2,4-Dimethy diiphenylamine

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.General procedure: I n this Example, an aryl fluorosulfonate is reacted with aniline as shown in Equation 7: Equation 7 [0051] The present Example is performed in a nitrogen- filled glovebox. To each of 12 30 mL vials are added one of the aryl fluorosulfonates selected from Table 1 where R in Equation 7 represents one or more groups joined to the aryl ring as shown (2.50 mmol), Xantphos (0.017 g; 0.03 mmol); potassium carbonate (0.691 g; 5.00 mmol), and 1, 4-dioxane (5 mL). To each stirring mixture is added aniline (274 uL) and CpPd (cinnamyl) (0.007 g in 100 uL 1, 4-dioxane). Each reaction mixture is heated at 80 °C for 12 to 24 hours. The reaction mixture is cooled to room temperature and adsorbed onto silica gel. The product is purified by flash chromatography (ISCO, manufactured by Teledyne) and the volatiles are removed by vacuum to reveal the desired product having yields recorded in Table 1.General procedure: An Omnifit glass column (6.6×150mm) was filled with copper powder (5.5cm height) and connected to a 10mL stainless steel reactor coil and both were heated to 100°C using a Vapourtec R4 reactor module. Using a Vapourtec R2C+ flow chemistry system, a 2mL solution containing arylboronic acid (0.8mmol) and amine (2.4mmol) in acetonitrile was placed in 2mL sample loop A and 2mL solution containing TEMPO (1.2mmol) and acetic acid (1.6mmol) in acetonitrile was placed in 2mL sample loop B. The reactants were progressed through the copper column and SS coil reactor (0.30mL/min), with each sample loop/pump set at 0.15mL/min, and a 250psi back-pressure regulator and collected in a 100mL RB flask. The solvent removed and product purified with a Teledyne Combiflash Rf and silica gel column chromatography in ethyl acetate:hexane (typically 1:19) to yield an isolated product.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.General procedure: I n this Example, an aryl fluorosulfonate is reacted with aniline as shown in Equation 7: Equation 7 [0051] The present Example is performed in a nitrogen- filled glovebox. To each of 12 30 mL vials are added one of the aryl fluorosulfonates selected from Table 1 where R in Equation 7 represents one or more groups joined to the aryl ring as shown (2.50 mmol), Xantphos (0.017 g; 0.03 mmol); potassium carbonate (0.691 g; 5.00 mmol), and 1, 4-dioxane (5 mL). To each stirring mixture is added aniline (274 uL) and CpPd (cinnamyl) (0.007 g in 100 uL 1, 4-dioxane). Each reaction mixture is heated at 80 °C for 12 to 24 hours. The reaction mixture is cooled to room temperature and adsorbed onto silica gel. The product is purified by flash chromatography (ISCO, manufactured by Teledyne) and the volatiles are removed by vacuum to reveal the desired product having yields recorded in Table 1.General procedure: An Omnifit glass column (6.6×150mm) was filled with copper powder (5.5cm height) and connected to a 10mL stainless steel reactor coil and both were heated to 100°C using a Vapourtec R4 reactor module. Using a Vapourtec R2C+ flow chemistry system, a 2mL solution containing arylboronic acid (0.8mmol) and amine (2.4mmol) in acetonitrile was placed in 2mL sample loop A and 2mL solution containing TEMPO (1.2mmol) and acetic acid (1.6mmol) in acetonitrile was placed in 2mL sample loop B. The reactants were progressed through the copper column and SS coil reactor (0.30mL/min), with each sample loop/pump set at 0.15mL/min, and a 250psi back-pressure regulator and collected in a 100mL RB flask. The solvent removed and product purified with a Teledyne Combiflash Rf and silica gel column chromatography in ethyl acetate:hexane (typically 1:19) to yield an isolated product.

Molecular Weight:197.27
XLogP3:4.2
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:1
Rotatable Bond Count:2
Exact Mass:197.120449483
Monoisotopic Mass:197.120449483
Topological Polar Surface Area:12
Heavy Atom Count:15
Complexity:184
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes