[ CAS No. 4877-93-4 ] {[proInfo.proName]}

Name: 4877-93-4|2,2'-Dimethoxybiphenyl|97%
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Product Details of [ 4877-93-4 ]

CAS No. :	4877-93-4	MDL No. :	MFCD00067073
Formula :	C₁₄H₁₄O₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	VGMKUVCDINAAFC-UHFFFAOYSA-N
M.W :	214.26	Pubchem ID :	611816
Synonyms :

Safety of [ 4877-93-4 ]

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

Application In Synthesis of [ 4877-93-4 ]

* 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.

Upstream synthesis route of [ 4877-93-4 ]
Downstream synthetic route of [ 4877-93-4 ]

[ 4877-93-4 ] Synthesis Path-Upstream 1~1

1
[ 4877-93-4 ]
[ 528-43-8 ]

Reference： [1] Patent: WO2013/95361, 2013, A1,

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Yield	Reaction Conditions	Operation in experiment
98%	Stage #1: 2-bromoanisole With magnesium In tetrahydrofuran Inert atmosphere; Reflux; Stage #2: With dilithium tetrachlorocuprate(II); oxygen In tetrahydrofuran at 20℃; for 2h;
98%	With [1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene](3-chloropyridyl)palladium(ll) dichloride; isopropyllithium In toluene at 20℃; for 2h; Schlenk technique; Inert atmosphere;
98%	With DPEPhos; potassium <i>tert</i>-butylate; palladium diacetate; bis(pinacol)diborane for 12h; Heating;

95%	With (1E,2E)-N<SUP>1</SUP>,N<SUP>2</SUP>-bis(2,6-dimethylphenyl)ethane-1,2-diimine; nickel dibromide; zinc In tetrahydrofuran at 70℃; for 10h; Inert atmosphere;
93%	Stage #1: 2-bromoanisole With magnesium In tetrahydrofuran at 20℃; for 3h; Inert atmosphere; Stage #2: With synthetic air; cobalt(II) chloride In tetrahydrofuran at 0℃; for 3h; Inert atmosphere;
91%	With manganese; zirconocene dichloride; [(2,9-dimethyl-1,10-phenanthroline)dichloro nickel(II)]; lithium chloride In 1,2-dimethoxyethane at 20℃; for 4h; Inert atmosphere;	General procedure: To a suspension of a NiCl2-complex (0.01 mmol, 0.02 equiv), Zr(cp)2Cl2 (Strem, 99%; 7.3 mg, 0.025 mmol, 0.05 equiv), Mn powder (Aldrich, 99.99%; 54.9 mg, 1.0 mmol, 2.0 equiv) and LiCl (Aldrich, anhydrous, ground powder; 42.4 mg, 1.0 mmol, 2.0 equiv) in DME (Aldrich, anhydrous, 99.5%; 1.0 mL) was added an iodide (0.5 mmol) under nitrogen. The mixture was stirred at rt under nitrogen until the reaction completed (TLC). Except for the dipyridyls, the mixture was loaded on silica gel directly, and the flash chromatography on silica gel gave the homo-coupling product. For dipyridyls, the reaction was quenched with aq. NH4OH (27% w/w, 0.6 mL), stirred for 10 min, extracted with CH2Cl2 (10 mL × 3), washed with brine (15 mL), dried over Na2SO4, filtered, and concentrated under reduced pressure. The residue was purified by flash chromatography on silica gel to give the homocoupling product. For alkenyl halide substrates (Fig. 3 and Table 3), the reaction was done in 0.2 mmol scale (C: 0.5 M) with added toluene (42 μl, 0.4 mmol, 2.0 equiv) as an internal standard. After the reaction was completed, a small portion (50 μL) of the mixture was passed through a small silica pad, and eluted with CDCl3 (1 mL). The yield was estimated from 1H NMR (600 MHz, CDCl3).
90%	Stage #1: 2-bromoanisole With iodine; magnesium In tetrahydrofuran for 1h; Reflux; Stage #2: With copper(l) cyanide In tetrahydrofuran at 20℃; for 0.166667h; Stage #3: With 1,2,3,4,5,6,7,8-octahydro[1,4:5,8]dimethano-9,10-anthraquinone In tetrahydrofuran for 4h;
90%	With [1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene](3-chloropyridyl)palladium(ll) dichloride; tert.-butyl lithium In n-heptane at 20℃; for 0.166667h; Schlenk technique;
90%	Stage #1: 2-bromoanisole With tert.-butyl lithium; manganese(ll) chloride In tetrahydrofuran; pentane at -78℃; for 0.333333h; Inert atmosphere; Schlenk technique; Stage #2: In tetrahydrofuran; pentane at 25℃; for 1h; Inert atmosphere; Schlenk technique;
87%	Stage #1: 2-bromoanisole With tert.-butyl lithium In diethyl ether at -78℃; Stage #2: In diethyl ether Stage #3: With Duroquinone In diethyl ether
87.7%	With palladium 10% on activated carbon; potassium acetate; bis(pinacol)diborane In ethanol at 60℃; for 3h; Inert atmosphere;	General procedure: General procedure: To a solution of brominated aromatic compounds (1 equiv),bis(pinacolate)diboron (1.5 equiv) and anhydrous ethanol (15 mL)were added10%palladium-carbon (0.01 equiv), followed by potassium acetate (3 equiv) under argon. The mixture was heated in a 60 °C with stirring for the indicated time. Thereactor was cooled to room temperature, and the reaction mixture was filtered, and thefiltrate was concentrated under reduced pressure. The residue was extracted with dichloromethane (20 mL×3), and organic layer was washed with water (20 mL×2)and once with brine (25 mL), dried over magnesium sulfate and concentrated in vacuo.The product was purified by silica gel flash chromatography on silica gel usingpetroleum as eluent.
86%	Stage #1: 2-bromoanisole With iodine; magnesium In diethyl ether at 20℃; for 0.666667h; Green chemistry; Stage #2: With C₂₁H₁₅N₃NiO₃S₅^(1-)*Na⁽¹⁺⁾; oxygen In diethyl ether at 20℃; for 5h; Green chemistry;
85%	With potassium carbonate In water; isopropyl alcohol at 40℃; for 3h;
82%	With monophosphine 1,2,3,4,5-pentaphenyl-1'-(di-tert-butylphosphino)ferrocene; (C₅H₅)2Zr(OC₄H₈)N(Si(CH₃)3)CH(C₆H₅); bis(dibenzylideneacetone)-palladium⁽⁰⁾ In toluene at 80℃; for 16h; Sealed tube; Inert atmosphere;
81%	In tetrahydrofuran at 50℃; for 46h;
81%	With potassium carbonate In ethanol; water at 80℃; for 4h; Schlenk technique; Sealed tube;
80%	Stage #1: 2-bromoanisole With magnesium In diethyl ether at 20℃; for 0.5h; Stage #2: With zinc dibromide In diethyl ether at 20℃; for 4h;
80%	With palladium diacetate; bis(tri-n-butyltin); cesium fluoride; tricyclohexylphosphine In neat (no solvent) at 110℃; for 24h;	General procrdure A screw-cap vial equipped with a magnetic stir bar was charged with aryl halide (1 mmol), hexa-n-butylditin (0.5 mmol),palladium acetate (0.01 mmol) and tricyclohexylphosphine (0.02 mmol),followed by anhydrous cesium fluoride (1.5 mmol). The resulting mixture was manually homogenized with a magnet. A vial was transferred to a preheated oil bath (110 °C). After 24 h, the mixture was cooled, dissolved in CH2Cl2-H2O mixture (1:1), the organic phase was separated, the solvent was evaporated in vacuo and the product was isolated by flash chromatography on a silica gel by elution with hexane-CH2Cl2 mixture.
79%	Stage #1: 2-bromoanisole With oxygen; magnesium In diethyl ether at 20℃; for 0.666667h; Green chemistry; Stage #2: With C₅₄H₄₆ClN₃NiO₃P₂ In diethyl ether at 20℃; for 5h; Green chemistry;
76%	Stage #1: 2-bromoanisole With n-butyllithium In tetrahydrofuran; hexane at 0℃; for 0.000861111h; Stage #2: With iron(III) chloride In tetrahydrofuran; hexane at 0℃; for 0.00193889h; Stage #3: With methanol In tetrahydrofuran; hexane at 0℃; for 0.000436111h;
75%	With tert.-butyl lithium; triethylamine; iron(II) chloride In tetrahydrofuran at -78 - 25℃; for 4h; Inert atmosphere;
74%	With NaH-t-AmONa-Ni(OAc)2-bpy In tetrahydrofuran at 63℃; for 0.5h;
74%	With D-Glucose; caesium carbonate In water for 24h;
72%	With tetrabutyl ammonium fluoride In tetrahydrofuran; N,N-dimethyl-formamide at 90℃; for 12h;
72%	Stage #1: 2-bromoanisole With magnesium In diethyl ether at 20℃; for 0.666667h; Stage #2: With C₃₉H₃₂ClOP₂RuS₅ In diethyl ether at 20℃; for 6h;
67%	With [Pd{C6H3(CH2CH2NH2)-4-OMe-5-κ2-C,N}(μ-Br)]2; potassium carbonate In N,N-dimethyl-formamide at 130℃; for 19h;
58%	Stage #1: 2-bromoanisole With magnesium In tetrahydrofuran at 20℃; for 0.5h; Stage #2: With titanium tetrachloride In tetrahydrofuran; 1,2-dimethoxyethane at 0℃; for 0.5h;
56%	With bis(bipyridine)nickel(II) bromide; ethylene dibromide; sodium iodide In N,N-dimethyl-formamide at 20℃; for 3h; Electrochemical reaction; Inert atmosphere;	General procedure: DMF (40 mL), NaI (375 mg, 2.5 mmol), and 1,2-dibromoethane (100μL, 1.16 mmol) were added to an undivided electrochemical cell, fitted with an iron/nickel (64/36) anode, and surrounded by a nickel foam as the cathode (surface: 40 cm2, porosity: 500 μm, Goodfellow).The mixture was electrolyzed under argon at a constant current intensityof 0.2 A at r.t. for 15 min. The current was then stopped, then NiBr2bpy (187 mg, 0.5 mmol) and aryl or heteroaryl halide (5 mmol),were sequentially added. The solution was electrolyzed at 0.2 A untilthe starting aryl or heteroaryl halide had been totally consumed (2-5h). Sat. aq EDTA-Na2 solution (50 mL) was added, and the resultingsolution was extracted either with EtOAc (for aryl halides) or withCH2Cl2 (for heteroaryl halides) (3 × 50 mL). The combined organic layerswere washed with brine (50 mL), dried (MgSO4), filtered, and concentratedunder vacuum. The crude product was purified by flashchromatography (silica gel, 70-200 μm).
45%	With tris(dibenzylideneacetone)dipalladium ⁽⁰⁾; sodium t-butanolate In diethylene glycol dimethyl ether at 130℃; for 12h;
32%	With manganese; (1E,2E)-N<SUP>1</SUP>,N<SUP>2</SUP>-bis(2,6-dimethylphenyl)ethane-1,2-diimine; trifluoroacetic acid; cobalt(II) bromide In acetonitrile at 20℃; for 48h;
28%	With iron; sodium bromide In methanol; ethanol Electrolysis;
24%	With zinc In 1,2-dimethoxyethane; water at 45℃; for 1.5h; ultrasound irradiation;
19%	With n-butyllithium In tetrahydrofuran; hexane at -78 - 20℃; for 19h;
	With n-butyllithium; diethyl ether; cobalt(II) bromide
45 % Turnov.	With [2,2]bipyridinyl; potassium iodide In various solvent(s) Ambient temperature; electrochemical coupling;
	With n-butyllithium; Trimethyl borate; sodium carbonate 1) THF, -78 deg C -> room temperature, 4 h; room temperature, overnight, 2) THF, EtOH, H2O, toluene, reflux, 24 h; Yield given. Multistep reaction;
	Stage #1: 2-bromoanisole With iodine; magnesium Stage #2: With 4-oxo-2,2,6,6-tetramethylpiperidin-oxyl In tetrahydrofuran at 66℃; for 0.333333h; Inert atmosphere;
64.58 %Chromat.	With ethanol; 1% Pd/C; cesium fluoride In dimethyl sulfoxide at 120℃; for 66h; Inert atmosphere;
	Stage #1: 2-bromoanisole With iodine; magnesium In diethyl ether at 20℃; for 0.666667h; Stage #2: With C₂₀H₁₆NNiO₇S₆^(1-)*Na⁽¹⁺⁾; oxygen In diethyl ether at 20℃; for 5h; chemoselective reaction;
	Multi-step reaction with 2 steps 1: cobalt(II) bromide; 3-chloroprop-1-ene; trifluoroacetic acid / acetonitrile / 20 °C 2: cobalt(II) bromide; p-benzoquinone / acetonitrile / 20 °C

Yield	Reaction Conditions	Operation in experiment
95%	With [1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene](3-chloropyridyl)palladium(ll) dichloride; tert.-butyl lithium In toluene at 20℃; for 1h; Schlenk technique; Inert atmosphere;
89%	With tetrabutyl ammonium fluoride In tetrahydrofuran; N,N-dimethyl-formamide at 90℃; for 12h;
89%	With palladium diacetate In ethanol at 80℃; for 5h; Green chemistry; chemoselective reaction;

88%	With indium In N,N-dimethyl-formamide for 11h; Heating;
86%	With sodium hydroxide; ammonium formate; zinc In methanol for 4h; Heating;
84%	With sodium hydroxide; triethylammonium formate; zinc In methanol for 5h; Heating;
84%	With D-Glucose; caesium carbonate In water for 24h;
82%	With caesium carbonate; hydroquinone In N,N-dimethyl acetamide at 100℃; for 48h;
82%	With potassium acetate In ethanol; dimethyl sulfoxide at 120℃; for 20h; Schlenk technique; Inert atmosphere;	Typical procedure for the Ullmann coupling reaction General procedure: palladium catalyst (1.0 mol%) and KOAc (3 mmol) were placed in an oven dried 25 mL Schlenk tube, and the reaction vessel was evacuated and filled with nitrogen for three times. Aromatic halide (0.5 mmol), and solvent (5.0 mL) were added with a syringe, and the resulting mixture was stirred at 120 °C for a desired time. After cooled down to room temperature, the reaction mixture was filtered and washed with brine and diethyl ether. The combined organic layers were washed with a saturated solution of sodium hydrogen carbonate and then with brine, dried over Na2SO4. Solvent was removed under a reduced pressure, and the reaction products were purifiedby silica gel chromatography with a mixture of n-hexane and ethyl acetate.
81%	With palladium diacetate; bis(tri-n-butyltin); cesium fluoride; tricyclohexylphosphine In neat (no solvent) at 110℃; for 24h;	General procrdure A screw-cap vial equipped with a magnetic stir bar was charged with aryl halide (1 mmol), hexa-n-butylditin (0.5 mmol),palladium acetate (0.01 mmol) and tricyclohexylphosphine (0.02 mmol),followed by anhydrous cesium fluoride (1.5 mmol). The resulting mixture was manually homogenized with a magnet. A vial was transferred to a preheated oil bath (110 °C). After 24 h, the mixture was cooled, dissolved in CH2Cl2-H2O mixture (1:1), the organic phase was separated, the solvent was evaporated in vacuo and the product was isolated by flash chromatography on a silica gel by elution with hexane-CH2Cl2 mixture.
77.5%	With indium In N,N-dimethyl-formamide at 100℃; for 24h;
69%	With palladium diacetate; potassium carbonate In butanone at 120℃; for 5h; Inert atmosphere;
65%	With D-Glucose; gold(lll) acetate; tetrabutylammonium acetate at 90℃; for 15h;
60%	With trimethylsilylmethyllithium; manganese(ll) chloride In tetrahydrofuran at -78 - 20℃; for 10h; Inert atmosphere; Schlenk technique;
58%	With copper(I) thiophene-2-carboxylate; copper In dimethyl sulfoxide at 65℃;	4.2 General procedure for the modified Cu(0)-Cu(I)-mediated Ullmann biaryl coupling General procedure: (0013) A mixture of aryl halide (1 equiv), Cu(0) powder (10 equiv), and CuTC (2 equiv) in DMSO (0.2 mL/mmol of aryl halide) was stirred at 65-70 °C for 15-72 h. Water and EtOAc were added, and the two phases were separated. The aqueous layer was extracted twice with EtOAc. The combined organic layers were washed with brine, dried over Na2SO4, filtered, and concentrated under reduced pressure to give the crude product which was further purified by preparative TLC (EtOAc/hexanes) to furnish the desired product.
54%	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate; bis(pinacol)diborane In dimethyl sulfoxide at 80℃; for 14h;
52%	With potassium carbonate In N,N-dimethyl-formamide at 140℃; for 48h;
43%	With potassium phosphate; gold In N,N-dimethyl-formamide at 130℃; for 48h;
40%	With 18-crown-6 ether; zinc In water at 20℃;
	With sodium; xylene man erhitzt dann auf 180-200grad;
	With copper at 210 - 260℃;
	With p-nitrobenzene iodide; copper In N,N-dimethyl-formamide
9 % Chromat.	With Tetrakis(dimethylamino)ethylen; [bmim]PF₆; phenylacetylene at 120℃; for 2h;
73 % Chromat.	With zinc In water; acetone at 20℃;
46.94 %Chromat.	With ethanol; 1% Pd/C; cesium fluoride In dimethyl sulfoxide at 120℃; for 66h; Inert atmosphere;
	Multi-step reaction with 2 steps 1: toluene / 13 h / 50 °C 2: silver tetrafluoroborate / acetone / 1 h / 20 °C
	With tetrabutylammomium bromide; palladium diacetate; potassium hydroxide; CyJohnPhos In methanol; water at 100℃; for 1.5h; Microwave irradiation; Inert atmosphere;
	Multi-step reaction with 2 steps 1: tellurium; potassium hydroxide / dimethyl sulfoxide / 10 h / 110 °C / Inert atmosphere; Sealed tube 2: palladium dichloride; sodium carbonate; silver(l) oxide / methanol / 2 h / 20 °C
15 %Spectr.	With 2,4,6-tris(4-methoxyphenyl)-1-(3-phenylpropyl)pyridin-1-ium tetrafluoroborate; C₃₆H₄₈Br₂N₄Ni; tetrakis(azepano)ethylene In N,N-dimethyl acetamide at 80℃; for 24h; Inert atmosphere; Glovebox;

[ CAS No. 4877-93-4 ] {[proInfo.proName]}

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[ 4877-93-4 ] Synthesis Path-Upstream 1~1

[ 4877-93-4 ] Synthesis Path-Downstream 1~88

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Yield	Reaction Conditions	Operation in experiment
97%	Stage #1: 2,2'-dihydroxybiphenyl With potassium carbonate In acetone at 20℃; for 0.166667h; Inert atmosphere; Stage #2: dimethyl sulfate In acetone at 20℃; for 12h; Inert atmosphere;
95%	With potassium carbonate at 60℃; for 1.5h;
95%	With sodium hydroxide	1 Example 1: Synthesis of magnolol (5,5'-diallyl-biphenyl-2,2'-diol) [0012] 2,2'-Biphenol is reacted in sodium hydroxide with dimethyl sulfate for 1-2 hours to give 2,2'-bianisole (95% yield). Solid is separated, washed with water and dried at 60-65°C. [0013] 2,2'-bianisole is efficiently brominated to give 4,4'-Dibromo-2,2'-bianisole which is then reacted with allyl bromide in THF to obtain 4,4'-Diallyl-2,2'-bianisole. [0014] The 4,4'-diallyl-2,2'-bianisole is added to a mixture of aluminum chloride, thiourea and 1 ,2-dichloroethane slowly over 3 hours at 50°C. Temperature and stirring is maintained for an additional 3-4 hours. Reaction mix is cooled and added to HC1 and phases are separated. The organic layer is added to charcoal, filtered and the solvent distilled, to obtain the title compound.

95%	With sodium hydroxide	1 Synthesis of Magnolol (5,5'-diallyl-biphenyl-2,2'-diol) 2,2′-Biphenol is reacted in sodium hydroxide with dimethyl sulfate for 1-2 hours to give 2,2′-bianisole (95% yield). Solid is separated, washed with water and dried at 60-65° C. [0023] 2,2′-bianisole is efficiently brominated to give 4,4′-Dibromo-2,2′-bianisole which is then reacted with allyl bromide in THF to obtain 4,4′-Diallyl-2,2′-bianisole. [0024] The 4,4′-diallyl-2,2′-bianisole is added to a mixture of aluminum chloride, thiourea and 1,2-dichloroethane slowly over 3 hours at 50° C. Temperature and stirring is maintained for an additional 3-4 hours. Reaction mix is cooled and added to HCl and phases are separated. The organic layer is added to charcoal, filtered and the solvent distilled, to obtain the title compound.
	With alkali
	With sodium hydroxide
	With sodium hydroxide
	With sodium hydroxide	1 Example I: Synthesis of tetrahydro-magnolol (5,5 '-dipropyl-biphenyl-2,2'-diol) [0012] Protection: Biphenol is reacted in sodium hydroxide with sodium sulfate for 1 -2 hours. Solid is separated, washed with water and dried at 60-65 °C [0013] Acylation: Combine propionyl chloride with anhydrous aluminum chloride in 1 ,2- dichloroethane. Add bianisole at room temperature and allow to stir for 4-6 hours. Quench in diluted hydrochloric acid and separate organic layer. Remove solvent via distillation and crystallize from methanol. [0014] Reduction: Reflux 3-5 hours the 4,4'-dipropionyl 2,2'-bianisole in hydrochloric acid with zinc powder. Remove methanol and add ethyl acetate with stirring. Remove zinc by filtration and solvent by distillation. [0015] De-methylation: Add the product of the previous step to a mixture of aluminum chloride, thiourea and 1 ,2-dichloroethane slowly over 3 hours at 50°C. Maintain temperature and stirring for an additional 3-4 hours. Cool reaction and add to hydrochloric acid and separate phases. Add organic layer to charcoal, filter and distill solvent to recover title compound. [0016] The overall yield is about 55%, with a purity of greater than 98%.

Yield	Reaction Conditions	Operation in experiment
87%	With potassium carbonate In N,N-dimethyl-formamide
85%	With potassium hydroxide In dimethyl sulfoxide at 20℃;
80%	With potassium hydroxide In acetone for 16h; Inert atmosphere;

	With potassium hydroxide; water at 100℃; im Druckrohr;
	With potassium carbonate In acetone at 80℃;

Yield	Reaction Conditions	Operation in experiment
94%	With iron(III) chloride; 1,2-dichloro-ethane In tetrahydrofuran at 0℃; for 0.0833333h; Ionic liquid; Inert atmosphere;
88%	With iron(III) chloride; 1,2-dichloro-ethane In diethyl ether for 1h; Heating;
81%	With iron(III) chloride; 1,2-dichloro-ethane In tetrahydrofuran at 20℃; for 4h;

80%	With [2,2]bipyridinyl; oxygen; iron(III) chloride In tetrahydrofuran at 20℃; for 0.166667h;
79%	With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical In tetrahydrofuran at 66℃; for 0.333333h; Inert atmosphere;
74%	With 1,2-dichloro-2-methylpropane; 0.5C₄H₈OC₂₄H₂₀B^(1-)C₃₆H₆₄CoN₈⁽¹⁺⁾ In tetrahydrofuran at -116 - 50℃; for 6h; Inert atmosphere;
63%	With C₂₉H₃₃Cl₂FeN₅*C₄H₈O In tetrahydrofuran; diethyl ether at 20℃; for 0.5h; Inert atmosphere; Schlenk technique;
	(i) CrCl₃, THF, (ii) but-2-yne; Multistep reaction;
	With manganese chloride bis(lithium chloride); air In tetrahydrofuran at 20℃; for 0.75h;

Yield	Reaction Conditions	Operation in experiment
1: 21 % Chromat. 2: 77%	With NaH-t-AmONa-Ni(OAc)2-bpy In tetrahydrofuran at 63℃; for 0.583333h;
1: 73% 2: 11%	With palladium diacetate In ethanol at 80℃; for 6h; Green chemistry; chemoselective reaction;
1: 47.4% 2: 4.9%	With (C₅H₅)2Zr(OC₄H₈)N(Si(CH₃)3)CH(C₆H₅); tri-tert-butyl phosphine; bis(dibenzylideneacetone)-palladium⁽⁰⁾ In toluene at 100℃; for 16h; Sealed tube; Inert atmosphere;

1: 36% 2: 7%	With sodium hydroxide; sodium formate In water at 60℃; for 4h; use of α- and γ-cyclodextrin as catalyst;
9%	With sodium hydroxide; sodium formate In water at 60℃; for 4h;
1: 91 %Chromat. 2: 9 %Chromat.	With tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; JohnPhos; isopropyllithium In toluene at 22℃; for 1h; Schlenk technique; Inert atmosphere;

Yield	Reaction Conditions	Operation in experiment
94%	With 1-dodecyl-3-methylimidazolium cuprous chloride; copper; zinc at 90℃; for 4h;
93%	With potassium <i>tert</i>-butylate; palladium diacetate; bis(pinacol)diborane; XPhos for 12h; Heating;
91%	With NaH-t-AmONa-Ni(OAc)2-bpy In tetrahydrofuran at 63℃; for 3h;

78%	With phenyllithium In tetrahydrofuran
70%	With potassium phosphate; bis(pinacol)diborane In 1,4-dioxane at 110℃; for 15h;
69%	With (i-Pent₂(C₆H₃))2(C₃H₂N₂))PdCl₂((C₅H₄N)Cl); tert.-butyl lithium In toluene at 20℃; for 1h; Schlenk technique; Inert atmosphere;
68%	With potassium phosphate tribasic heptahydrate; chloro(2-dicyclohexylphosphino-2’,4’,6’-triisopropyl-1,1‘-biphenyl)[2-(2’-amino-1,1‘-biphenyl’)]palladium(II); bis(pinacol)diborane; XPhos In ethanol at 20℃; for 8h;
66%	With D-Glucose; caesium carbonate In water for 24h;
57%	With styrene; [2,2]bipyridinyl; sodium hydride In tetrahydrofuran for 3.5h; Heating;
91 % Turnov.	With [2,2]bipyridinyl; potassium iodide In various solvent(s) Ambient temperature; electrochemical coupling;
	With 4,4'-bis(carbomethoxy)-2,2'-bipyridine; 4,4'-di-tert-butyl-2,2'-bipyridine; zinc In N,N-dimethyl acetamide at 70℃; for 4h; Inert atmosphere;	13 Example 13 To a reaction container made of glass and equipped with a cooling apparatus, 7.6 mg of nickel bromide, 4.7 mg of 4,4'-bis(1,1-dimethylethyl)-2,2'-bipyridine, 4.7 mg of 4,4'-bis(methoxycarbonyl)-2,2'-bipyridine and 96.1 mg of zinc powder were added in an atmosphere of nitrogen at room temperature. To the mixture obtained, 100 mg of 2-chloroanisole and 5 mL of N,N-dimethylacetamide were added at room temperature. The reaction was conducted by stirring the mixture obtained at 70° C. for 4 hours to obtain a reaction mixture containing 2,2'-dimethoxybiphenyl. The yield of 2,2'-dimethoxybiphenyl was 26 mg.

Yield	Reaction Conditions	Operation in experiment
97.5%	With aluminium trichloride In ethanethiol for 0.5h; Ambient temperature;
97.5%	With aluminium trichloride In ethanethiol for 0.5h; Ambient temperature;
97%	With potassium <i>tert</i>-butylate; diphenylphosphane In N,N-dimethyl-formamide at 80℃; for 12h; Sealed tube;

Yield	Reaction Conditions	Operation in experiment
	With aluminium trichloride In dichloromethane for 12h; Ambient temperature; Yield given;
	With aluminum (III) chloride In 1,2-dichloro-ethane at 20℃;	1 Example I: Synthesis of tetrahydro-magnolol (5,5 '-dipropyl-biphenyl-2,2'-diol) [0012] Protection: Biphenol is reacted in sodium hydroxide with sodium sulfate for 1 -2 hours. Solid is separated, washed with water and dried at 60-65 °C [0013] Acylation: Combine propionyl chloride with anhydrous aluminum chloride in 1 ,2- dichloroethane. Add bianisole at room temperature and allow to stir for 4-6 hours. Quench in diluted hydrochloric acid and separate organic layer. Remove solvent via distillation and crystallize from methanol. [0014] Reduction: Reflux 3-5 hours the 4,4'-dipropionyl 2,2'-bianisole in hydrochloric acid with zinc powder. Remove methanol and add ethyl acetate with stirring. Remove zinc by filtration and solvent by distillation. [0015] De-methylation: Add the product of the previous step to a mixture of aluminum chloride, thiourea and 1 ,2-dichloroethane slowly over 3 hours at 50°C. Maintain temperature and stirring for an additional 3-4 hours. Cool reaction and add to hydrochloric acid and separate phases. Add organic layer to charcoal, filter and distill solvent to recover title compound. [0016] The overall yield is about 55%, with a purity of greater than 98%.

Yield	Reaction Conditions	Operation in experiment
94%	With bromine In chloroform at 0℃; for 12h;
90%	With N-Bromosuccinimide In N,N-dimethyl-formamide for 12h; Ambient temperature;
85%	With N-Bromosuccinimide In chloroform Heating;

80%	With sulfuric acid; 3,3-dimethyldioxirane; sodium bromide In acetone
80%	With N-Bromosuccinimide In N,N-dimethyl-formamide at 20℃; for 12h;
	With bromine	1 Example 1: Synthesis of magnolol (5,5'-diallyl-biphenyl-2,2'-diol) [0012] 2,2'-Biphenol is reacted in sodium hydroxide with dimethyl sulfate for 1-2 hours to give 2,2'-bianisole (95% yield). Solid is separated, washed with water and dried at 60-65°C. [0013] 2,2'-bianisole is efficiently brominated to give 4,4'-Dibromo-2,2'-bianisole which is then reacted with allyl bromide in THF to obtain 4,4'-Diallyl-2,2'-bianisole. [0014] The 4,4'-diallyl-2,2'-bianisole is added to a mixture of aluminum chloride, thiourea and 1 ,2-dichloroethane slowly over 3 hours at 50°C. Temperature and stirring is maintained for an additional 3-4 hours. Reaction mix is cooled and added to HC1 and phases are separated. The organic layer is added to charcoal, filtered and the solvent distilled, to obtain the title compound.

Yield	Reaction Conditions	Operation in experiment
95%	With bromo-phenyl-acetic acid methyl ester; potassium fluoride; dichloro[2,2'-bis(diphenylphosphino)-1,1'-binaphthyl]palladium(II) In 1,4-dioxane; water at 100℃;
95%	With copper fluorapatite In methanol at 20℃; for 2h; Green chemistry;
88%	With potassium acetate; silver(l) oxide In methanol at 60℃; for 20h;	6.2 Typical experimental procedure for homocoupling of arylboronic acids General procedure: A mixture of arylboronic acid 3 (0.2 mmol), nano-Pd (0.1mol% Pd), Ag2O (45 mol%), KOAc (1 equiv), and CH3OH (0.8mL) was stirred at 40 oC until complete consumption of starting materialas judged by TLC. After the mixture was filtered and evaporated, the residue was purified by flash column chromatography to afford the corresponding homocoupling product 4 (petroleum ether or petroleum ether/ethyl acetate).

88%	With palladium diacetate at 20℃; for 0.5h;
86%	With oxygen; potassium carbonate In water at 25℃; for 2h; Green chemistry;	Representative procedure for the nano CuO catalyzed homocoupling of arylboronic acid General procedure: A solution of nano CuO (0.010 mmol) and substituted phenylboronic acid (1 mmol) in H2O (2 mL) was stirred at 25 °C for 2 h under aerobic condition. After the reaction was over, the reaction mixture was extracted with ethyl acetate and washed with doubledistilled water in a separating funnel. The organic layer was separated and collected in a conical flask. After evaporation of the solvent in a rotary evaporator, reaction mixture was subjected to column chromatography on silica gel column (ethyl acetate/hexane, 1:10) to afford the respective product.
85%	With potassium carbonate In water at 20℃;
82%	With sodium hypochlorite; tetrabutylammomium bromide; palladium dichloride In water at 70℃;
76%	With molecular sieve; oxygen In dimethyl sulfoxide at 50℃; for 24h;
71%	With potassium permanganate; potassium carbonate In methanol; water at 20℃;
69.6%	With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; sodium carbonate; 2-bromo-1,3-bis-(trifluoromethyl)-benzene In 1,4-dioxane; water at 90℃; for 2h; Sealed tube; Inert atmosphere;	Biphenyl-4,4′-dicarbaldehyde (14a); Typical HC Procedure General procedure: A crimp-cap vial equipped with magnetic stirrer bar wascharged with (dppf)PdCl2·CH2Cl2 (8.2 mg, 0.010 mmol), (4-formylphenyl)boronic acid (2a; 97.9 mg, 0.653 mmol), Na2CO3(69.2 mg, 0.653 mmol), and 2-bromo-1,3-bis(trifluoromethyl)benzene (6; 95.7 mg, 0.327 mmol). The vial was sealedwith a crimp-cap septum and filled with Ar by using threevacuum-purge cycles. Degassed (Ar sparge) 1,4-dioxane (0.70mL) and H2O (0.25 mL) were added, and the vial was immersedin an oil bath at 90 °C for 2 h, then cooled to r.t. H2O was addedand the mixture was extracted with CH2Cl2 (2 × 4 mL). The combinedorganics were mixed with PhCF3 (60.0 L, 0.488 mmol) asan added standard, and an aliquot was diluted in CDCl3 forquantitative 19F NMR spectroscopy. The organics were thendried (Na2SO4) and concentrated in vacuo. Purification by flashchromatography [silica gel, hexanes-EtOAc (0-25%)] gave awhite solid; yield: 53.2 mg (77%); mp 141-143 °C; Rf = 0.26 (25%EtOAc-hexanes).
68%	With chromium dichloride; silver(l) oxide In tetrahydrofuran at 65℃;
67%	With potassium phosphate In N,N-dimethyl-formamide at 100℃; for 24h;
65%	With palladium(II) complex of ferrocene appended N-heterocyclic carbene supported on silica; air In water at 20℃; for 11h;	2.4 General Procedure for Synthesis of Biaryls General procedure: A suspension of aryl boronic acid (5) (0.5mmol, 0.0610g) and SilFemBenzNHCPd complex (4) (50mg) in water(5mL) was stirred at room temperature. After completion of the reaction as monitored by thin layer chromatography(TLC), the insoluble complex was filtered and washed with copious amount of water. The filtrate was extracted withethyl acetate (3 × 5mL). The combined extracts were driedover Na2SO4 and evaporated under reduced pressure. The residue was purified by column chromatography over silicagel to give pure biaryls which were characterized by FT-IR,1H-NMR, 13C-NMR and mass spectroscopy.
63%	With palladium diacetate; triphenylphosphine at 70℃; for 8h;
60%	With [Cu(trans-cyclohexane-1,2-diamine)₂(H₂O)₂][OTf]₂ In methanol at 20℃; for 3h;	2.3. General procedure for synthesis of biaryls General procedure: In a 25-mL round-bottomed flask, a solution of copper(II)complex (2 mol %) and substituted phenylboronic acid (1.5 mmol)in methanol (5 mL) was stirred at room temperature for 3e4 h. Theprogress of the reaction was monitored by TLC. After completion ofthe reaction, the solvent was removed and the product was washedwith water and extracted with ethyl acetate (3 10 mL). Thecombined organic layers were dried over Na2SO4 and the solventremoved under reduced pressure to give crude product which waspurified by column chromatography by using petroleum ether/ethyl acetate (4:1) as an eluent.
50%	With air In methanol at 20℃;
44%	With copper diacetate In N,N-dimethyl-formamide at 100℃;
42%	With air; [{(1,10-phenanthroline)Cu(μ-OH)}2Cl2]*3H2O In isopropyl alcohol at 28℃; for 2h;
37%	With iodine; oxygen; potassium carbonate In PEG-400 at 140℃; for 48h;
	With tetrabutylammomium bromide; potassium carbonate In water
	With Au₀₀₀₆Mg_2.77AlO_3.71(OH)1.12; oxygen In methanol at 100℃; for 12h; Autoclave;	2.4 Catalytic tests General procedure: Aerobic couplings of phenylboronic acids were performed in a high-pressure autoclave with a magnetic stirrer (1200 rpm). The solid catalysts and substrates were both dried under vacuum for 3 h before the catalytic reactions. Typically, the substrate, catalyst, and solvent were mixed in the reactor and stirred for 1 h at room temperature. Then, the reaction system was heated to a given temperature (the temperature was measured with a thermometer in an oil bath) and oxygen was introduced and kept at the desired pressure. After the reaction, the product was taken out of the reaction system and analyzed by gas chromatography (GC-17A and GC-14C, Shimadzu, using a flame ionization detector) with a flexible quartz capillary column coated with OV-17 and FFAP. The conversion of phenylboronic acids and the product selectivities were obtained from the product yields, which were established by an internal standard. As a typical run for isolation of biphenyl, after removal of the catalyst from the reaction mixture, the methanol solvent was evaporated from the filtrate, giving a white solid. The solid obtained was treated by column chromatography on silica gel (∼200 mesh) with petroleum ether as eluent. After evaporation of the petroleum ether, the biphenyl product was obtained. The recyclability of the catalyst was tested by separating it from the reaction system by centrifugation, washing with a large quantity of methanol, and drying at 100 °C for 6 h.
42 %Chromat.	With [Cu₂Br₂(bis[3,5-dimethyl-4-(4'-pyridyl)pyrazol-1-yl]methane)]_n*nH₂O} In N,N-dimethyl-formamide at 20℃; for 6h; Inert atmosphere;

Yield	Reaction Conditions	Operation in experiment
85%	With tert.-butyl lithium; triethylamine; iron(II) chloride In tetrahydrofuran at -78 - 25℃; for 4h; Inert atmosphere;
75%	Stage #1: methoxybenzene With n-butyllithium; N,N,N,N,-tetramethylethylenediamine In diethyl ether; hexane at 20℃; for 2h; Stage #2: With copper(I) bromide dimethylsulfide complex; lithium bromide In tetrahydrofuran; diethyl ether; hexane Stage #3: With (3,5-dinitrophenyl)(4-methylpiperazin-1-yl)methanone In tetrahydrofuran; diethyl ether; hexane
70%	Stage #1: methoxybenzene With tert.-butyl lithium; manganese(ll) chloride In tetrahydrofuran; pentane at -78℃; for 0.333333h; Inert atmosphere; Schlenk technique; Stage #2: In tetrahydrofuran; pentane at 25℃; for 1h; Inert atmosphere; Schlenk technique;

84 % Chromat.	Stage #1: methoxybenzene With n-butyllithium In tetrahydrofuran at -78 - 20℃; Stage #2: With zinc(II) iodide In tetrahydrofuran Stage #3: With N-chloro-succinimide In tetrahydrofuran at 45℃; for 15h;
	With potassium peroxodiphosphate; water In phosphate buffer UV-irradiation;

Yield	Reaction Conditions	Operation in experiment
40%	Stage #1: 2-methoxyphenyllithium With gallium(III) trichloride In diethyl ether Stage #2: In water; toluene at 25℃; for 0.0833333h; Further stages.;
84 % Chromat.	Stage #1: 2-methoxyphenyllithium With zinc(II) iodide In tetrahydrofuran at 0℃; for 1h; Stage #2: With N-chloro-succinimide In tetrahydrofuran at 45℃;

Yield	Reaction Conditions	Operation in experiment
94%	Stage #1: 2,2'-Dimethoxybiphenyl With n-butyllithium; N,N,N,N,-tetramethylethylenediamine In diethyl ether; hexane at 0 - 40℃; for 19h; Inert atmosphere; Stage #2: methyl iodide In diethyl ether; hexane at 0℃; for 1.5h; Inert atmosphere;
77%	Stage #1: 2,2'-Dimethoxybiphenyl With n-butyllithium; N,N,N,N,-tetramethylethylenediamine In diethyl ether; hexane at 0 - 40℃; for 17h; Stage #2: methyl iodide In diethyl ether; hexane at 0℃; for 1.5h; Further stages.;

[ CAS No. 4877-93-4 ] {[proInfo.proName]}

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[ 4877-93-4 ] Synthesis Path-Upstream 1~1

[ 4877-93-4 ] Synthesis Path-Downstream 1~88

Related Functional Groups of [ 4877-93-4 ]

Aryls

Ethers

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[ 4877-93-4 ]

Yield	Reaction Conditions	Operation in experiment
99%	With potassium carbonate; palladium dichloride In water; N,N-dimethyl-formamide at 20℃; for 0.166667h;
98%	With Ph₂P(CH₂CH₂O)22CH₃; triethylamine; palladium dichloride In water at 100℃; for 1h; Inert atmosphere;
89%	With potassium carbonate In isopropyl alcohol at 80℃; for 1h;

89%	With potassium carbonate In water; isopropyl alcohol at 80℃; for 1h;	2.1.5 2) Examples of Synthesis by Suzuki Cross-Couplings 2-1) Reaction between arylbromide and boronic acid The arylbromide and boronic acid shown in TABLE 4 were allowed to react with each other under the reaction conditions shown in TABLE 4, using the Pd-containing perovskite-like composite oxide produced in Example of production 1 as the catalyst for synthesis reaction. Yields in the respective reactions are shown in TABLE 4.
80%	With potassium carbonate In ethanol at 20℃; for 4h; in air;
71%	With potassium carbonate In ethanol; toluene at 80℃;
62%	With palladium 10% on activated carbon; tetra-n-butylammoniumfluoride trihydrate at 150℃; for 0.5h; Microwave irradiation; Inert atmosphere;
49%	With potassium hydroxide In methanol at 70℃; for 12h;
	With dichloro[1,1'-bis(di-t-butylphosphino)ferrocene]palladium(II); potassium carbonate In water; acetonitrile at 60℃; Inert atmosphere; Sealed vessel;	4.6. Typical preparative procedure Typical preparative procedures were performed on 10.0 mmol scale using a Mettler-Toledo FlexiWeigh 30 automated solid handling unit to pre-weigh the aryl halide (10.0 mmol, 1.0 equiv), aryl boronic acid (12.0 mmol, 1.2 equiv) and Pd-118 (65.2 mg, 0.1 mmol, 1.0 mol %). Acetonitrile (10.0 mL) was added, followed by K2CO3 added as a stock aqueous solution (10.0 mL water containing 2.07 g, 15.0 mmol, 1.5 equiv). NB. No internal standard was added for preparative reactions. Reaction mixtures were sealed under a N2 atmosphere and heated to 60 °C with magnetic stirring. HPLC analysis showed that reactions using aryl bromides were complete within 1 h but that aryl chlorides typically required 24 h.After reaction mixtures had cooled to room temperature, stirring was stopped and the phases were allowed to separate. The lower aqueous phase was removed and discarded (cutting away any interfacial catalyst residues if present) and the acetonitrile phase concentrated to dryness to give typically a light to dark brown solid or dark-coloured gum. Solids were triturated with methanol (20 mL) for 1-2 h, then isolated by filtration, washed once or twice with methanol (4 mL each wash) and dried under vacuum. Oils were purified by flash silica gel chromatography as noted below. All isolated compounds gave 1H NMR data in agreement with published values. Literature data is given for mp values for comparison.
74 %Chromat.	With potassium phosphate monohydrate; 5-(dicyclohexylphosphino)-1-([2.2]paracyclophan-4-yl)-4-pentyl-1H-1,2,3-triazole; palladium diacetate In toluene at 70℃; for 24h;

Yield	Reaction Conditions	Operation in experiment
1: 81% 2: 16 % Chromat.	With indium; dodecane; lithium chloride In N,N-dimethyl-formamide at 100℃; for 3h;
62%	With palladium on activated charcoal; water; sodium hydroxide at 150℃; for 2h; Microwave irradiation; chemoselective reaction;
1: 12% 2: 41%	With [2,2]bipyridinyl; nickel dibromide; zinc In N,N-dimethyl-formamide at 110℃; for 24h;

1: 40% 2: 7.9%	With (C₅H₅)2Zr(OC₄H₈)N(Si(CH₃)3)CH(C₆H₅); tri-tert-butyl phosphine; bis(dibenzylideneacetone)-palladium⁽⁰⁾ In toluene at 80℃; for 16h; Sealed tube; Inert atmosphere;
	With 18-crown-6 ether; zinc In water; N,N-dimethyl-formamide at 20℃;

Yield	Reaction Conditions	Operation in experiment
1: 81% 2: 9%	With sodium carbonate In methanol for 16h; Heating;
1: 81% 2: 9%	With sodium carbonate In 1,2-dimethoxyethane; water for 16h; Heating;

Yield	Reaction Conditions	Operation in experiment
1: 75% 2: 15 % Spectr.	Stage #1: 4-iodoanisol With tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; copper(l) iodide; sodium t-butanolate In toluene for 0.166667h; Stage #2: 2-(hydroxydimethylsilyl)-1H-indole-1-carboxylic acid 1,1-dimethylethyl ester In toluene at 50℃; for 24h;
1: 75% 2: 15 % Spectr.	With copper(l) iodide; sodium t-butanolate In toluene at 50℃; for 24h;

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1.1: CHCl₃ 2.1: 65 percent / Br₂ / CCl₄ / 5 h / 0 °C 3.1: nBuLi / diethyl ether; hexane / 4 h / 0 °C 3.2: B(OiPr)3 / hexane; diethyl ether / 48 h / 20 °C 3.3: 44 percent / aq. HCl / diethyl ether; hexane / 3 h / 20 °C 4.1: 79 percent / aq. K₂CO₃ / Pd(PPh₃)4 / toluene / 26 h / 100 °C
	Multi-step reaction with 4 steps 1.1: CHCl₃ 2.1: 97 percent / Br₂ / CCl₄ 3.1: nBuLi / tetrahydrofuran; hexane / 0.5 h / -80 °C 3.2: 48 percent / I₂ / hexane; tetrahydrofuran / 24 h / 20 °C 4.1: 79 percent / aq. K₂CO₃ / Pd(PPh₃)4 / toluene / 26 h / 100 °C

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 5 steps 1.1: CHCl₃ 2.1: 65 percent / Br₂ / CCl₄ / 5 h / 0 °C 3.1: nBuLi / diethyl ether; hexane / 4 h / 0 °C 3.2: B(OiPr)3 / hexane; diethyl ether / 48 h / 20 °C 3.3: 44 percent / aq. HCl / diethyl ether; hexane / 3 h / 20 °C 4.1: 79 percent / aq. K₂CO₃ / Pd(PPh₃)4 / toluene / 26 h / 100 °C 5.1: BBr₃ / CH₂Cl₂ / 12 h / 20 °C 5.2: 81 percent / water / CH₂Cl₂ / 4 h / 20 °C
	Multi-step reaction with 5 steps 1.1: CHCl₃ 2.1: 97 percent / Br₂ / CCl₄ 3.1: nBuLi / tetrahydrofuran; hexane / 0.5 h / -80 °C 3.2: 48 percent / I₂ / hexane; tetrahydrofuran / 24 h / 20 °C 4.1: 79 percent / aq. K₂CO₃ / Pd(PPh₃)4 / toluene / 26 h / 100 °C 5.1: BBr₃ / CH₂Cl₂ / 12 h / 20 °C 5.2: 81 percent / water / CH₂Cl₂ / 4 h / 20 °C

Yield	Reaction Conditions	Operation in experiment
99%	With potassium phosphate; C₅₀H₆₃Cl₂N₃Pd In ethanol at 80℃; for 4h;
78%	Stage #1: 2-Methoxyphenylboronic acid With potassium phosphate; N,N-diisopropyl 2-dicyclohexylphosphino-5-(3'-nitrophenyl)benzamide; palladium diacetate In tetrahydrofuran at 23℃; for 0.0166667h; Inert atmosphere; Stage #2: 2-Chloroanisole In tetrahydrofuran at 23℃; for 36h; Inert atmosphere;
70%	With palladium diacetate; caesium carbonate; P-phenyl-2,2,6,6-tetramethyl-phosphorinan-4-ol In toluene at 110℃; for 48h; Inert atmosphere;

61%	With 2-[2-(diisobutylphosphinyl)ethyl]pyridine; palladium diacetate; caesium carbonate In toluene at 110℃; for 24h; Inert atmosphere;
	With 5-diisopropylphosphanyl-4⁽²⁴⁾,6⁽¹⁰⁾,12⁽¹⁶⁾,18⁽²²⁾-tetramethylenedioxy-2,8,14,20-tetrapentylresorcin[4]arene; palladium diacetate; sodium hydride In decane; N,N-dimethyl-formamide at 100℃; for 8h; Schlenk technique; Inert atmosphere;
	With 5-diisopropylphosphanyl-{4⁽²⁴⁾,6⁽¹⁰⁾,12⁽¹⁶⁾,18⁽²²⁾-tetramethylenedioxy-2,8,14,20-tetrapentylresorcin[4]arene}; palladium diacetate; sodium hydride In 1,4-dioxane; decane; mineral oil at 100℃; for 8h; Schlenk technique; Inert atmosphere;
	With trans-dibromo-{5-[3-(2,4,6-trimethylphenyl)-imidazol-2-yliden-1-yl]-4⁽²⁴⁾,6⁽¹⁰⁾,12⁽¹⁶⁾,18⁽²²⁾-tetramethylenedioxy-2,8,14,20-tetrapentylresorcin[4]arene}pyridinepalladium(II); sodium hydride In 1,4-dioxane; mineral oil at 75℃; for 8h; Inert atmosphere; Schlenk technique;
	With tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; 5-(2-dicyclohexylphosphanyl phenyl)-25,26,27,28-tetrapropyloxycalix[4]arene; potassium <i>tert</i>-butylate In 1,4-dioxane; decane at 100℃; for 16h; Inert atmosphere; Schlenk technique;
	With 5-(2-dicyclohexylphosphinophenyl)-4⁽²⁴⁾,6⁽¹⁰⁾,12⁽¹⁶⁾,18⁽²²⁾-tetramethylenedioxy-2,8,14,20-tetrapentylresorcin[4]arene; potassium <i>tert</i>-butylate; palladium diacetate In 1,4-dioxane at 100℃; for 16h; Schlenk technique; Inert atmosphere;