Dayangchem's R&D center can offer custom synthesis according to the contract research and development services for the fine chemicals, pharmaceutical, biotechnique and some of the other chemicals. DayangChem can provide different quantities
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inquiryProducts Name: 4,4,5,5-tetramethyl-1,3,2-dioxa-borolane CAS NO.: 25015-63-8 Molecular formula: C6H13BO2 Molecular weight: 127.9772 Appearance:White powder Storage:S
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inquiryPinacolborane CAS:25015-63-8 Qingdao Belugas Import and Export Co., Ltd. is a scientific and technological company integrating research and development, production and trade of chemical intermediates, specializing in high quality organic intermedia
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inquiryChina cheap price 4,4,5,5-tetramethyl-1,3,2-dioxa-borolaneAppearance:Colorless transparent liquid Storage:Store in dry, dark and ventilated place. Package:according to customers' requirements Application:chemical research Transportation:By air(EMS or
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Product Name: Pinacolborane Synonyms: Pinacolatoborane;TetraMethyl-1,3,2-dioxab;Pinacolborane, 97%, stabilized;4,4,5,5-TetraMethyl-1,3,2-dioxaborolane 97%;4,4,5,5-TetraMethyl-1,3,2-dioxaborolane solution 1.0 M in THF;Pinacolborane (4,4,5,5-Tetr
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2-phenylpyridine
bis(pinacol)diborane
A
2-(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)pyridine
B
4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane
Conditions | Yield |
---|---|
With catalyst: [Rh(OH)((CHCHC2H4)2)]2/Silica-SMAP In tetrahydrofuran for 1 h at room temp.; | A 98% B n/a |
benzene-d6
A
deutero-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
B
4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane
Conditions | Yield |
---|---|
In benzene-d6 (N2); heated at 55°C for 90 min; not isolated, detected by NMR; | A n/a B n/a C 95% |
Ethyl tert-butyl ether
bis(pinacol)diborane
A
4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane
B
2-(2-tert-butoxyethyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
Conditions | Yield |
---|---|
(η5-pentamethylcyclopentadienyl)(η6-hexamethylbenzene)rhodium(I) In neat (no solvent) for 24 h at 150°C; | A n/a B 91% |
With carbon monoxide; pentamethylcyclopentadienyltricarbonylrhenium In pentane at 25℃; under 1520 Torr; for 46h; Borylation; Irradiation; | A 26 % Spectr. B 75% |
With carbon monoxide; pentamethylcyclopentadienyltricarbonylrhenium In neat (no solvent) Irradiation (UV/VIS); 25°C, 46 h; chromy. (SiO2; pentane or pentane/Et2O); | A n/a B 75% |
(η5-pentamethylcyclopentadienyl)(η6-hexamethylbenzene)rhodium(I) In cyclohexane for 24 h at 150°C; | A n/a B 48% |
bis[dichloro(pentamethylcyclopentadienyl)ruthenium(III)] In octane 150°C, 24 h; |
2,3-dimethyl-2,3-butane diol
dichloroborane
4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane
Conditions | Yield |
---|---|
With triethylamine In 1,4-dioxane at 0 - 20℃; for 12h; pH=12; Solvent; pH-value; Reagent/catalyst; Concentration; Inert atmosphere; | 91% |
2-(piperidin-1-yl)pyridine
bis(pinacol)diborane
A
2-(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)piperidin-1-yl)pyridine
B
4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane
Conditions | Yield |
---|---|
With methoxy(cyclooctadiene)rhodium(I) dimer In tetrahydrofuran at 80℃; for 15h; Inert atmosphere; Glovebox; | A 89% B n/a |
With methoxy(cyclooctadiene)rhodium(I) dimer In hexane at 80℃; for 12h; Inert atmosphere; regioselective reaction; |
2,3-dimethyl-2,3-butane diol
dimethylsulfide borane complex
4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane
Conditions | Yield |
---|---|
With 2,6-di-tert-butyl-4-methyl-phenol In dichloromethane at -10 - 0℃; Inert atmosphere; | 88.8% |
In dichloromethane at 0 - 20℃; for 13h; Inert atmosphere; | 68% |
In dichloromethane at 0 - 20℃; for 13h; Inert atmosphere; | 68% |
octane
bis(pinacol)diborane
A
4,4,5,5-tetramethyl-2-octyl-[1,3,2]dioxaborolane
B
4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane
Conditions | Yield |
---|---|
With catalyst: [Ir((CHCHC2H4)2)OCH3]2/(CH3)4C12H4N2 In neat (no solvent) for 24 h at 120°C; | A 88% B n/a |
bis[dichloro(pentamethylcyclopentadienyl)ruthenium(III)] In octane 150°C, 48 h; | A 75% B n/a |
[bis(2-methylallyl)cycloocta-1,5-diene]ruthenium(II) In octane 150°C, 48 h; |
tetrahydrofuran
bis(pinacol)diborane
A
4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane
Conditions | Yield |
---|---|
With (1,5-cyclooctadiene)(methoxy)iridium(I) dimer; 3,4,7,8-Tetramethyl-o-phenanthrolin; potassium tert-butylate at 110℃; for 20h; Reagent/catalyst; Glovebox; Inert atmosphere; Sealed tube; | A n/a B 88% |
perfluorooctyl-ethane
bis(pinacol)diborane
A
4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane
Conditions | Yield |
---|---|
(η5-pentamethylcyclopentadienyl)(η6-hexamethylbenzene)rhodium(I) In neat (no solvent) for 24 h at 150°C; various product yields for various conditions; | A n/a B 84% |
bis[dichloro(pentamethylcyclopentadienyl)ruthenium(III)] In octane 150°C, 24 h; |
hydrogen
bis(pinacol)diborane
4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane
Conditions | Yield |
---|---|
With (tBuPNN)CoCl2 In tetrahydrofuran; diethyl ether at 25℃; under 11251.1 Torr; for 9h; Solvent; Pressure; Autoclave; | 82% |
2,3-dimethyl-2,3-butane diol
4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane
Conditions | Yield |
---|---|
With dimethylsulfide borane complex In dichloromethane at 0 - 20℃; for 16h; Inert atmosphere; | 81% |
With dimethylsulfide borane complex In dichloromethane at 0 - 20℃; for 1.58333h; Inert atmosphere; | 81% |
Stage #1: 2,3-dimethyl-2,3-butane diol With borane-dimethyl sulfide complex In dichloromethane at 0℃; for 4h; Stage #2: In dichloromethane at 20℃; | 81.7% |
bis(pinacol)diborane
4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane
Conditions | Yield |
---|---|
With [(tBuPNN)FeCl2]; hydrogen; sodium t-butanolate In diethyl ether under 7500.75 Torr; for 2h; Catalytic behavior; Reagent/catalyst; Solvent; Autoclave; | 76% |
With palladium 10% on activated carbon; hydrogen In pentane at 20℃; under 750.075 Torr; for 20h; Pressure; Temperature; Time; Reagent/catalyst; Solvent; Inert atmosphere; Schlenk technique; Autoclave; | 47% |
methyl cyclohexane
bis(pinacol)diborane
A
4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane
Conditions | Yield |
---|---|
With carbon monoxide; pentamethylcyclopentadienyltricarbonylrhenium In pentane at 25℃; under 1520 Torr; for 60h; Borylation; Irradiation; | A 27 % Spectr. B 75% |
With carbon monoxide; pentamethylcyclopentadienyltricarbonylrhenium In neat (no solvent) Irradiation (UV/VIS); 25°C, 60 h; |
Tri(p-tolyl)phosphine
A
2,2'-(2,3-dimethyl-2,3-butanediyl-dioxy)bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane)
C
(pentamethylcyclopentadienyl)RhH(pinacolboryl)P(p-C6H4Me)3
D
bis(pinacolato)diborane
E
4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane
Conditions | Yield |
---|---|
heating dihydrido(pentamethylcyclopentadienyl)(dimethylphenylsilyl)(pinacolatoboryl)rhodium at 100°C with 1 equiv. of P(p-tol)3; | A n/a B 75% C 5% D n/a E n/a |
bis(pinacol)diborane
A
4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane
B
6-[2-(2,3-dimethyl-2,3-butanedioxy)hexyl]-4,4,5,5-methyl-1,3,2-dioxaborolane
Conditions | Yield |
---|---|
(η5-pentamethylcyclopentadienyl)(η6-hexamethylbenzene)rhodium(I) In neat (no solvent) for 24 h at 150°C; various product yields for various conditions; | A n/a B 70% |
Tri(p-tolyl)phosphine
A
2,2'-(2,3-dimethyl-2,3-butanediyl-dioxy)bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane)
C
(pentamethylcyclopentadienyl)RhH(pinacolboryl)P(p-C6H4Me)3
D
bis(pinacolato)diborane
E
4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane
Conditions | Yield |
---|---|
byproducts: HSiEt3; heating dihydrido(pentamethylcyclopentadienyl)(triethylsilyl)(pinacolatoboryl)rhodium at 100°C with 1 equiv. of P(p-tol)3; | A n/a B 68% C 13% D n/a E n/a |
1-ethyl-piperidine
bis(pinacol)diborane
A
4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane
Conditions | Yield |
---|---|
(η5-pentamethylcyclopentadienyl)(η6-hexamethylbenzene)rhodium(I) In neat (no solvent) for 24 h at 150°C; various product yields for various conditions; | A n/a B 67% |
bis[dichloro(pentamethylcyclopentadienyl)ruthenium(III)] In octane 150°C, 24 h; |
bis(pinacol)diborane
pentane
A
4,4,5,5-tetramethyl-2-pentyl-1,3,2-dioxaborolane
B
4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane
Conditions | Yield |
---|---|
With carbon monoxide; pentamethylcyclopentadienyltricarbonylrhenium at 25℃; under 1520 Torr; for 56h; Borylation; Irradiation; | A 65% B 32 % Spectr. |
With carbon monoxide; pentamethylcyclopentadienyltricarbonylrhenium In neat (no solvent) Irradiation (UV/VIS); 25°C, 56 h; chromy. (SiO2; pentane or pentane/Et2O); | A 65% B n/a |
1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone
bis(pinacol)diborane
A
1-methyl-3-((4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)methyl)tetrahydropyrimidin-2(1H)-one
B
4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane
Conditions | Yield |
---|---|
With methoxy(cyclooctadiene)rhodium(I) dimer In tetrahydrofuran at 70℃; for 6h; Inert atmosphere; Glovebox; | A 63% B n/a |
With methoxy(cyclooctadiene)rhodium(I) dimer In hexane at 70℃; for 3h; Inert atmosphere; regioselective reaction; |
dibutyl ether
bis(pinacol)diborane
A
4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane
Conditions | Yield |
---|---|
With carbon monoxide; pentamethylcyclopentadienyltricarbonylrhenium In pentane at 25℃; under 1520 Torr; for 45h; Borylation; Irradiation; | A 23 % Spectr. B 55% |
With carbon monoxide; pentamethylcyclopentadienyltricarbonylrhenium In neat (no solvent) Irradiation (UV/VIS); 25°C, 45 h; chromy. (SiO2; pentane or pentane/Et2O); | A n/a B 55% |
1-Fluoro-octane
bis(pinacol)diborane
A
4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane
Conditions | Yield |
---|---|
(η5-pentamethylcyclopentadienyl)(η6-hexamethylbenzene)rhodium(I) In neat (no solvent) for 12-24 h at 140-150°C; various product yields for various conditions; | A n/a B 46% |
2-pentylpyridine
bis(pinacol)diborane
A
2-(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pentyl)pyridine
B
4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane
Conditions | Yield |
---|---|
With (1,5-cyclooctadiene)(methoxy)iridium(I) dimer at 60℃; for 15h; Reagent/catalyst; Glovebox; Inert atmosphere; | A 42% B n/a |
tributyl-amine
bis(pinacol)diborane
A
4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane
Conditions | Yield |
---|---|
(η5-pentamethylcyclopentadienyl)(η6-hexamethylbenzene)rhodium(I) In neat (no solvent) for 24 h at 150°C; various product yields for various conditions; | A n/a B 33% |
chloro(pentamethylcyclopentadienyl)ruthenium(II) tetramer In octane 150°C, 24 h; |
methylbutane
bis(pinacol)diborane
A
4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane
Conditions | Yield |
---|---|
With carbon monoxide; pentamethylcyclopentadienyltricarbonylrhenium In pentane at 25℃; under 1520 Torr; for 55h; Borylation; Irradiation; | A 24 % Spectr. B n/a C n/a |
With carbon monoxide; pentamethylcyclopentadienyltricarbonylrhenium In neat (no solvent) Irradiation (UV/VIS); 25°C, 55 h; |
bis(pinacol)diborane
benzene
A
2-phenyl-4,4,5,5-tetramethyl-1,3,2-dioxoborole
B
4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane
Conditions | Yield |
---|---|
With carbon monoxide; [C5H4MeMn(CO)3] In pentane at 25℃; under 1520 Torr; for 36h; Borylation; Irradiation; | A 76 % Spectr. B 23 % Spectr. |
With carbon monoxide; methylcyclopentadienyl manganese(I) tricarbonyl In neat (no solvent) Irradiation (UV/VIS); 25°C, 36 h; |
2,3-dimethyl-2,3-butane diol
A
2,2'-(2,3-dimethyl-2,3-butanediyl-dioxy)bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane)
B
4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane
Conditions | Yield |
---|---|
With borane-ammonia complex In various solvent(s) at 20 - 25℃; for 0.5h; |
2,2-dimethylpentane
bis(pinacol)diborane
B
4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane
Conditions | Yield |
---|---|
bis[dichloro(pentamethylcyclopentadienyl)ruthenium(III)] In octane 150°C, 24 h; |
[Re(CO)2(BO2C2(CH3)4)2(C5(CH3)5)]
pentane
A
4,4,5,5-tetramethyl-2-pentyl-1,3,2-dioxaborolane
B
4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane
Conditions | Yield |
---|---|
In neat (no solvent) Irradiation (UV/VIS); |
4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane
Conditions | Yield |
---|---|
With P(CH2CH3)3 Kinetics; react. with excess of PEt3 at 100°C; half-life 2 h; NMR; |
4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane
Conditions | Yield |
---|---|
With P(CH2CH3)3 Kinetics; react. with excess of PEt3 at 100°C; half-life 4.5 h; NMR; |
4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane
benzene
2-phenyl-4,4,5,5-tetramethyl-1,3,2-dioxoborole
Conditions | Yield |
---|---|
[Ir(COD)(1,3-dicyclohexylimidazolidin-2-ylidene)2]CF3CO2 at 40℃; for 10h; | 100% |
(η4-1,5-cyclooctadiene)bis(1,3-dimethylimidazolin-2-ylidene)iridium(I) trifluoracetate In benzene (N2); using Schlenk techniques; dissolving of 2 mmol pinacolborane and 1.5 mol% of Ir(COD)(C3H2N2Me2)2(CF3CO2) in benzene; stirring and heating at 40°C for 12 h; monitoring by GC-MS; removal of solvent under vac. at room temp.; chromy. over silica gel, eluting with CH2Cl2; | 100% |
(η4-1,5-cyclooctadiene)(1,1'-dimethyl-3,3'-o-xylylene-diimidazolin-2,2'-diylidene)iridium(I) trifluoroacetate In benzene (N2); using Schlenk techniques; dissolving of 2 mmol pinacolborane and 1.5 mol% of Ir(COD)(1,1'-dimethyl-3,3'-o-xylylene-diimidazolin-2,2'-diylidene)2(CF3CO2) in benzene; stirring and heating at 40°C for 12 h; monitoring by GC-MS; removal of solvent under vac. at room temp.; chromy. over silica gel, eluting with CH2Cl2; | 100% |
bromobenzene
4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane
2-phenyl-4,4,5,5-tetramethyl-1,3,2-dioxoborole
Conditions | Yield |
---|---|
With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium acetate In 1,4-dioxane at 85℃; for 6h; Inert atmosphere; | 100% |
With bis(1,5-cyclooctadiene)diiridium(I) dichloride In methanol at 20℃; for 8h; | 92% |
Stage #1: bromobenzene; 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane With bis(trifluoromethane)sulfonimide lithium In tetrahydrofuran at 20℃; Electrochemical reaction; Stage #2: With sulfuric acid at 0℃; pH=5; Further stages.; | 78% |
phenylacetylene
4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane
4,4,5,5-tetramethyl-2-((E)-styryl)-[1,3,2]dioxaborolane
Conditions | Yield |
---|---|
With C39H22BF10OP In dichloromethane-d2 at 20℃; for 12h; Catalytic behavior; Reagent/catalyst; | 100% |
With tris(2,4,6-trifluorophenyl)borane triethylphosphine oxide In dichloromethane at 60℃; for 6h; Catalytic behavior; Reagent/catalyst; Solvent; Inert atmosphere; Sealed tube; | 99% |
Stage #1: 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane With C32H41CuN2O2S In toluene at 20℃; for 0.25h; Schlenk technique; Inert atmosphere; Stage #2: phenylacetylene In toluene at 20℃; for 2h; Catalytic behavior; Reagent/catalyst; Schlenk technique; Inert atmosphere; stereoselective reaction; | 98% |
2-methyl-but-2-ene
4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane
Conditions | Yield |
---|---|
With sodium triethylborohydride at 23℃; for 18h; Catalytic behavior; Inert atmosphere; | 100% |
With bis(1,5-cyclooctadiene)diiridium(I) dichloride In dichloromethane at 20℃; for 24h; | 36% |
With sodium triethylborohydride In tetrahydrofuran at 23℃; for 18h; Reagent/catalyst; Inert atmosphere; Glovebox; | 100 %Spectr. |
oct-1-ene
4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane
4,4,5,5-tetramethyl-2-octyl-[1,3,2]dioxaborolane
Conditions | Yield |
---|---|
With sodium triethylborohydride at 23℃; for 3h; Catalytic behavior; Reagent/catalyst; Inert atmosphere; | 100% |
Wilkinson's catalyst In dichloromethane 25°C, 10 min; | 99% |
With chlorocarbonylbis(triphenylphosphine)rhodium(I) In dichloromethane at 0 - 20℃; for 1.83333h; Inert atmosphere; | 99% |
4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane
isopropenylbenzene
2-(2-phenyl-2-methylethyl)-4,4,5,5-tetramethyl-[1,3,2]-dioxaborolane
Conditions | Yield |
---|---|
With sodium triethylborohydride at 23℃; Catalytic behavior; Inert atmosphere; | 100% |
With C39H48FeN2Si In benzene-d6 at 60℃; for 3h; Reagent/catalyst; Glovebox; Inert atmosphere; Schlenk technique; | 98% |
With bis(1,5-cyclooctadiene)rhodium(I) tetrafluoroborate; 1,4-di(diphenylphosphino)-butane In tetrahydrofuran at 20 - 40℃; for 16h; Inert atmosphere; | 96% |
4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane
Conditions | Yield |
---|---|
With triethylamine; bis-triphenylphosphine-palladium(II) chloride In 1,2-dichloro-ethane for 18h; Heating; | 100% |
bromobenzene
4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane
p-bromophenylboronic acid pinacol ester
Conditions | Yield |
---|---|
[Ir(COD)(1,3-dicyclohexylimidazolidin-2-ylidene)2]CF3CO2 at 40℃; for 10h; | 100% |
(η4-1,5-cyclooctadiene)bis(1,3-dimethylimidazolin-2-ylidene)iridium(I) trifluoracetate In further solvent(s) byproducts: H2; (N2); using Schlenk techniques; dissolving of 2 mmol pinacolborane and 1.5 mol% of Ir(COD)(C3H2N2Me2)2CF3CO2 in bromobenzene; stirring and heating at 40°C for 12 h; monitoring by GC-MS; removal of solvent under vac. at room temp.; chromy. over silica gel, eluting with CH2Cl2; | 100% |
(η4-1,5-cyclooctadiene)(1,1'-dimethyl-3,3'-o-xylylene-diimidazolin-2,2'-diylidene)iridium(I) trifluoroacetate In further solvent(s) (N2); using Schlenk techniques; dissolving of 2 mmol pinacolborane and 1.5 mol% of Ir(COD)(1,1'-dimethyl-3,3'-o-xylylene-diimidazolin-2,2'-diylidene)2CF3CO2 in bromobenzene; stirring and heating at 40°C for 12h; monitoring by GC-MS; removal of solvent under vac. at room temp.; chromy. over silica gel, eluting with CH2Cl2; | 100% |
iodobenzene
4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane
2-(4-iodophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
Conditions | Yield |
---|---|
[Ir(COD)(1,3-dicyclohexylimidazolidin-2-ylidene)2]CF3CO2 at 40℃; for 10h; | 100% |
(η4-1,5-cyclooctadiene)bis(1,3-dimethylimidazolin-2-ylidene)iridium(I) trifluoracetate In further solvent(s) byproducts: H2; (N2); using Schlenk techniques; dissolving of 2 mmol pinacolborane and 1.5 mol% of Ir(COD)(C3H2N2Me2)2CF3CO2 in IC6H5; stirring and heating at 40°C for 12 h; monitoring by GC-MS; removal of solvent under vac. at room temp.; chromy. over silica gel, eluting with CH2Cl2; | 100% |
(η4-1,5-cyclooctadiene)(1,1'-dimethyl-3,3'-o-xylylene-diimidazolin-2,2'-diylidene)iridium(I) trifluoroacetate In further solvent(s) (N2); using Schlenk techniques; dissolving of 2 mmol pinacolborane and 1.5 mol% of Ir(COD)(1,1'-dimethyl-3,3'-o-xylylene-diimidazolin-2,2'-diylidene)2CF3CO2 in iodobenzene; stirring and heating at 40°C for 12 h; monitoring by GC-MS; removal of solvent under vac. at room temp.; chromy. over silica gel, eluting with CH2Cl2; | 100% |
chlorobenzene
4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane
4-chlorophenylboronic acid pinacol ester
Conditions | Yield |
---|---|
[Ir(COD)(1,3-dicyclohexylimidazolidin-2-ylidene)2]CF3CO2 at 40℃; for 10h; | 100% |
(η4-1,5-cyclooctadiene)bis(1,3-dimethylimidazolin-2-ylidene)iridium(I) trifluoracetate In chlorobenzene byproducts: H2; (N2); using Schlenk techniques; dissolving of 2 mmol pinacolborane and 1.5 mol% of Ir(COD)(C3H2N2Me2)2(CF3CO2) in chlorobenzene; stirring and heating at 40°C for 12 h; monitoring by GC-MS; removal of solvent under vac. at room temp.; chromy. over silica gel, eluting with CH2Cl2; | 100% |
(η4-1,5-cyclooctadiene)(1,1'-dimethyl-3,3'-o-xylylene-diimidazolin-2,2'-diylidene)iridium(I) trifluoroacetate In chlorobenzene (N2); using Schlenk techniques; dissolving of 2 mmol pinacolborane and 1.5 mol% of Ir(COD)(1,1'-dimethyl-3,3'-o-xylylene-diimidazolin-2,2'-diylidene)2(CF3CO2) in chlorobenzene; stirring and heating at 40°C for12 h; monitoring by GC-MS; removal of solvent under vac. at room temp.; chromy. over silica gel, eluting with CH2Cl2; | 100% |
toluene
4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane
p-tolylboronic pinacol ester
Conditions | Yield |
---|---|
[Ir(COD)(1,3-dicyclohexylimidazolidin-2-ylidene)2]CF3CO2 at 40℃; for 10h; | 100% |
(η4-1,5-cyclooctadiene)bis(1,3-dimethylimidazolin-2-ylidene)iridium(I) trifluoracetate In toluene byproducts: H2; (N2); using Schlenk techniques; dissolving of 2 mmol pinacolborane and 1.5 mol% of Ir(COD)(C3H2N2Me2)2CF3CO2 in toluene; stirring and heating at40°C for 12 h; monitoring by GC-MS; removal of solvent under vac. at room temp.; chromy. over silica gel, eluting with CH2Cl2; | 100% |
(η4-1,5-cyclooctadiene)(1,1'-dimethyl-3,3'-o-xylylene-diimidazolin-2,2'-diylidene)iridium(I) trifluoroacetate In toluene (N2); using Schlenk techniques; dissolving of 2 mmol pinacolborane and 1.5 mol% of Ir(COD)(1,1'-dimethyl-3,3'-o-xylylene-diimidazolin-2,2'-diylidene)2(CF3CO2) in toluene; stirring and heating at 40°C for 12 h; monitoring by GC-MS; removal of solvent under vac. at room temp.; chromy. over silica gel, eluting with CH2Cl2; | 100% |
N-(t-butoxycarbonyl)-N-(2-(4-iodophenyl)ethyl)-N-(methylsulfonyl)amine
4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane
N-(t-butoxycarbonyl)-N-(methylsulfonyl)-N-(2-(4-(4,4,5,5-tetramethyl(1,3,2-dioxaborolan-2-yl))phenyl)ethyl)amine
Conditions | Yield |
---|---|
With triethylamine; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride In acetonitrile at 75℃; for 4h; Inert atmosphere; | 100% |
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; triethylamine In dichloromethane; acetonitrile at 70 - 74℃; for 8h; | 81% |
With triethylamine; 1,1'-bis(diphenylphosphino) ferrocene-dichloropalladium (II)-CH2Cl2 complex In acetonitrile at 70 - 74℃; for 8h; | 60.3% |
[4-(1-benzenesulfonyl-3-iodo-1H-pyrrolo[2,3-b]pyridin-5-yl)-phenyl]-dimethyl-amine
4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane
Conditions | Yield |
---|---|
With triethylamine; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 In 1,4-dioxane at 120℃; for 0.5h; Microwaves; | 100% |
[3-(4-bromophenyl)propoxy](tert-butyl)dimethylsilane
4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane
2-{4-[3-(tert-butyl-dimethyl-silanyloxy)-propyl]-phenyl}-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane
Conditions | Yield |
---|---|
With triethylamine; bis-triphenylphosphine-palladium(II) chloride In 1,4-dioxane at 100℃; for 16h; | 100% |
tert-butyl (((2S,3S,5R,6R)-2-ethynyl-5,6-dimethoxy-5,6-dimethyl-1,4-dioxan-2-yl)methoxy)dimethylsilane
4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane
tert-butyl (((2S,3S,5R,6R)-5,6-dimethoxy-5,6-dimethyl-3-((E)-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)vinyl)-1,4-dioxan-2-yl)methoxy)dimethylsilane
Conditions | Yield |
---|---|
at 100℃; for 24h; | 100% |
at 100 - 110℃; | 100% |
benzaldehyde
4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane
2-(benzyloxy)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
Conditions | Yield |
---|---|
With C27H44AlN3 In neat (no solvent) at 20℃; for 0.333333h; Inert atmosphere; Glovebox; | 100% |
With C28H26FeN2S4 In benzene-d6 at 20℃; for 0.5h; | 99% |
With sodium hydroxide; 1,3,5-trimethyl-benzene In chloroform at 20℃; for 0.25h; Reagent/catalyst; Solvent; Schlenk technique; Inert atmosphere; | 99% |
acetophenone
4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane
4,4,5,5-tetramethyl-2-(1-phenylethoxy)-1,3,2-dioxaborolane
Conditions | Yield |
---|---|
With Zr6(μ3-O)4(μ3-OMgMe)4(3'-nitro-[1,1':4',1'':4'',1'''-tetraphenyl]-4,4'''-dicarboxylate)6 In hexane at 23℃; for 24h; Catalytic behavior; Kinetics; Mechanism; Concentration; Solvent; Time; Inert atmosphere; Glovebox; Schlenk technique; | 100% |
With 6Zr(4+)*8O(2-)*6C26H15NO6(2-)*4Mg(2+)*4CH3(1-) In hexane at 23℃; for 24h; Catalytic behavior; Reagent/catalyst; Solvent; Temperature; Glovebox; | 100% |
With Nd(Cp)3 In tetrahydrofuran at 20℃; for 1h; Reagent/catalyst; Inert atmosphere; | 99% |
[5,10-bis(3,5-di-tert-butylphenyl)-15,20-dibromoporphyrinato]zinc(II)
4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane
5,10-bis[3,5-di(tert-butyl)phenyl]-15,20-bis(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)porphyrinato-N(21),N(22),N(23),N(24)zinc(II)
Conditions | Yield |
---|---|
With bis-triphenylphosphine-palladium(II) chloride; water; triethylamine In 1,2-dichloro-ethane for 1.5h; Suzuki-Miyaura cross-coupling; Inert atmosphere; Reflux; | 100% |
[5,15-dibromo-10,20-bis-(3,5-di-tert-butyphenyl)porphyrinato]zinc(II)
4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane
5,15-bis[3,5-di(tert-butyl)phenyl]-10,20-bis(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)porphyrinato-N(21),N(22),N(23),N(24)zinc(II)
Conditions | Yield |
---|---|
With bis-triphenylphosphine-palladium(II) chloride; water; triethylamine In 1,2-dichloro-ethane for 1.5h; Suzuki-Miyaura cross-coupling; Inert atmosphere; Reflux; | 100% |
With bis-triphenylphosphine-palladium(II) chloride; triethylamine In tetrahydrofuran; toluene at 60℃; Inert atmosphere; | 74% |
With pyridine; triethylamine; bis-triphenylphosphine-palladium(II) chloride In toluene for 1h; Inert atmosphere; Reflux; |
but-1-yne
4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane
2-[(1E)-but-1-en-1-yl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
Conditions | Yield |
---|---|
With zirconocene dichloride; lithium triethylborohydride; triethylamine In tetrahydrofuran at -78 - 20℃; Inert atmosphere; | 100% |
Stage #1: but-1-yne; 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane at -78℃; for 0.5h; Inert atmosphere; Stage #2: With bis(pentamethylcyclopentadienyl)zirconium(IV) dichloride; lithium triethylborohydride; triethylamine In tetrahydrofuran at -78 - 20℃; for 20h; | 65% |
With bis(cyclohexanyl)borane In neat (no solvent) at -78 - 0℃; for 6h; Glovebox; Inert atmosphere; enantioselective reaction; |
tert-butyl(5-hexenyloxy)dimethylsilane
4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane
tert-butyldimethyl ((6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)hexyl)oxy)silane
Conditions | Yield |
---|---|
With bis(1,5-cyclooctadiene)diiridium(I) dichloride; 1,2-bis-(diphenylphosphino)ethane In dichloromethane at 0 - 20℃; Inert atmosphere; | 100% |
With bis(1,5-cyclooctadiene)diiridium(I) dichloride; 1,2-bis-(diphenylphosphino)ethane In dichloromethane at 20℃; for 6h; | 96% |
2-methyl-3-bromo-1-propene
4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane
4,4,5,5-tetramethyl-2-(2-methylallyl)-1,3,2-dioxaborolane
Conditions | Yield |
---|---|
With magnesium In tetrahydrofuran at 25℃; for 2.08333h; Inert atmosphere; | 100% |
With magnesium In tetrahydrofuran at 25℃; for 2.5h; | 69% |
With magnesium In tetrahydrofuran at 20℃; for 2h; Inert atmosphere; Schlenk technique; | 65% |
N-[3-(4-bromo-1-isopropyl-3H-pyrazol-3-yl)-2-fluorophenyl]-2,5-difluoro-N-methoxymethylbenzenesulfonamide
4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane
2,5-difluoro-N-{2-fluoro-3-[1-isopropyl-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1H-pyrazol-3-yl]phenyl}-N-methoxymethylbenzenesulfonamide
Conditions | Yield |
---|---|
With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; triethylamine; bis(acetonitrile)palladium(II) dichloride In toluene at 90℃; for 1h; Microwave irradiation; Inert atmosphere; | 100% |
4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane
Conditions | Yield |
---|---|
In benzene-d6 at 0℃; for 0.0166667h; Inert atmosphere; | 100% |
benzophenone
4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane
2-[(benzhydryl)oxy]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
Conditions | Yield |
---|---|
With C32H45F3N2O4SZn In tetrahydrofuran at 25℃; for 0.0833333h; Catalytic behavior; Reagent/catalyst; Inert atmosphere; | 100% |
With C37H76N6Si6Th In benzene-d6 at 25℃; for 0.166667h; Catalytic behavior; Glovebox; Sealed tube; Schlenk technique; chemoselective reaction; | 100% |
With C26H60AlLiN4 In benzene-d6 at 20℃; for 3h; Reagent/catalyst; Inert atmosphere; | 99% |
6-(N-(2-(benzyloxymethyl)allyl)-2-methylpropylsulfonamido)-5-cyclopropyl-2-(4-fluorophenyl)-N-methylbenzofuran-3-carboxamide
4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane
6-(N-(3-(benzyloxy)-2-((4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)methyl)propyl)-2-methylpropylsulfonamido)-5-cyclopropyl-2-(4-fluorophenyl)-N-methylbenzofuran-3-carboxamide
Conditions | Yield |
---|---|
carbonylbis(triphenylphosphine)rhodium(1)chloride In tetrahydrofuran for 3h; Inert atmosphere; | 100% |
isovaleraldehyde
4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane
2-(isopentyloxy)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
Conditions | Yield |
---|---|
With [HC(CMeN(2,6-(isopropyl)2C6H3)2)]Al(hydride)(triflate) In benzene-d6 at 20℃; for 1h; Inert atmosphere; Sealed tube; | 100% |
With catalyst:C4H9Mg(2,6-iPr2C6H3NCCH3)CH In benzene-d6 pinacolborane reacted with aldehyde in C6D6 at 25°C catalized by nBuMg(2,6-iPrC6H3NCCH3)2CH 0.1-0.5 mol% for <0.5 h; | |
With 2-H-1,3-di-tert-butyl-2,3-dihydro-1H-1,3,2-diazaphosphole In [D3]acetonitrile at 20℃; for 9h; Catalytic behavior; Inert atmosphere; Sealed tube; | 88 %Spectr. |
tert-butyl (1-(4-bromo-3-methylisoxazol-5-yl)cyclopropyl)carbamate
4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane
tert-butyl (1-(3-methyl-4-(4,4,5,5-tetramethyl1,3,2-dioxaborolan-2-yl)isoxazol-5-yl)cyclopropyl)carbamate
Conditions | Yield |
---|---|
With triethylamine; dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; dichloro bis(acetonitrile) palladium(II) In 1,4-dioxane at 100℃; for 1h; Inert atmosphere; | 100% |
4-Methylbenzophenone
4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane
2-(1-(4-methylphenyl)-1-phenylmethoxy)pinacolborane
Conditions | Yield |
---|---|
With C37H76N6Si6Th In benzene-d6 at 25℃; for 0.166667h; Catalytic behavior; Glovebox; Sealed tube; Schlenk technique; chemoselective reaction; | 100% |
With titanocene bis(catecholborane) In toluene; pentane at 20℃; for 2h; Inert atmosphere; Schlenk technique; Glovebox; | 69% |
With tris[N,N-bis(trimethylsilyl)amide]lanthanum(III) In benzene-d6 at 25℃; for 0.25h; | > 99 %Spectr. |
With C48H57HfN3 In benzene-d6 at 25℃; for 0.25h; Reagent/catalyst; Glovebox; | 99 %Spectr. |
7-bromo-3-cyclopropylbenzo[d]isoxazole
4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane
3-cyclopropyl-7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzo[d]isoxazole
Conditions | Yield |
---|---|
With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; dichloro bis(acetonitrile) palladium(II); triethylamine In 1,4-dioxane at 110℃; for 19h; Inert atmosphere; Sealed tube; | 100% |
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