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inquiry2,2'-Bithiophene
4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane
5,5'-di(4,4,5,5-tetramethyl-1,3,2-dioxaborolane-2-yl)-2,2'-bithiophene
Conditions | Yield |
---|---|
With iridium-bipyridine periodic mesoporous organosilica In cyclohexane at 80℃; for 12h; Inert atmosphere; Schlenk technique; regioselective reaction; | 99% |
2,3-dimethyl-2,3-butane diol
2,2'-Bithiophene
boron trichloride
5,5'-di(4,4,5,5-tetramethyl-1,3,2-dioxaborolane-2-yl)-2,2'-bithiophene
Conditions | Yield |
---|---|
With AlCl3; Me2NTol In dichloromethane 1:1 mixt. of BCl3 and AlCl, pinacol (2.3-3.0 equiv.) and lutidine (15 equiv.) for 18 h; | 83% |
2,3-dimethyl-2,3-butane diol
2,2'-Bithiophene
5,5'-di(4,4,5,5-tetramethyl-1,3,2-dioxaborolane-2-yl)-2,2'-bithiophene
Conditions | Yield |
---|---|
Stage #1: 2,2'-Bithiophene With aluminum (III) chloride; boron trichloride; Dimethyl-p-toluidine In dichloromethane for 24h; Stage #2: 2,3-dimethyl-2,3-butane diol With triethylamine In dichloromethane at 20℃; for 0.5h; | 83% |
2,2'-Bithiophene
bis(pinacol)diborane
5,5'-di(4,4,5,5-tetramethyl-1,3,2-dioxaborolane-2-yl)-2,2'-bithiophene
Conditions | Yield |
---|---|
With (1,5-cyclooctadiene)(methoxy)iridium(I) dimer; 4,4'-di-tert-butyl-2,2'-bipyridine In hexane at 50℃; for 0.25h; | 82% |
2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
2,2'-Bithiophene
5,5'-di(4,4,5,5-tetramethyl-1,3,2-dioxaborolane-2-yl)-2,2'-bithiophene
Conditions | Yield |
---|---|
Stage #1: 2,2'-Bithiophene With n-butyllithium In tetrahydrofuran; hexane at -78 - 20℃; for 2h; Inert atmosphere; Stage #2: 2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane In tetrahydrofuran; hexane at -78 - 20℃; Inert atmosphere; | 72% |
Stage #1: 2,2'-Bithiophene With n-butyllithium; N,N,N,N,-tetramethylethylenediamine In hexane for 1.41667h; Stage #2: 2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane In hexane at -78 - 20℃; for 16h; | 57% |
Stage #1: 2,2'-Bithiophene With n-butyllithium; N,N,N,N,-tetramethylethylenediamine In tetrahydrofuran; hexane for 0.5h; Heating; Stage #2: 2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane In tetrahydrofuran; hexane at -78 - -20℃; for 19h; | 53% |
2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
4,4,5,5-tetramethyl-2-(5-(trimethylstannyl)thiophen-2-yl)-1,3,2-dioxaborolane
5,5'-di(4,4,5,5-tetramethyl-1,3,2-dioxaborolane-2-yl)-2,2'-bithiophene
Conditions | Yield |
---|---|
With tetrakis(triphenylphosphine) palladium(0) In toluene at 100℃; for 4h; Microwave irradiation; | 52% |
2,3-dimethyl-2,3-butane diol
2,2'-Bithiophene
A
2-([2,2'-bithiophen]-5-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
B
5,5'-di(4,4,5,5-tetramethyl-1,3,2-dioxaborolane-2-yl)-2,2'-bithiophene
Conditions | Yield |
---|---|
Stage #1: 2,2'-Bithiophene With n-butyllithium In tetrahydrofuran at -78 - 20℃; for 4h; Stage #2: With Trimethyl borate In tetrahydrofuran for 2h; Stage #3: 2,3-dimethyl-2,3-butane diol In tetrahydrofuran for 12h; Further stages.; | A 44% B 0.35 g |
2,3-dimethyl-2,3-butane diol
5,5′-bis(dichloroboryl)-2,2′-bithiophene
5,5'-di(4,4,5,5-tetramethyl-1,3,2-dioxaborolane-2-yl)-2,2'-bithiophene
Conditions | Yield |
---|---|
With triethylamine at 20℃; for 0.5h; Inert atmosphere; | 44 mg |
With triethylamine at 0 - 20℃; for 1h; Inert atmosphere; |
2,2'-Bithiophene
5,5'-di(4,4,5,5-tetramethyl-1,3,2-dioxaborolane-2-yl)-2,2'-bithiophene
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: aluminum (III) chloride; boron trichloride; Dimethyl-p-toluidine / dichloromethane / 24 h / Inert atmosphere 2: triethylamine / 0.5 h / 20 °C / Inert atmosphere View Scheme | |
Multi-step reaction with 2 steps 1: aluminum (III) chloride; BCl3*C9H13N / dichloromethane / 24 h / 20 °C / Schlenk technique; Inert atmosphere 2: triethylamine / 1 h / 0 - 20 °C / Inert atmosphere View Scheme |
bromostyrene
4,4,5,5-tetramethyl-2-(5-(trimethylstannyl)thiophen-2-yl)-1,3,2-dioxaborolane
B
5,5'-di(4,4,5,5-tetramethyl-1,3,2-dioxaborolane-2-yl)-2,2'-bithiophene
Conditions | Yield |
---|---|
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride In N,N-dimethyl-formamide at 60℃; for 16h; |
bromostyrene
4,4,5,5-tetramethyl-2-(5-(trimethylstannyl)thiophen-2-yl)-1,3,2-dioxaborolane
C
5,5'-di(4,4,5,5-tetramethyl-1,3,2-dioxaborolane-2-yl)-2,2'-bithiophene
Conditions | Yield |
---|---|
With tetrakis(triphenylphosphine) palladium(0) In toluene at 60℃; for 17h; |
bromostyrene
4,4,5,5-tetramethyl-2-(5-(trimethylstannyl)thiophen-2-yl)-1,3,2-dioxaborolane
C
1,4-diphenyl-1,3-butadiene
D
5,5'-di(4,4,5,5-tetramethyl-1,3,2-dioxaborolane-2-yl)-2,2'-bithiophene
Conditions | Yield |
---|---|
With tetrakis(triphenylphosphine) palladium(0) In 1,4-dioxane; toluene at 65℃; for 26h; Reagent/catalyst; Solvent; Temperature; |
2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
5,5'-di(4,4,5,5-tetramethyl-1,3,2-dioxaborolane-2-yl)-2,2'-bithiophene
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1.1: methyllithium / diethyl ether; tetrahydrofuran / 2 h / -100 °C 1.2: 13 h / -100 - 20 °C 2.1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / N,N-dimethyl-formamide / 16 h / 60 °C View Scheme | |
Multi-step reaction with 2 steps 1.1: methyllithium / diethyl ether; tetrahydrofuran / 2 h / -100 °C 1.2: 13 h / -100 - 20 °C 2.1: tetrakis(triphenylphosphine) palladium(0) / toluene / 4 h / 100 °C / Microwave irradiation View Scheme |
2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
B
5,5'-di(4,4,5,5-tetramethyl-1,3,2-dioxaborolane-2-yl)-2,2'-bithiophene
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1.1: methyllithium / diethyl ether; tetrahydrofuran / 2 h / -100 °C 1.2: 13 h / -100 - 20 °C 2.1: tetrakis(triphenylphosphine) palladium(0) / toluene / 17 h / 60 °C View Scheme | |
Multi-step reaction with 2 steps 1.1: methyllithium / diethyl ether; tetrahydrofuran / 2 h / -100 °C 1.2: 13 h / -100 - 20 °C 2.1: tetrakis(triphenylphosphine) palladium(0) / toluene; 1,4-dioxane / 26 h / 65 °C View Scheme |
Triisopropyl borate
5,5'-di(4,4,5,5-tetramethyl-1,3,2-dioxaborolane-2-yl)-2,2'-bithiophene
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 2,3-dimethyl-2,3-butane diol / hexane / 90 °C 2: tetrakis(triphenylphosphine) palladium(0) / toluene / 4 h / 100 °C / Microwave irradiation View Scheme | |
Multi-step reaction with 3 steps 1.1: 2,3-dimethyl-2,3-butane diol / hexane / 90 °C 2.1: methyllithium / diethyl ether; tetrahydrofuran / 2 h / -100 °C 2.2: 13 h / -100 - 20 °C 3.1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / N,N-dimethyl-formamide / 16 h / 60 °C View Scheme | |
Multi-step reaction with 3 steps 1.1: 2,3-dimethyl-2,3-butane diol / hexane / 90 °C 2.1: methyllithium / diethyl ether; tetrahydrofuran / 2 h / -100 °C 2.2: 13 h / -100 - 20 °C 3.1: tetrakis(triphenylphosphine) palladium(0) / toluene / 4 h / 100 °C / Microwave irradiation View Scheme |
Triisopropyl borate
B
5,5'-di(4,4,5,5-tetramethyl-1,3,2-dioxaborolane-2-yl)-2,2'-bithiophene
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1.1: 2,3-dimethyl-2,3-butane diol / hexane / 90 °C 2.1: methyllithium / diethyl ether; tetrahydrofuran / 2 h / -100 °C 2.2: 13 h / -100 - 20 °C 3.1: tetrakis(triphenylphosphine) palladium(0) / toluene / 17 h / 60 °C View Scheme | |
Multi-step reaction with 3 steps 1.1: 2,3-dimethyl-2,3-butane diol / hexane / 90 °C 2.1: methyllithium / diethyl ether; tetrahydrofuran / 2 h / -100 °C 2.2: 13 h / -100 - 20 °C 3.1: tetrakis(triphenylphosphine) palladium(0) / toluene; 1,4-dioxane / 26 h / 65 °C View Scheme |
5-bromo-2-hexylisoindoline-1,3-dione
5,5'-di(4,4,5,5-tetramethyl-1,3,2-dioxaborolane-2-yl)-2,2'-bithiophene
5,5'-(2,2'-bithiophene-5,5'-diyl)bis(2-hexylphthalimide)
Conditions | Yield |
---|---|
With potassium carbonate In N,N-dimethyl-formamide at 90℃; for 0.5h; Reagent/catalyst; Suzuki Coupling; Microwave irradiation; Inert atmosphere; | 100% |
5,5'-di(4,4,5,5-tetramethyl-1,3,2-dioxaborolane-2-yl)-2,2'-bithiophene
Conditions | Yield |
---|---|
With [1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene](3-chloropyridyl)palladium(ll) dichloride; potassium carbonate In methanol; toluene at 90℃; for 24h; Inert atmosphere; Schlenk technique; | 97% |
(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy)-4-iodobenzene
5,5'-di(4,4,5,5-tetramethyl-1,3,2-dioxaborolane-2-yl)-2,2'-bithiophene
5,5'-bis-(4-[2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy]phenyl)-[2,2']-bithiophene
Conditions | Yield |
---|---|
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; silver(l) oxide In 1,4-dioxane at 70℃; Suzuki-Miyaura coupling; Inert atmosphere; | 91% |
(S)-4-iodo-1-(6-(2-tert-butoxycarbonylamino-3-phenylpropanoyloxy)hexyloxy)benzene
5,5'-di(4,4,5,5-tetramethyl-1,3,2-dioxaborolane-2-yl)-2,2'-bithiophene
(S,S)-5,5'-bis-(4-(6-(2-tert-butoxycarbonylamino-3-phenylpropanoyloxy)hexyloxy)phenyl)-[2,2']-bithiophene
Conditions | Yield |
---|---|
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; silver(l) oxide In 1,4-dioxane at 70℃; Suzuki-Miyaura coupling; Inert atmosphere; | 91% |
2-(thiophen-2-yl)vinyl bromide
5,5'-di(4,4,5,5-tetramethyl-1,3,2-dioxaborolane-2-yl)-2,2'-bithiophene
Conditions | Yield |
---|---|
With sodium hydroxide; bis(dibenzylideneacetone)-palladium(0); tri tert-butylphosphoniumtetrafluoroborate In tetrahydrofuran; water at 30℃; for 20h; | 89% |
methyl 2-(2-bromothiophene-3-yl)acetate
5,5'-di(4,4,5,5-tetramethyl-1,3,2-dioxaborolane-2-yl)-2,2'-bithiophene
C22H18O4S4
Conditions | Yield |
---|---|
With [1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene](3-chloropyridyl)palladium(II) dichloride; potassium carbonate In methanol; toluene at 70℃; for 0.25h; Suzuki coupling; | 85% |
5,5'-di(4,4,5,5-tetramethyl-1,3,2-dioxaborolane-2-yl)-2,2'-bithiophene
Conditions | Yield |
---|---|
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In toluene for 24h; Reflux; | 85% |
5,5'-di(4,4,5,5-tetramethyl-1,3,2-dioxaborolane-2-yl)-2,2'-bithiophene
Conditions | Yield |
---|---|
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In toluene for 24h; Reflux; | 80% |
C25H22BBr
5,5'-di(4,4,5,5-tetramethyl-1,3,2-dioxaborolane-2-yl)-2,2'-bithiophene
C58H48B2S2
Conditions | Yield |
---|---|
With tris(dibenzylideneacetone)dipalladium(0) chloroform complex; potassium phosphate; XPhos In tetrahydrofuran; water at 20℃; for 3.5h; Suzuki-Miyaura Coupling; Reflux; Inert atmosphere; | 77% |
5,5'-di(4,4,5,5-tetramethyl-1,3,2-dioxaborolane-2-yl)-2,2'-bithiophene
Conditions | Yield |
---|---|
With bis-triphenylphosphine-palladium(II) chloride; tetramethylammonium bromide; sodium carbonate at 80℃; for 24h; Suzuki Coupling; Inert atmosphere; | 76% |
5,5'-di(4,4,5,5-tetramethyl-1,3,2-dioxaborolane-2-yl)-2,2'-bithiophene
Conditions | Yield |
---|---|
With bis-triphenylphosphine-palladium(II) chloride; tetramethylammonium bromide; sodium carbonate at 80℃; for 24h; Suzuki Coupling; Inert atmosphere; | 76% |
2-[2-(2-(2-(4-iodophenoxy)ethoxy)ethoxy)ethoxy]ethanol
5,5'-di(4,4,5,5-tetramethyl-1,3,2-dioxaborolane-2-yl)-2,2'-bithiophene
C36H46O10S2
Conditions | Yield |
---|---|
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In N,N-dimethyl-formamide at 50℃; for 16h; Inert atmosphere; | 75% |
C35H43BrN2S
5,5'-di(4,4,5,5-tetramethyl-1,3,2-dioxaborolane-2-yl)-2,2'-bithiophene
5,5'-bis(7-(9,9-dioctyl-9H-fluoren-2-yl)-2,1,3-benzothiadiazol-4-yl)-2,2'-bithiophene
Conditions | Yield |
---|---|
With tetrakis(triphenylphosphine) palladium(0); Aliquat 336; potassium carbonate In water; toluene for 24h; Suzuki Coupling; Inert atmosphere; Reflux; | 75% |
5,5'-di(4,4,5,5-tetramethyl-1,3,2-dioxaborolane-2-yl)-2,2'-bithiophene
Conditions | Yield |
---|---|
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In toluene for 12h; Reflux; | 75% |
(triphenylphosphine)gold(I) chloride
5,5'-di(4,4,5,5-tetramethyl-1,3,2-dioxaborolane-2-yl)-2,2'-bithiophene
5,5'-bis[(triphenylphosphine)gold(I)]-2,2'-bithiophene
Conditions | Yield |
---|---|
With cesium carbonate In isopropyl alcohol addn. of PPh3AuCl, 2,2'-bithiophene-5,5'-diboronic acid bis(pinacol ester) and Cs2CO3 under Ar, suspending in 2-propanol, stirring under Ar at 40°C for 24 h; removal of 2-propanol by rotary evapn., extn. into dry CH2Cl2, filtration, removal of CH2Cl2 by rotary evapn., trituration with pentane, filtration; elem. anal.; | 69% |
bis-[(trifluoroacetoxy)iodo]benzene
5,5'-di(4,4,5,5-tetramethyl-1,3,2-dioxaborolane-2-yl)-2,2'-bithiophene
phenyl(5'-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-[2,2'-bithiophen]-5-yl)iodonium trifluoroacetate
Conditions | Yield |
---|---|
With acetic acid In dichloromethane at 20℃; for 6h; regioselective reaction; | 68% |
5,5'-di(4,4,5,5-tetramethyl-1,3,2-dioxaborolane-2-yl)-2,2'-bithiophene
Conditions | Yield |
---|---|
With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium carbonate In ethanol; water; toluene for 18h; Inert atmosphere; Reflux; | 60% |
2-bromodithieno[3,2-b:2',3'-d]phosphole oxide
5,5'-di(4,4,5,5-tetramethyl-1,3,2-dioxaborolane-2-yl)-2,2'-bithiophene
C36H20O2P2S6
Conditions | Yield |
---|---|
With tetrakis(triphenylphosphine) palladium(0); cesium fluoride In tetrahydrofuran at 70℃; for 72h; Suzuki-Miyaura crosscoupling; Inert atmosphere; | 58% |
N,N’-bis(rac-2-ethylhexyl)-6-bromoisoindigo
5,5'-di(4,4,5,5-tetramethyl-1,3,2-dioxaborolane-2-yl)-2,2'-bithiophene
C72H86N4O4S2
Conditions | Yield |
---|---|
With tris-(dibenzylideneacetone)dipalladium(0); tetraethylammonium hydroxide; tris-(o-tolyl)phosphine In toluene at 85℃; Suzuki coupling; Inert atmosphere; | 57% |
5,5'-di(4,4,5,5-tetramethyl-1,3,2-dioxaborolane-2-yl)-2,2'-bithiophene
methyl 2-(2-bromothiophen-3-yl)ethan-1-ol
C20H18O2S4
Conditions | Yield |
---|---|
With potassium fluoride; [1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene](3-chloropyridyl)palladium(ll) dichloride In methanol; toluene at 55℃; for 0.75h; Suzuki Coupling; Inert atmosphere; | 56% |
With potassium fluoride; [1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene](3-chloropyridyl)palladium(ll) dichloride In methanol; toluene at 55℃; for 0.75h; Suzuki Coupling; Inert atmosphere; | 56% |
5,5'-di(4,4,5,5-tetramethyl-1,3,2-dioxaborolane-2-yl)-2,2'-bithiophene
6-bromo-2,3-dihydrothieno[3,2-b][1,4]oxathiine
Conditions | Yield |
---|---|
With cesium fluoride; tetrakis(triphenylphosphine) palladium(0) In 1,4-dioxane for 48h; Suzuki coupling; Heating; | 47% |
4-bromo-2,6-dimethoxyphenol
5,5'-di(4,4,5,5-tetramethyl-1,3,2-dioxaborolane-2-yl)-2,2'-bithiophene
Conditions | Yield |
---|---|
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In water; toluene at 130℃; for 0.7h; Suzuki Coupling; Microwave irradiation; | A 7% B 46% |
3,7-dibromo-5,5-di-n-octyl-dibenzo[b,d]silole
5,5'-di(4,4,5,5-tetramethyl-1,3,2-dioxaborolane-2-yl)-2,2'-bithiophene
Conditions | Yield |
---|---|
With Aliquat 336; sodium carbonate; tetrakis(triphenylphosphine) palladium(0) In water; toluene for 48h; Suzuki coupling; Heating; | 45% |
3,7-dibromo-5,5-di-n-octyl-dibenzo[b,d]silole
5,5'-di(4,4,5,5-tetramethyl-1,3,2-dioxaborolane-2-yl)-2,2'-bithiophene
poly(9,9-di-n-octyldibenzosilole-alt-bithiophene), Mw (GPC) = 127 KD, PDI = 3.7; prepared by Suzuki coupling reaction; monomer(s): 2,7-dibromo-9,9'-di-n-octyldibenzosilole; 2,5'-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)bithiophene
Conditions | Yield |
---|---|
With Aliquat 336; sodium carbonate; tetrakis(triphenylphosphine) palladium(0) In toluene for 48h; Suzuki coupling reaction; Heating; | 45% |
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