96% |
With potassium permanganate; copper(II) sulphate for 48h; other reagent, reaction time; |
|
96% |
With NaBrO3; sodium hydrogen sulphite In water monomer at 20℃; for 16.25h; |
|
96% |
With water monomer; potassium bromide at 20℃; for 2h; |
|
95% |
With potassium permanganate; copper(II) sulphate at 20℃; for 0.0833333h; |
|
95% |
With NaBrO3; Rexyn 101 H resin at 20℃; for 2.5h; |
|
94% |
With potassium permanganate; Rexyn 101 H ion exchange resin In dichloromethane for 6.3h; Heating; |
|
94% |
With water monomer; 4-acetylamino-2,2,6,6-tetramethylpiperidine-1-oxoammonium tetrafluoroborate In acetonitrile at 20℃; for 8h; |
|
94% |
With N-hydroxyphthalimide; oxygen In acetonitrile at 80℃; for 12h; |
|
91% |
With aluminum(III) oxide; potassium permanganate; water monomer In 1,2-dichloro-ethane for 66h; Ambient temperature; |
|
91% |
With manganese(IV) oxide at 105℃; for 0.0416667 - 0.0666667h; Inert atmosphere; Microwave irradiation; |
|
90% |
With potassium permanganate; iron(III) chloride In acetone at -78℃; for 1h; |
|
90% |
With potassium permanganate; Montmorillonite K10 at 23℃; for 20h; |
|
90% |
With cerium(III) sulphate; barium bromate In water monomer; acetonitrile for 2h; Heating; |
|
90% |
With tert.-butylhydroperoxide; potassium iodide In water monomer; acetonitrile at 20℃; for 7h; |
|
90% |
With oxygen In water monomer for 3.5h; Irradiation; |
|
88% |
With tert.-butylhydroperoxide; C24H18N6O3*Cu(1+)*I(1-) In water monomer at 20℃; for 4h; |
|
86% |
With carbon monoxide; oxygen; copper chloride (II); palladium (II) chloride In water monomer; acetone at 25℃; for 48h; other benzylic ethers, tosylamides and 9,10-dihydroanthracene; other Pd and Cu salts; var. solvents, pressure and reaction time; |
|
86% |
With carbon monoxide; oxygen; copper chloride (II); palladium (II) chloride In water monomer; acetone for 48h; |
|
86% |
With tert.-butylhydroperoxide; 2C36H20N2O8(4-)*5Co(2+)*2HO(1-)*4H2O*6C3H7NO In water monomer at 20℃; for 9h; Sonication; regioselective reaction; |
|
85% |
With pyridinium chlorochromate In dichloromethane at 60 - 70℃; for 24h; |
|
85% |
With NaBrO3; sulfuric acid; mesoporous silica at 20℃; for 4.5h; |
|
84% |
With 2-Nitrobenzenesulfonyl chloride In acetonitrile at -25℃; for 4h; |
|
84% |
With NaBrO3; 1-butyl-3-methyl-1H-imidazol-3-ium bromide at 70℃; for 15h; |
|
81% |
With manganese(IV) oxide; potassium permanganate In dichloromethane at 20℃; for 16h; |
|
81% |
With potassium permanganate at 20℃; for 4h; |
|
81% |
With tert.-butylhydroperoxide; triethylamine; 1,3-bis(2,6-diisopropylphenyl)imidazolinium chloride In water monomer; acetonitrile at 80℃; for 15h; |
|
80% |
With sodium 2-iodobenzenesulfonate; Oxone; tetrabutylammonium hydrogensulfate In acetonitrile at 60℃; for 5h; |
|
80% |
With oxygen In water monomer at 20℃; for 12h; Schlenk technique; Irradiation; |
|
78% |
With potassium carbonate; 1-tert-butylperoxy-1,2-benziodoxol-3(1H)-one In benzene for 23h; Ambient temperature; |
|
75% |
With sodium chlorine monoxide; racemic (salen)Mn(III) In dichloromethane at 0℃; for 4h; |
|
75% |
With sodium hypochlorite In 1,1,1-trichloroethane; water monomer at 55 - 65℃; for 2.5h; |
|
74% |
With potassium peroxymonosulfate; cobalt(II) perchlorate In water monomer; acetonitrile at 25℃; for 3h; Sealed tube; |
2. Experimental details and characterization datafor products 2
General procedure: A mixture of 1 (0.2 mmol), Co(ClO4)2 (0.02 mmol), Oxone (1.2 mmol), CH3CN (2 mL) and H2O (2 mL) was stirred in a sealed tube at 25 °C for 3 h. After the reaction was completed (as monitored by TLC), the mixture was placed and allowed to separate into layers. Then the upper organic layer was separated, dried with anhydrous Na2SO4, and concentrated under reduced pressure. The resulting residue was purified by preparative TLC (petroleum ether/ethyl acetate = 10:1, v/v) to yield 2. |
71% |
With hydrogenchloride; tetrakis(tetrabutylammonium)decatungstate(VI); oxygen In water monomer; acetonitrile at 20℃; for 0.75h; Flow reactor; Irradiation; |
|
71% |
With cercosporin; oxygen; potassium bromide In methanol at 20℃; Irradiation; Schlenk technique; Green chemistry; chemoselective reaction; |
|
71% |
With oxygen In water monomer at 20℃; for 24h; Irradiation; Green chemistry; |
|
71% |
With alpha-angelicalactone; dmap; oxygen In 2-methyltetrahydrofuran at 80℃; for 24h; Inert atmosphere; |
|
70% |
With tert.-butylhydroperoxide; copper(II) dichloride dihydrate; tetra-n-butyl-ammonium chloride; anhydrous sodium carbonate; 2,2'-biquinoline-4,4'-dicarboxylic acid dipotassium salt In water monomer at 20℃; for 17h; Green chemistry; |
|
70% |
With oxygen; 2K(1+)*2Na(1+)*5H(1+)*36H2O*3Fe(3+)*2(P2W15Nb3O62)(9-) In acetone at 20℃; for 24h; Irradiation; |
|
67% |
With copper(II) dichloride dihydrate; oxygen; hydroquinone at 30℃; for 18h; Sealed tube; Irradiation; Green chemistry; |
|
65% |
With chromium (VI) oxide In toluene for 1.16667h; Heating; microwave-irradiation; |
|
65% |
With pyridine; tert.-butylhydroperoxide; air; K(1+)*AuCl4(1-)*0.5H2O=K[AuCl4]*0.5H2O In decane at 90℃; |
|
56% |
With tert.-butylhydroperoxide In acetonitrile at 80℃; for 2h; |
|
52% |
With 1,1'-bis(diphenylphosphanyl)ferrocene; oxygen; diphenyldisulfane In 1,4-dioxane at 80℃; for 15h; Schlenk technique; regioselective reaction; |
|
50% |
With tert.-butylhydroperoxide; dirhodium(II) tetra-2-(methanesulfonylimino)pyrrolidine In methanol; water monomer at 20℃; for 20h; |
|
45% |
With pyridine; tert.-butylhydroperoxide; iron(III) chloride at 82℃; for 24h; |
|
17% |
With iron(II) trifluoromethanesulfonate; 2-((4R,5R)-1-((4-(tert-butyl)phenyl)sulfonyl)-4,5-diphenylimidazolidin-2-yl)-6-((4R,5R)-1-((4-(tert-butyl)phenyl)sulfonyl)-4,5-diphenylimidazolidin-2-yl)pyridine; oxygen at 60℃; for 16h; Green chemistry; regioselective reaction; |
|
|
With oxygen; titanium(IV) dioxide In acetonitrile Bi(OAc)3 filter; |
|
61 % Spectr. |
With oxygen; dibenzoyl In benzene at 5 - 10℃; for 3h; Irradiation; |
|
59 % Chromat. |
With potassium permanganate; benzyl-triethyl-ammonium chloride In dichloromethane for 1.5h; Heating; |
|
93 % Spectr. |
With potassium permanganate; copper(II) sulphate In dichloromethane at 20℃; for 2h; ultrasonic irradiation; |
|
62 % Chromat. |
With laccase of Trametes villosa; Poliporus pinsitus; oxygen; benzotriazol-1-ol In acetonitrile at 20℃; for 24h; |
|
94 %Chromat. |
With potassium peroxomonosulfate; water monomer; potassium bromide In acetonitrile at 45℃; |
General procedure
General procedure: To a solution of aromatic compound 1a-q (1 mmol) in CH3CN (6 mL) and H2O (0.5 mL) were added KBr (0.5 mmol) and Oxone (2.2 mmol), and the mixture was stirred at 45°C. After completion (monitored by TLC), the reaction mixture was filtered and the solvent was evaporated under reduced pressure. The residue was dissolved in ethyl acetate, washed with saturated aqueous Na2S2O3 and brine, dried over anhydrous Na2SO4. Removal of the solvent under vacuum afforded the crude product, which was purified by column chromatography using hexane/ethyl acetate as eluent (20 - 80 : 1). |
|
Multi-step reaction with 2 steps
1: 2-((4R,5R)-1-((4-(tert-butyl)phenyl)sulfonyl)-4,5-diphenylimidazolidin-2-yl)-6-((4R,5R)-1-((4-(tert-butyl)phenyl)sulfonyl)-4,5-diphenylimidazolidin-2-yl)pyridine; oxygen-<SUP>18</SUP>O<SUB>2</SUB>; iron(II) trifluoromethanesulfonate; oxygen / benzene / 16 h / 60 °C / 760.05 Torr / Green chemistry
2: [Fe(2-((4R,5R)-1-((4-(tert-butyl)phenyl)sulfonyl)-4,5-diphenylimidazolidin-2-yl)-6-((4R,5R)-1-((4-(tert-butyl)phenyl)sulfonyl)-4,5-diphenylimidazolidin-2-yl)pyridine)(THF)(OTf)2] / benzene / 45 °C / Schlenk technique; Inert atmosphere; Green chemistry |
|
|
Multi-step reaction with 2 steps
1: 2-((4R,5R)-1-((4-(tert-butyl)phenyl)sulfonyl)-4,5-diphenylimidazolidin-2-yl)-6-((4R,5R)-1-((4-(tert-butyl)phenyl)sulfonyl)-4,5-diphenylimidazolidin-2-yl)pyridine; iron(II) trifluoromethanesulfonate; oxygen / benzene / 42 °C / 760.05 Torr / Schlenk technique; Inert atmosphere; Green chemistry
2: [Fe(2-((4R,5R)-1-((4-(tert-butyl)phenyl)sulfonyl)-4,5-diphenylimidazolidin-2-yl)-6-((4R,5R)-1-((4-(tert-butyl)phenyl)sulfonyl)-4,5-diphenylimidazolidin-2-yl)pyridine)(THF)(OTf)2] / benzene / 45 °C / Schlenk technique; Inert atmosphere; Green chemistry |
|
90 %Chromat. |
With porous chitosan-manganese dioxide nanohybrid; air In para-xylene at 100℃; for 7h; Green chemistry; |
|
70 %Chromat. |
With sodium (meta)periodate; [(Npy^CNHC)RuII(2,2'-bipyridine)(CH3CN)2](PF6)(CF3SO3) In water monomer; acetonitrile at 70℃; for 4h; |
|
26.2%Chromat. |
With cerium oxide gold; oxygen In tetrahydrofuran at 100℃; for 6h; Autoclave; |
|
98 %Spectr. |
With Peroxyacetic acid; C20H21N4O2Pd(1+)*F6P(1-)*C2H3N; acetic acid In acetonitrile at 60℃; for 24h; |
|
94 %Chromat. |
With oxygen; Ti8(μ2-O)8[Cu(μ2-O)2(μ2-OH)]2(1,4-benzenedicarboxylato)6Li2; 2-Methylpropanal In 1,2-dichloro-ethane at 20℃; for 48h; Sealed tube; Inert atmosphere; |
|
> 99 %Chromat. |
With tert.-butylhydroperoxide; 2Cu(2+)*C33H17NO8(4-)*H2O*3C3H7NO In acetonitrile at 65℃; for 4h; |
|