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Conditions | Yield |
---|---|
at 110℃; for 6h; | 100% |
at 110℃; for 6h; Inert atmosphere; Neat (no solvent); | 100% |
Stage #1: phenylboronic acid With barium(II) hydroxide In water at 80℃; for 0.0833333h; Stage #2: With Au38(SCH2CH2Ph)24 In toluene at 80℃; for 12h; Reagent/catalyst; | 100% |
N-(4-chlorobenzylidene)-4-methylbenzenesulfonamide
phenylboronic acid
triphenylboroxine
Conditions | Yield |
---|---|
In toluene for 12h; Dean-Stark; Reflux; | 99% |
Conditions | Yield |
---|---|
In neat (no solvent) refluxing equimolar amounts for 48h;; dissolving in CCl4,; | 91% |
In neat (no solvent) |
Conditions | Yield |
---|---|
With potassium carbonate In ethanol at 78℃; for 1h; Catalytic behavior; Reagent/catalyst; Suzuki-Miyaura Coupling; | A n/a B 87% |
With potassium carbonate In ethanol at 78℃; for 1h; Suzuki-Miyaura Coupling; | A 49% B 6% |
Conditions | Yield |
---|---|
With water; pyridin-2-ylmethyl methanesulphonate In tetrahydrofuran; toluene at 90℃; for 0.666667h; Temperature; Inert atmosphere; | 80.26% |
diphenyl(diethylamino)borane
N,N'-Bis-(diphenylboryl)-hydrazin
(n-C4H9)2BNHNC6H5B(n-C4H9)2
triphenylboroxine
Conditions | Yield |
---|---|
byproducts: (C6H5)2CNNC(C6H5)2; 80°C, reflux, 1.5 h; | 75% |
byproducts: (C6H5)2CNNC(C6H5)2; 80°C, reflux, 1.5 h; | 75% |
2-phenyl-4H-benzo-1,3,2-dioxaborine
A
triphenylboroxine
B
9',9'A-dihydro-4'aH-spiro[chroman-2,1'-xanthen]-2'-one
C
C28H24O4
Conditions | Yield |
---|---|
at 900℃; under 0.005 Torr; | A 70% B 12% C 31% |
piperazine
phenylboronic acid
A
triphenylboroxine
B
4-phenyl-1-piperazine
C
biphenyl
Conditions | Yield |
---|---|
With [Cu4I4(1,4-diazabicyclo[2.2.2]octane)2]n In methanol at 27℃; for 5h; | A 9 %Chromat. B 68% C 20 %Chromat. |
2,4-diphenylbenzo[j]-9-methyl-8-aza-1,3,5,2,4-trioxadiboracycloundec-8-ene
A
triphenylboroxine
B
(rac)-2-(phenyl)benzo[j]-7-methyl-6-aza-1,3-dioxa-2-boracyclononen-6-ene
Conditions | Yield |
---|---|
In toluene for 24h; Reflux; diastereoselective reaction; | A n/a B 60% |
2,4-diphenylbenzo[j]-9-methyl-8-aza-1,3,5,2,4-trioxadiboracycloundec-8-ene
phenylboronic acid
A
triphenylboroxine
B
(rac)-2-(phenyl)benzo[j]-7-methyl-6-aza-1,3-dioxa-2-boracyclononen-6-ene
Conditions | Yield |
---|---|
In toluene soln. of C6H4C(CH3)N(C2H4OB(C6H5)O)B(C6H5) refluxed for 24 h; solvent and water eliminated, residue washed with CH3Cl, recrystd. from chloroform; elem. anal.; | A n/a B 60% |
Conditions | Yield |
---|---|
With bis(acetylacetonate)nickel(II); potassium phosphate; oxygen In tetrahydrofuran for 12h; Inert atmosphere; Reflux; | A 60% B 20% C 10% |
Conditions | Yield |
---|---|
With bis(acetylacetonate)nickel(II); potassium phosphate; oxygen-18 In tetrahydrofuran for 12h; Reflux; | A 33% B 12% C 42% |
2,5-diphenyl-1,3,2,5-dioxaborataphosphorinane
triphenylboroxine
Conditions | Yield |
---|---|
With methyl iodide In diethyl ether byproducts: bis(hydroxymethyl)methyl(phenyl)phosphonium iodide; heated for 1 h at reflux with protection from atmospheric moisture; solvent removed; residue crystd. (acetone); IR; NMR; elem. anal.; | 40% |
(trifluoromethyl)trimethylsilane
phenylboronic acid
A
triphenylboroxine
B
phenyl trifluoromethylsulfide
C
diphenyldisulfane
Conditions | Yield |
---|---|
With potassium fluoride; potassium phosphate; copper(l) iodide; 1,10-Phenanthroline; sulfur; silver carbonate In N,N-dimethyl-formamide at 20℃; Molecular sieve; | A n/a B 33% C n/a |
Conditions | Yield |
---|---|
at 230℃; |
Conditions | Yield |
---|---|
at 175℃; |
Conditions | Yield |
---|---|
With boron trioxide |
Conditions | Yield |
---|---|
Einwirkung von Luftfeuchtigkeit; | |
Multi-step reaction with 2 steps 1: H2S2 / CS2 2: (hydrolysis) View Scheme | |
Multi-step reaction with 2 steps 1: diethyl ether 2: SO2 View Scheme |
Conditions | Yield |
---|---|
Beim Aufbewahren; | |
room. temp., 1 day; |
Conditions | Yield |
---|---|
With boron trichloride; benzene at 180 - 200℃; ueber mehrere Stufen; |
3,5-diphenyl-1,2,4,3,5-trithiaborolane
triphenylboroxine
Conditions | Yield |
---|---|
(hydrolysis); |
triphenylboroxine
Conditions | Yield |
---|---|
With sulfuric acid In 1,4-dioxane Heating; |
boric acid tributyl ester
1,2-dibromobenzene
A
triphenylboroxine
B
1-butylene
C
(Z)-2-Butene
D
trans-2-Butene
Conditions | Yield |
---|---|
bei der Destillation; | |
In neat (no solvent) on standing at room temp., reversible react.;; | |
In neat (no solvent) | |
In tetrahydrofuran-d8 at 25℃; Equilibrium constant; |
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: benzene; boron trichloride / 180 - 200 °C / ueber mehrere Stufen 2: Einwirkung von Luftfeuchtigkeit View Scheme |
3,5-dimethylphenyl boronic acid
phenylboronic acid
A
triphenylboroxine
D
tris(3.5-dimethyl phenyl)boroxine
Conditions | Yield |
---|---|
With water at 25℃; |
Conditions | Yield |
---|---|
dehydration at 115°C;; |
Conditions | Yield |
---|---|
In neat (no solvent) on heating in vac.;; | |
In neat (no solvent) |
triphenylboroxine
N-(3,5-dimethylphenyl)-benzamide
Conditions | Yield |
---|---|
With potassium fluoride; chloro(1,5-cyclooctadiene)rhodium(I) dimer In 1,4-dioxane at 100℃; for 24h; Inert atmosphere; Sealed tube; | 100% |
With potassium fluoride; chloro(1,5-cyclooctadiene)rhodium(I) dimer In 1,4-dioxane at 100℃; for 24h; | 100% |
triphenylboroxine
N-(4-chlorobenzylidene)-4-methylbenzenesulfonamide
A
(R)-N-((4-chlorophenyl)(phenyl)methyl)-4-methylbenzenesulfonamide
B
(S)-N-((4-chlorophenyl)(phenyl)methyl)-4-methylbenzenesulfonamide
Conditions | Yield |
---|---|
With di-μ-chloro-bis[(η5-(4`R,5`R)-(Sp)-2-(2`-4`,5`-dihydro-4`,5`-diphenyl-1`-tosyl-1`H-imidazolyl)cyclopentadienyl,1-C,3`-N)(η5-cyclopentadienyl)-iron(II)]dipalladium(II); silver(I) acetate In chlorobenzene at 65℃; for 20h; Inert atmosphere; | A 100% B 11% |
triphenylboroxine
(E)-N-(furan-2-ylmethylene)-4-methylbenzenesulfonamide
(S)-N-((furan-2-yl(phenyl)methyl)-4-methylbenzenesulfonamide)
Conditions | Yield |
---|---|
With potassium hydroxide; bis(ethylene)rhodium(I) chloride dimer; (1R,4R)-2,5-diphenylbicyclo[2.2.2]octa-2,5-diene In 1,4-dioxane at 60℃; for 6h; | 99% |
triphenylboroxine
(S)-3-methyl-2-[(napthalen-1ylmethyl)-amino]-1,1-diphenyl-butan-1-ol
Conditions | Yield |
---|---|
In toluene microwave irradiation; | 99% |
With 4 A molecular sieve In toluene for 15h; microwave heating; | |
In toluene at 200℃; Molecular sieve; Inert atmosphere; Microwave irradiation; |
triphenylboroxine
(2S)-3-methyl-2-[(octyl)amino]-1,1-diphenyl-butan-1-ol
Conditions | Yield |
---|---|
In toluene microwave irradiation; | 99% |
Conditions | Yield |
---|---|
With sodium t-butanolate; bis(1,5-cyclooctadiene)nickel (0) In 1,2-dimethoxyethane; water at 100℃; for 48h; | 99% |
With bis(1,5-cyclooctadiene)nickel(0); (+/-)-Et-Duphos; sodium t-butanolate In 1,2-dimethoxyethane; water at 100℃; for 48h; | 99% |
Stage #1: triphenylboroxine With bis(1,5-cyclooctadiene)nickel(0); potassium phosphate; 4-chlorobenzophenone In tetrahydrofuran at 20℃; Stage #2: ortho-anisaldehyde In tetrahydrofuran at 20℃; | 85% |
triphenylboroxine
3-methoxy-benzaldehyde
m-methoxybenzhydrol
Conditions | Yield |
---|---|
With sodium t-butanolate; bis(1,5-cyclooctadiene)nickel (0) In 1,2-dimethoxyethane; water at 100℃; for 48h; | 99% |
With bis(1,5-cyclooctadiene)nickel(0); (+/-)-Et-Duphos; sodium t-butanolate In 1,2-dimethoxyethane; water at 100℃; for 48h; | 99% |
Conditions | Yield |
---|---|
Stage #1: triphenylboroxine; (2E,4E)-N,N-diphenyl-2,4-hexadienamide With [IrCl((S,S)-Me-tfb*)]2; potassium carbonate In methanol at 30℃; for 20h; Stage #2: With Crabtree's catalyst; hydrogen In dichloromethane at 20℃; under 760.051 Torr; for 12h; optical yield given as %ee; enantioselective reaction; | 99% |
triphenylboroxine
3-methylcyclohexen-2-one
(R)-3-methyl-3-phenylcyclohexan-1-one
Conditions | Yield |
---|---|
Stage #1: triphenylboroxine; 3-methylcyclohexen-2-one With 2C24H14F4*2HO(1-)*2Rh(1+) In 1,4-dioxane at 60℃; for 24h; Inert atmosphere; Stage #2: With water In 1,4-dioxane Inert atmosphere; optical yield given as %ee; enantioselective reaction; | 99% |
triphenylboroxine
3-hydroxy-3-(4-methoxyphenyl)-2,3-dihydro-1H-isoindol-1-one
Conditions | Yield |
---|---|
With C64H46F8Fe4O2Rh2 In 1,4-dioxane at 80℃; for 24h; Schlenk technique; Inert atmosphere; enantioselective reaction; | 99% |
Conditions | Yield |
---|---|
Stage #1: triphenylboroxine With ammonium hexafluorophosphate; palladium(II) trifluoroacetate; 2-[(S)-4,5-dihydro-4-tert-butyl-1,3-oxazol-2-yl]pyridine In 1,2-dichloro-ethane at 20℃; for 0.0333333h; Glovebox; Stage #2: 3-methylcyclohexen-2-one With water-d2 In 1,2-dichloro-ethane for 12h; Glovebox; enantioselective reaction; | 99% |
triphenylboroxine
2-furaldehyde tosylimine
(S)-N-((furan-2-yl(phenyl)methyl)-4-methylbenzenesulfonamide)
Conditions | Yield |
---|---|
With chlorobis(ethylene)rhodium(I) dimer; (S)-(-)-[η5-1-bis(3,5-di(trifluormethylphenyl)phosphino-2-(3-diphenylphosphino-2-methylpropenyl)cyclopentadienyl-P)]manganese(I) dicarbonyl; potassium hydroxide In 1,4-dioxane; water at 40℃; for 7h; Reagent/catalyst; Inert atmosphere; enantioselective reaction; | 99% |
With chlorobis(ethylene)rhodium(I) dimer; potassium hydroxide; (1R,4R)-2,5-diphenylbicyclo[2.2.2]octa-2,5-diene In 1,4-dioxane; water at 60℃; for 6h; | 97% |
With chlorobis(ethylene)rhodium(I) dimer; potassium hydroxide; (1R,4R)-2,5-diphenylbicyclo[2.2.2]octa-2,5-diene In 1,4-dioxane; water at 20 - 60℃; for 6.25h; Inert atmosphere; | 97% |
triphenylboroxine
3-butyl-1,2-benzisothiazole-1,1-dioxide
Conditions | Yield |
---|---|
Stage #1: triphenylboroxine; 3-butyl-1,2-benzisothiazole-1,1-dioxide With chlorobis(cyclooctene)rhodium(I) dimer; C18H23NOS In 1,2-dichloro-ethane at 20℃; for 0.5h; Inert atmosphere; Stage #2: With potassium hydroxide In water; 1,2-dichloro-ethane at 60℃; for 12h; Inert atmosphere; enantioselective reaction; | 99% |
triphenylboroxine
3-benzyl-1,2-benzisothiazole-1,1-dioxide
Conditions | Yield |
---|---|
Stage #1: triphenylboroxine; 3-benzyl-1,2-benzisothiazole-1,1-dioxide With chlorobis(cyclooctene)rhodium(I) dimer; C18H23NOS In 1,2-dichloro-ethane at 20℃; for 0.5h; Inert atmosphere; Stage #2: With potassium hydroxide In water; 1,2-dichloro-ethane at 60℃; for 12h; Inert atmosphere; enantioselective reaction; | 99% |
triphenylboroxine
Conditions | Yield |
---|---|
Stage #1: triphenylboroxine; 3-cyclohexyl-1,2-benziothiazole-1,1-dioxide With chlorobis(cyclooctene)rhodium(I) dimer; C18H23NOS In 1,2-dichloro-ethane at 20℃; for 0.5h; Inert atmosphere; Stage #2: With potassium hydroxide In water; 1,2-dichloro-ethane at 60℃; for 12h; Inert atmosphere; enantioselective reaction; | 99% |
triphenylboroxine
3-methylbenzo[d]isothiazole-1,1-dioxide
Conditions | Yield |
---|---|
Stage #1: triphenylboroxine; 3-methylbenzo[d]isothiazole-1,1-dioxide With chlorobis(cyclooctene)rhodium(I) dimer; C18H23NOS In 1,2-dichloro-ethane at 20℃; for 0.5h; Inert atmosphere; Stage #2: With potassium hydroxide In water; 1,2-dichloro-ethane at 60℃; for 12h; Inert atmosphere; enantioselective reaction; | 99% |
triphenylboroxine
N-(4-chlorobenzylidene)-4-methylbenzenesulfonamide
(R)-N-((4-chlorophenyl)(phenyl)methyl)-4-methylbenzenesulfonamide
Conditions | Yield |
---|---|
With di-μ-chlorobis[η5-(4'R,5'R)-(Sp)-2-(2'-4',5'-dihydro-4',5'-diphenyl-1'-tosyl-1'H-imidazolyl)cyclopentadienyl, (1-C,3'-N)(η5-cyclopentadienyl)-iron(II)]dipalladium(II); silver(I) acetate In chlorobenzene; acetonitrile at 65℃; for 20h; Reagent/catalyst; Temperature; Inert atmosphere; enantioselective reaction; | 99% |
With di-μ-chloro-bis[(η5-(4`R,5`R)-(Sp)-2-(2`-4`,5`-dihydro-4`,5`-diphenyl-1`-tosyl-1`H-imidazolyl)cyclopentadienyl,1-C,3`-N)(η5-cyclopentadienyl)-iron(II)]dipalladium(II); silver(I) acetate In chlorobenzene at 65℃; for 20h; Reagent/catalyst; Solvent; Temperature; Inert atmosphere; Schlenk technique; enantioselective reaction; | 99% |
With chlorobis(ethylene)rhodium(I) dimer; (R)-4-isopropyl-3-((1R,4S)-3-phenylbicyclo[2.2.1]hepta-2,5-diene-2-carbonyl)oxazolidin-2-one; potassium hydroxide; n-octyl β-D-glucopyranoside In 1,4-dioxane; water at 29.84℃; for 1h; Reagent/catalyst; Solvent; Inert atmosphere; | 99% |
triphenylboroxine
N-(2-methylphenyl)methylidene-4-methylbenzenesulfonamide
(S)-N-[(2-methylphenyl)phenylmethyl]-4-methylbenzenesulfonamide
Conditions | Yield |
---|---|
With chlorobis(ethylene)rhodium(I) dimer; potassium hydroxide In tetrahydrofuran at 60℃; for 24h; enantioselective reaction; | 99% |
With [{(M,SS,SS)-p-Tol-binaso}Rh(OH)]2 In water; toluene at 25℃; for 14h; Glovebox; Sealed tube; Inert atmosphere; enantioselective reaction; | 95% |
triphenylboroxine
N-[1-(3-Methoxy-phenyl)-meth-(E)-ylidene]-4-methyl-benzenesulfonamide
Conditions | Yield |
---|---|
With chlorobis(ethylene)rhodium(I) dimer; potassium hydroxide In tetrahydrofuran at 60℃; for 24h; enantioselective reaction; | 99% |
With [{(M,SS,SS)-p-Tol-binaso}Rh(OH)]2 In water; toluene at 25℃; for 14h; Glovebox; Sealed tube; Inert atmosphere; enantioselective reaction; | 88% |
triphenylboroxine
N-(4-methoxybenzylidene)-p-toluenesulfonamide
(S)-N-((4-methoxyphenyl)(phenyl)methyl)-4-methylbenzenesulfonamide
Conditions | Yield |
---|---|
With chlorobis(ethylene)rhodium(I) dimer; (S)-(-)-[η5-1-bis(3,5-di(trifluormethylphenyl)phosphino-2-(3-diphenylphosphino-2-methylpropenyl)cyclopentadienyl-P)]manganese(I) dicarbonyl; potassium hydroxide In 1,4-dioxane; water at 40℃; for 7h; Reagent/catalyst; Inert atmosphere; enantioselective reaction; | 99% |
With chlorobis(ethylene)rhodium(I) dimer; potassium hydroxide In tetrahydrofuran at 60℃; for 24h; enantioselective reaction; | 29% |
triphenylboroxine
N-(2-methoxybenzylidene)-p-toluenesulfonamide
(S)-N-((2-methoxyphenyl)(phenyl)methyl)-4-methylbenzenesulfonamide
Conditions | Yield |
---|---|
With chlorobis(ethylene)rhodium(I) dimer; (S)-(-)-[η5-1-bis(3,5-di(trifluormethylphenyl)phosphino-2-(3-diphenylphosphino-2-methylpropenyl)cyclopentadienyl-P)]manganese(I) dicarbonyl; potassium hydroxide In 1,4-dioxane; water at 40℃; for 7h; Reagent/catalyst; Inert atmosphere; enantioselective reaction; | 99% |
triphenylboroxine
4-methyl-N-(thiophen-2-ylmethylene)benzenesulfonamide
Conditions | Yield |
---|---|
With chlorobis(ethylene)rhodium(I) dimer; (S)-(-)-[η5-1-bis(3,5-di(trifluormethylphenyl)phosphino-2-(3-diphenylphosphino-2-methylpropenyl)cyclopentadienyl-P)]manganese(I) dicarbonyl; potassium hydroxide In 1,4-dioxane; water at 40℃; for 7h; Reagent/catalyst; Inert atmosphere; enantioselective reaction; | 99% |
Conditions | Yield |
---|---|
Stage #1: triphenylboroxine; C27H34N2O3SSi With [RhCl(cis-cyclooctene)2]2; (R)-N-(4,4-dimethyl-2-methylenepentyl)-2-methylpropane-2-sulfinamide In toluene at 20℃; for 0.5h; Schlenk technique; Inert atmosphere; Stage #2: With potassium hydroxide In water; toluene at 60℃; for 6h; | 99% |
Conditions | Yield |
---|---|
With [Rh(OH)((S)-binap)]2 at 35℃; for 3h; | 98% |
With potassium hydroxide; [RhCl((S,S)-2,5-dibenzylbicyclo[2.2.2]octa-2,5-diene)]2 In 1,4-dioxane; water at 30℃; for 1h; | 96% |
triphenylboroxine
N-(2-methoxyphenyl)methylidene-4-methylbenzenesulfonamide
(S)-N-((2-methoxyphenyl)(phenyl)methyl)-4-methylbenzenesulfonamide
Conditions | Yield |
---|---|
With potassium hydroxide; bis(ethylene)rhodium(I) chloride dimer; (1R,4R)-2,5-diphenylbicyclo[2.2.2]octa-2,5-diene In 1,4-dioxane at 60℃; for 6h; | 98% |
triphenylboroxine
N-[(S)-(4-methoxyphenyl)(phenyl)methyl]-4-nitrobenzenesulfonamide
Conditions | Yield |
---|---|
With potassium hydroxide; [RhCl((1R,5R)-2,6-diphenylbicyclo[3.3.1]nona-2,6-diene)]2 In 1,4-dioxane at 60℃; for 6h; | 98% |
triphenylboroxine
N-(4-bromophenyl)methylidene-4-nitrobenzenesulfonamide
(S)-N-[(4-bromophenyl)phenylmethyl]-4-nitrobenzenesulfonamide
Conditions | Yield |
---|---|
With potassium hydroxide; [RhCl((1R,5R)-2,6-diphenylbicyclo[3.3.1]nona-2,6-diene)]2 In 1,4-dioxane at 60℃; for 6h; | 98% |
Conditions | Yield |
---|---|
Stage #1: triphenylboroxine With diethylzinc In toluene at 60℃; for 4h; Stage #2: 4-fluorobenzaldehyde With (S)-dendritic pyrrolidinylmethanol C116H105NO15 In toluene at -15℃; for 6h; | 98% |
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