessel was sealed with a septum and placed into an oil bath, which was preheated to 70 °C (90 °C for alkyl amine, 120 °C for imidazole). The reaction mixture was stirred for another 16 h (8 h for imidazole). After allowing the mixture to cool to room temperature, the reaction mixture was filtrated, the precipitates were washed with water and ethyl acetate thoroughly. The filtrate was extracted with ethyl acetate (3×25 mL). The combined organic phases was washed with water and brine, dried over anhydrous Na2SO4, and concentrated in vacuo. The residue was purified by flash column chromatograph on silica gel to afford the desired products.
81%
With palladium diacetate; caesium carbonate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl In toluene at 95℃; for 5.5h; Inert atmosphere;
17.L Step L: Synthesis of 4-phenylaminoacetophenone
0.4 g (2.01 mmol) 4-bromoacetophenone, 0.37 g (4.02 mmol) aniline, 0.02 g (0.08 mmol) palladium acetate, 0.08 g (0.12 mmol) BINAP and 0.98 g (3.02 mmol) cesium carbonate were placed in a 100 mL trinecked bottle and dissolved with 25 mL toluene. Nitrogen protection, heating to 95 °C stirring for 5.5 h. To cool the reaction liquid to room temperature, the insoluble substances are filtered out. After the filtrate was concentrated under reduced pressure, the petroleum ether: ethyl acetate (V/V) = 2:1 was used as the eluent silica gel column chromatography, and the pale yellow solid was separated to obtain 0.35g, and the yield was 81%.
80%
With C21H17N3O; copper; potassium hydroxide In propan-1-ol at 80℃; for 5h; Sealed tube;
6 Synthesis of 1- (4- (phenylamino) phenyl) ethanone
The 198 mg (1mmol) 4 - bromophenylmethyl, 279 mg (3mmol) aniline, 64 mg (1mmol) Cu, 65.4 mg (0.2mmol) ligand L6, 56mg (1mmol) KOH, 2 ml propanol, adding 10 ml reaction tube, sealing, 80 °C reaction under the condition of 5h. After the stop of the reaction, water, extracted with ethyl acetate, washing, saturated salt water washing, after drying with anhydrous sodium sulfate, filtered, the filtrate is distilled under reduced pressure, purification by silica gel chromatography separation column column, shall be 1 - (4 - (phenylamino) phenyl) b one 169 mg, yield 80%.
78%
With copper; caesium carbonate; methyl-alpha-D-glucopyranoside In water; dimethyl sulfoxide at 110℃; for 24h; Sealed tube; Green chemistry;
General Procedure
General procedure: All the reactions were carried out in DMSO-H 2 O (1:1, 2 mL) in asealed vessel. To a 10 mL hydrothermal synthesis reactor was chargedCu powder (6 mg, 0.1 mmol), MG (39 mg, 0.2 mmol), Cs 2 CO 3 (980 mg,3.0 mmol), nitrogen-containing heterocycle (1.5 mmol), amine (3.0mmol), and aryl halide (0.8 mmol). The reaction mixture was stirredfor a specified time at 100-110 °C. After TLC analysis confirmed thecomplete consumption of aryl halides, the mixture was cooled to r.t.(the pH was adjusted if the product was acidic), diluted with EtOAc(10 mL), filtered through a Celite pad, and washed with EtOAc (20-30mL). The organic layer was dried and concentrated. The residue waspurified by silica gel column chromatography to give the product.
76%
With potassium hydroxide In water at 20℃; for 6h; Green chemistry;
75%
With copper(l) iodide; N′-phenyl-1H-pyrrole-2-carbohydrazide; tetrabutylammomium bromide; potassium hydroxide In water at 20 - 130℃; Microwave irradiation;
75%
With C104H96N16O8Pd2(4+)*4NO3(1-); sodium t-butanolate In toluene at 110℃; for 18h;
Experimental procedure for Buchwald-Hartwig coupling reaction
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 %) 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 75-96%).
72%
With potassium hydroxide In N,N-dimethyl-formamide at 130℃; for 0.4h;
66%
With oxalic acid hydrazide; potassium hydroxide; tetrabutylammomium bromide; 2,5-hexadione; copper(II) oxide In water at 25 - 120℃; for 0.1h; Microwave irradiation;
58%
With (1,2-dimethoxyethane)dichloronickel(II); Ir[dF(CF3)ppy]2(dtbbpy)PF6; triethylamine; 4,4'-di-tert-butyl-2,2'-bipyridine In acetonitrile at 23 - 25℃; for 24h; Sealed tube; Irradiation; chemoselective reaction;
57%
With N'-phenyloxalyl bishydrazide; tetrabutylammomium bromide; copper(II) acetate monohydrate; 2,5-hexadione; potassium hydroxide In water at 100℃; Inert atmosphere; Sealed tube;
53%
With N-methoxy-1H-pyrrole-2-carboxamide; potassium phosphate; copper(II) acetate monohydrate at 90℃; for 12h; Sealed tube;
General Procedure A for synthesis of compounds 3a-3k, 4a-4x:
General procedure: To a 10 mL sealed vial was added Cu(OAc)2·H2O (10 mg, 0.05mmol), N-methoxy-1H-pyrrole-2-carboxamide (7 mg, 0.05 mmol), aryl bromide (1.0 mmol), amine (3.0 mmol), K3PO4 (318 mg, 1.5 mmol),PEG-100 (2.0 g) and a magnetic stir bar. The reaction mixture was stirred in an oil bath preheated to 90 °C for 12 h. After allowing the mixture to cool to room temperature, the reaction mixture was extracted with ethyl acetate (3 × 25 mL) and water (20 mL). The combined organic phases were washed with brine, dried over anhydrous Na2SO4, and concentrated in vacuo. The residue was purified by flash column chromatography on silica gel to afford the desired product.
87.9 % Chromat.
With [2,2'-bis(dicyclohexylphosphino)diphenyl oxide]*PdCl2; sodium t-butanolate In toluene at 85℃; for 2h;
82 %Chromat.
With C35H34N3OP2PdS(1+)*NO3(1-); sodium t-butanolate at 150℃; for 12h;
2.5.2. General procedure for Buchwald-type C-N coupling reactions
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), 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 acetonitrile and analyzed by GC-MS.
>99 %Chromat.
With 4-methyl-pent-3-en-2-one; [(DTBNpP)PdCl2]2; sodium t-butanolate In toluene at 22℃; for 15h; Inert atmosphere; Sealed tube;
88 %
With C36H48Cl2NOPPd; sodium t-butanolate In tetrahydrofuran at 25℃; Inert atmosphere; Schlenk technique;
With potassium hexafluoridophosphate; ferrocenium hexafluorophosphate; copper(II) acetate dihydrate; anhydrous Sodium acetate; triethylamine In acetonitrile at 40℃; Inert atmosphere; Electrochemical reaction;
65%
With 2,6-dimethylpyridine; tetra-n-butylammonium perchlorate; copper (II) acetate; triethylamine In acetonitrile at 20℃; for 20h; Electrochemical reaction; chemoselective reaction;
47%
With 2,6-dimethylpyridine; fac-tris(2-phenylpyridinato-C<SUP>2</SUP>,N)iridium(III); copper (II) acetate; n-tetradecanoic acid In toluene; acetonitrile at 35℃; for 20h; Irradiation;
18%
With anhydrous Sodium acetate; copper atom In methanol at 40℃; for 12h; Milling; chemoselective reaction;
4.3 General procedure for cross-coupling of amines
General procedure: To a stainless steel milling jar (25 or 50mL) equipped with 8-12 stainless steel milling balls (7.0-10.0mm in diameter) were added amine (4, 1.5mmol, 1.5equiv.), arylboronic acid (2, 1.0mmol, 1.0equiv.), copper powders (99.9% metal basis, <425μm) (6.5mg, 0.10mmol, 0.1equiv.), NaOAc (41mg, 0.5equiv.) and 1.0mL MeOH. Then, the milling jar was clamped into planetary ball mill, heated to 40°C and milled at 600rpm for given time. The operation cycle was 60min on, 5min off to supply air and take sample for TLC (∼55°C at the end). After the elapsed time, the reaction mixture was transferred from the milling jar into a flask with aid of CH2Cl2 (3×5mL) and filtered over a small pad of Celite (2cm height). The filtrate was concentrated by rotavapor to afford the crude product, which was purified by flash column chromatography on silica gel using a gradient of ethyl acetate in petroleum ether. For characterization of products see supplementary materials.
With 2,6-dimethylpyridine; n-tetradecanoic acid In toluene at 20℃;
With dichloro(3-chloropyridinyl)(1,3-(diisopropylphenyl)-4,5-bis(dimethylamino)imidazol-2-ylidene)palladium(II); caesium carbonate In 1,2-dimethoxyethane at 80℃; for 24h; Schlenk technique; Sealed tube; Inert atmosphere;
90%
With sodium t-butanolate In tetrahydrofuran at 60℃; for 18h;
87%
With potassium hydroxide; bis(tri-tert-butylphosphine)palladium(0); cetyltrimethylammonim bromide In water; toluene at 90℃; for 2h;
81%
With sodium t-butanolate In toluene at 100℃; for 24h;
55
In a pressure tube (obtainable, for example, from Aldrich), under an argon atmosphere, 1 mmol of aryl halide, 1.2 mmol of amine, 1.4 mmol of base, a suitable amount of carbene-Pd-olefin catalyst (1 mol %) and 100 mg of diethylene glycol di-n-butyl ether (as an internal standard for the GC analysis) were added to 5 ml of toluene. The tube was sealed and suspended in a preheated silicone oil bath. After 24 h, it was allowed to cool to room temperature. The mixture was suspended in ether, and the supernatant solution was analysed by gas chromatography. The products may be isolated by distillation or column chromatography (silica gel, hexane/ethyl acetate mixtures).
77%
With NHC-Pd(II)-Im; potassium <i>tert</i>-butylate In toluene for 8h; Inert atmosphere; Reflux;
4.2. Experimental procedures
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.
74%
Stage #1: para-chloroacetophenone With 2,6-diisopropoxyphenyl(dicyclohexyl)phosphonium tetrafluoroborate; palladium diacetate; potassium hydroxide In toluene at 20℃; for 0.0666667h; Inert atmosphere;
Stage #2: aniline In toluene at 110℃; for 4h; Inert atmosphere;
74%
With C29H37O2P; bis(dibenzylideneacetone)-palladium(0); sodium t-butanolate In water at 110℃; for 24h; Sealed tube; Inert atmosphere;
66%
With oxalic acid hydrazide; phosphoric acid trihydrate; tetrabutylammomium bromide; 2,5-hexanedione; copper(II) oxide In water at 120℃; for 24h;
66%
With (2-mesityl-1H-inden-3-yl)dicyclohexyl phosphine; bis(dibenzylideneacetone)-palladium(0); sodium t-butanolate In 1,2-dimethoxyethane at 120℃; for 24h; Inert atmosphere;
4.5. General procedures for palladium-catalyzed amination of aryl halides
General procedure: Pd(dba)2/1-catalyzed amination of aryl halides: An oven-dried Schlenk tube equipped with a magnetic stirring bar was charged with Pd(dba)2 (5.8 mg, 0.010 mmol), ligand 1 (8.6 mg, 0.020 mmol) and tBuONa (134 mg, 1.4 mmol). The flask was capped with a rubber septum, evacuated, and then flushed with argon. This cycle was repeated three times. Amine (1.2 mmol), aryl halide (1.0 mmol) and DME (4 mL) were then successively added by syringe. The tube was stirred at room temperature for several minutes and then placed into a preheated oil bath (120 °C) for the time period as indicated in tables. After completion of reaction as judged by GC analysis, the reaction tube was allowed to cool to room temperature and the reaction mixture was adsorbed onto silica gel, and then purified by column chromatography (hexane/ethyl acetate as eluent) to afford the desired product.
49%
With potassium hydroxide In water at 20℃; for 6h; Green chemistry;
With sodium t-butanolate In toluene at 120℃; for 12h;
With sodium t-butanolate In toluene at 120℃; for 12h;
B.III.8
III. Buchwald-Hartwig amination of aryl halides 5 ml dry toluene, 5 mmol aryl halide, 6 mmol amine and 6 mmol NaOtBu were placed in a Schlenk tube. Next the catalyst Na2PdCl4 / EtFluPCy2 (9) (as phosphonium salt (9a)) (1:2) was added in the given concentration. The reaction mixture was stirred at 120°C in an aluminum block. After cooling to room temperature the reaction mixture was diluted with ether (15 ml), washed with water (10 ml), the organic phase dried over MgSO4, filtered and concentrated in vacuo. The product was isolated by column chromatography (silica, cyclohexane /ethylacetate (90:10). Alternatively the yield was determined via gaschromatography with hexadecane or diethylene glycol di-n-butylether as an internal standard.
23 %Chromat.
With C35H34N3OP2PdS(1+)*NO3(1-); sodium t-butanolate at 150℃; for 24h;
2.5.2. General procedure for Buchwald-type C-N coupling reactions
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), 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 acetonitrile and analyzed by GC-MS.
With triethylamine In N,N-dimethyl-formamide at 60℃; for 2h;
General procedure for Chan-Lam coupling
General procedure: In a 50 cm3 round-bottom flask, phenylboronic acid(1.2 mmol), primary amine (1.0 mmol), triethyl amine(2.0 mmol), and 80 mg (0.018 mol% of Cu) Cu-ACP-Am-Fe3O4SiO2 were mixed in 5 cm3 DMF and the reactionwas allowed to stir at 60 °C temperature for 2 h in aerobiccondition. Reactions was monitored by thin-layer chromatography(TLC) using aluminum-backed silica gel 60 (F254)plates. After completion of the reaction, the catalyst wasseparated magnetically using bar magnet. Finally, the resultingsolution was extracted with ethyl acetate and dried overanhydrous Na2SO4.The solvent was removed under reducedpressure and the product was purified by silica gel columnchromatography.
83%
With copper immobilized at polyimide covalent organic framework In methanol; lithium hydroxide monohydrate at 20℃; for 8h;
64%
With pyridine; 4 A molecular sieve; copper (II) acetate In dichloromethane at 20℃; for 72h;
33%
With anhydrous Sodium acetate; copper atom In methanol at 40℃; for 6h; Milling; chemoselective reaction;
4.3 General procedure for cross-coupling of amines
General procedure: To a stainless steel milling jar (25 or 50mL) equipped with 8-12 stainless steel milling balls (7.0-10.0mm in diameter) were added amine (4, 1.5mmol, 1.5equiv.), arylboronic acid (2, 1.0mmol, 1.0equiv.), copper powders (99.9% metal basis, <425μm) (6.5mg, 0.10mmol, 0.1equiv.), NaOAc (41mg, 0.5equiv.) and 1.0mL MeOH. Then, the milling jar was clamped into planetary ball mill, heated to 40°C and milled at 600rpm for given time. The operation cycle was 60min on, 5min off to supply air and take sample for TLC (∼55°C at the end). After the elapsed time, the reaction mixture was transferred from the milling jar into a flask with aid of CH2Cl2 (3×5mL) and filtered over a small pad of Celite (2cm height). The filtrate was concentrated by rotavapor to afford the crude product, which was purified by flash column chromatography on silica gel using a gradient of ethyl acetate in petroleum ether. For characterization of products see supplementary materials.
With pyridine; copper(ll) acetate In dichloromethane at 20℃;
With [1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene](3chloro-pyridyl)palladium(II) dichloride; caesium carbonate In 1,2-dimethoxyethane at 80℃; for 24h; Inert atmosphere;
89%
With dichloro(1,3-bis(2,6-bis(3-pentyl)phenyl)imidazolin-2-ylidene)(3-chloropyridyl)palladium(II); 2,2,5,7,8-pentamethylchroman-6-ol potassium salt In 1,2-dimethoxyethane at 80℃; for 4h; Inert atmosphere;
32%
With [1,1′-bis(diphenylphosphino)ferrocene]bis(triphenylphosphite)nickel(0); 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; sodium t-butanolate In toluene at 100℃; for 18h; Schlenk technique; Inert atmosphere;
25%
With potassium hydroxide In 1,4-dioxane at 100℃; for 16h;
With potassium carbonate In <i>N</i>-methyl-acetamide
335.1 335.1
335.1 1-(4-anilinophenyl)ethanone 4-amino-acetophenone (4.87 g; 36.0 mmol) is dissolved in dimethylformamide (75 ml). 15 g (0.108 mol) of potassium carbonate (previously dried at 170° C. under an argon atmosphere), 7.236 g (36.0 mmol) of iodobenzene, 0.4 g of copper powder and a catalytic quantity of copper iodide are added. The reaction mixture is taken to reflux for 12 hours. After leaving the reaction medium to return to ambient temperature, the latter is filtered on celite and poured into ice-cooled water. After extraction with ethyl acetate, the organic phase is washed with water before being dried over magnesium sulphate, filtered and concentrated under vacuum. The product obtained is purified by crystallization from heptane in order to produce a yellow solid with a yield of 53.4%. Melting point: 105° C.
With C29H25CuIN3OPPd; sodium t-butanolate In toluene at 40℃; for 24h;
53.4%
With copper; potassium carbonate In <i>N</i>-methyl-acetamide
368.1 368.1
368.1 1-(4-anilinophenyl)ethanone 4-amino-acetophenone (4.87 g; 36.0 mmol) is dissolved in dimethylformamide (75 ml). 15 g (0.108 mol) of potassium carbonate (previously dried at 170° C. under an argon atmosphere), 7.236 g (36.0 mmol) of iodobenzene, 0.4 g of copper in powder form and a catalytic quantity of copper iodide are added. The reaction mixture is taken to reflux for 12 hours. After leaving the reaction medium to return to ambient temperature, it is filtered on celite and poured into ice-cold water. After extraction with ethyl acetate, the organic phase is washed with water before being dried over magnesium sulphate, filtered and concentrated under vacuum. The product obtained is purified by crystallization from heptane in order to produce a yellow solid with a yield of 53.4%. Melting point: 105° C.
24%
With copper; potassium carbonate In N,N-dimethyl-formamide at 20 - 120℃; for 16h;
63.1 Step-1: Synthesis of 1-(4-(phenylamino)phenyl)ethanone
To a stirred solution of 1-(4-aminophenyl)ethanone (1.2 g, 5.88 mmol, 1.0 eq.) and iodobenzene (0.79 g, 5.88 mmol, 1.0 eq.) in DMF (15 mL) was added K2CO3 (2.43 g, 17.64 mmol, 3.0 eq.), Cu powder (0.1 g) and CuI (0.011 g, 0.058 mmol, 0.01 eq.) at RT. The resulting mixture heated at 120° C. for 16 h. Following this, reaction was allowed to cool to RT and filtered through celite pad, the celite pad washed with ethyl acetate and water. The aqueous layer was separated extracted using ethyl acetate (3*20 mL). The combined organic layers were washed with brine (30 mL), dried over anhydrous Na2SO4, filtered and concentrated under vacuum to get the solid residue which purified by flash column to get title compound (0.3 g, 24%). LCMS: 212.1 [M+1]+; 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 7.87 (m, J=8.77 Hz, 2H) 7.34 (d, J=7.89 Hz, 2H) 7.19 (d, J=7.45 Hz, 2H) 6.99 (m, J=8.77 Hz, 2H) 2.53 (s, 3H).
With C29H25CuIN3OPPd; sodium t-butanolate In toluene at 40℃; for 24h;
85%
With potassium phosphate; copper(l) iodide; N',N'-diphenyl-1H-pyrrole-2-carbohydrazide In diethylene glycol at 20℃; Sealed tube;
85%
With silver hexafluoroantimonate; 2,6-di-tert-butyl-pyridine; (MeDalphos)AuCl In methanol at 0 - 80℃; for 16h; Inert atmosphere;
76%
With potassium hydroxide In dimethyl sulfoxide at 120℃; Inert atmosphere;
General experimental procedure for amination reaction
General procedure: A mixture of amine (2.0 mmol), aryl halides (1.0 mmol), catalyst (1.0 mol% Pd), and DMSO (6 ml) was stirred for 16 h under nitrogen atmosphere at 120 ◦C. The progress of reaction was monitored by gas chromatography. After completion, the reaction mixture was cooled and filtered to remove the catalyst which could be used for further reaction. The filtrate obtained was purified by flash column chromatography on silica gel to afford the desired product, which was confirmed by GC-MS. All the prepared compounds are known and compared with authentic samples.
76%
With (1,2-dimethoxyethane)dichloronickel(II); Ir[dF(CF3)ppy]2(dtbbpy)PF6; triethylamine; 4,4'-di-tert-butyl-2,2'-bipyridine In acetonitrile at 23 - 25℃; for 24h; Sealed tube; Irradiation; chemoselective reaction;
61%
With NiCl2dtbbpy; [Ir(df(CF3)ppy)2(dtbbpy)]PF6; triethylamine In acetonitrile at 20℃; Glovebox; Sealed tube; Irradiation;
83 %Chromat.
With potassium <i>tert</i>-butylate In toluene at 120℃; for 24h; Inert atmosphere;
83 %Chromat.
With C35H34N3OP2PdS(1+)*NO3(1-); sodium t-butanolate In 1,4-dioxane at 100℃; for 7h;
2.5.2. General procedure for Buchwald-type C-N coupling reactions
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), 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 acetonitrile and analyzed by GC-MS.
81 %
With 1,8-diazabicyclo[5.4.0]undec-7-ene; 4,4'-di-tert-butyl-2,2'-bipyridine; nickel dichloride In tetrahydrofuran at 30℃; Inert atmosphere; Glovebox; Schlenk technique; Sealed tube; UV-irradiation;
With palladium diacetate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene In 1-methyl-pyrrolidin-2-one at 150℃; for 24h; Inert atmosphere; Sealed vessel;
Stage #1: iodobenzene With potassium phosphate; copper(l) iodide; lithium amide In N,N-dimethyl-formamide at 130℃; for 6h; Inert atmosphere;
Stage #2: 4-Iodoacetophenone In N,N-dimethyl-formamide at 130℃; for 18h; Inert atmosphere; chemoselective reaction;
Stage #1: p-aminobenzophenone With n-butyllithium; dichloro(N,N,N’,N‘-tetramethylethylenediamine)zinc In tetrahydrofuran; hexane at 0 - 20℃; for 0.5h; Inert atmosphere; Schlenk technique;
Stage #2: phenylmagnesium bromide With 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; bis(acetylacetonate)nickel(II); 1,2-dichloro-2-methylpropane In tetrahydrofuran; hexane at 0 - 20℃; for 3h; Inert atmosphere; Schlenk technique;
Stage #1: p-aminobenzophenone With copper diacetate In acetonitrile at -5℃; for 0.25h;
Stage #2: With 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione In acetonitrile at -5℃; for 0.0833333h;
Stage #3: phenylhydrazine In acetonitrile at -5℃; for 3.33333h;
Stage #1: 1-(4-nitrophenyl)ethan-1-one With [2,2]bipyridinyl; MoO<SUB>2</SUB>Cl<SUB>2</SUB>(DMF)<SUB>2</SUB> In toluene for 0.0333333h;
Stage #2: phenylboronic acid With triphenylphosphine In toluene at 100℃; for 19h;
78%
With tungsten hexacarbonyl; triphenylphosphine at 22℃; for 24h; Inert atmosphere; Schlenk technique; Sealed tube; Irradiation;
With potassium phosphate; bis(tri-tert-butylphosphine)palladium(0); copper(I) bromide In acetonitrile at 60℃; for 16h; Inert atmosphere; Glovebox; Sealed tube;
With ammonium acetate; sodium cyanoborohydride In ethanol at 20 - 50℃; for 16h;
63.2 Step-2: Synthesis of 4-(1-aminoethyl)-N-phenylaniline
To a stirred solution of 1-(4-(phenylamino)phenyl)ethanone (0.2 g, 0.94 mmol, 1.0 eq.) and Ammonium acetate (0.72 g, 9.4 mmol, 10.0 eq.) in EtOH (10 mL) was added sodium cyanoborohydride (0.05 g, 0.94 mmol, 1.0 eq.) at RT. The resulting mixture was heated at 50° C. for 16 h. Following this, the reaction mixture was allowed to cool to RT, basified with 6N NaOH until pH10 and extracted with EtOAc (3×15 mL). The combined organic layers were washed with brine (25 mL), dried over Na2SO4 and concentrated under reduced pressure to get the desired product which was carried forward without any further purification (0.18 g 90%). LCMS: 213.3 [M+1]+
With copper(II) acetate monohydrate; potassium carbonate at 110℃; for 12h; Inert atmosphere;
Synthesis of 4a-p; General Procedure B
General procedure: To a solution of aromatic amine (1.53 mmol), Cu(OAc)2·H2O (0.13 mmol), K2CO3(3.84 mmol) in DEG (3 mL) were added aryl halides (1.28 mmol). The flask wasevacuated and backfilled with argon (3×), and the resulting mixture was heated in an oilbath with appropriate temperature under rapid stirring for the indicated time. After thecomplete consumption of aryl halide as monitored by TLC, the flask was cooled to r.t.The flask was opened to air, and the reaction mixture (if the product was acidic, themixture was acidified) was extracted with ethyl acetate (3×10 mL), and the organiclayer was washed with water (2×10 mL) and once with brine (10 mL), dried withmagnesium sulfate and concentrated in vacuo. The product was purified by columnchromatography on silica gel.
3. General Procedure for the Synthesis of C-N coupling products
General procedure: 0.23 g (1.20 mmol) of 1a and 0.13 g (1.44 mmol) of 2h were added to 5mL ClCH2CH2Cl. The mixture was stirred for 2 h at room temperature. The reaction was monitored by TLC. After the reaction was completed, the mixture was concentrated under vacuum and then purified by flash chromatography to afford compound 3h.
With bis(1,5-cyclooctadiene)nickel (0); 3,4-bis(dicyclohexylphosphino)thiophene In toluene at 150℃; for 24h; Sealed tube;
General procedure for the Buchwald-Hartwig amination employing solidamines
General procedure: An oven-dried vial was charged with the corresponding carbamate(0.5 mmol, 1.0 eq.), the corresponding amine (0.5 mmol, 1.0 eq.), Ni(cod)2 (5 mol%)and dcypt (10 mol%). Thereafter PhMe (2.5 ml) was added and the vial was sealed.The reaction mixture was stirred at 150 °C for 24 h. After that the reaction wasallowed to cool to room temperature and opened to air. The volatiles were removedunder reduced pressure, and purification via flash column chromatographyafforded the title compounds.
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