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75927-49-0

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75927-49-0 Usage

Uses

Different sources of media describe the Uses of 75927-49-0 differently. You can refer to the following data:
1. suzuki reaction
2. Reagent used forSuzuki-Miyaura coupling reactionsMizoroki-Heck reactions (cascade reaction)Intramolecular Nozaki-Hiyama-Kishi reactionsStereoselective Cu-catalyzed γ-selective and stereospecific couplingControl of stereoselectivity and mechanistic portrait on intramolecular (4+1)-cycloaddition of dialkoxycarbenesRegio- and stereoselective synthesis of trisubstituted alkenes via gold(I)-catalyzed hydrophosphoryloxylation of haloalkynes followed by Pd-catalyzed consecutive cross-coupling reactionsAsymmetric Birch reductive alkylationReagent used in Preparation of Molecular tubes for lipid sensingEnzymatic inhibitors, antibiotics, receptor analogs, and other biologically significant compounds (including total syntheses)

Check Digit Verification of cas no

The CAS Registry Mumber 75927-49-0 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 7,5,9,2 and 7 respectively; the second part has 2 digits, 4 and 9 respectively.
Calculate Digit Verification of CAS Registry Number 75927-49:
(7*7)+(6*5)+(5*9)+(4*2)+(3*7)+(2*4)+(1*9)=170
170 % 10 = 0
So 75927-49-0 is a valid CAS Registry Number.
InChI:InChI=1/C8H16BO3/c1-6-9(11)12-8(4,5)7(2,3)10/h6,10H,1H2,2-5H3/q-1

75927-49-0 Well-known Company Product Price

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  • TCI America

  • (T2297)  4,4,5,5-Tetramethyl-2-vinyl-1,3,2-dioxaborolane (stabilized with Phenothiazine)  >95.0%(GC)

  • 75927-49-0

  • 1g

  • 550.00CNY

  • Detail
  • TCI America

  • (T2297)  4,4,5,5-Tetramethyl-2-vinyl-1,3,2-dioxaborolane (stabilized with Phenothiazine)  >95.0%(GC)

  • 75927-49-0

  • 5g

  • 1,690.00CNY

  • Detail
  • TCI America

  • (T2297)  4,4,5,5-Tetramethyl-2-vinyl-1,3,2-dioxaborolane (stabilized with Phenothiazine)  >95.0%(GC)

  • 75927-49-0

  • 25g

  • 4,900.00CNY

  • Detail

75927-49-0SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 12, 2017

Revision Date: Aug 12, 2017

1.Identification

1.1 GHS Product identifier

Product name Vinylboronic Acid Pinacol Ester

1.2 Other means of identification

Product number -
Other names 2-ethenyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:75927-49-0 SDS

75927-49-0Synthetic route

ethene
74-85-1

ethene

4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane
25015-63-8

4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane

A

ethylboronic acid pinacol ester
82954-89-0

ethylboronic acid pinacol ester

B

pinacol vinylboronate
75927-49-0

pinacol vinylboronate

Conditions
ConditionsYield
RuH2(H2)2(tricyclohexylphosphine)2 In tolueneA n/a
B 23%
[Ru(H)((μ-H)2B(OC(CH3)2)2)(σ-HB(OC(CH3)2)2)(P(C6H11)3)2 In toluene
2,3-dimethyl-2,3-butane diol
76-09-5

2,3-dimethyl-2,3-butane diol

vinylboronic acid
4363-34-2

vinylboronic acid

pinacol vinylboronate
75927-49-0

pinacol vinylboronate

Conditions
ConditionsYield
In diethyl ether at 20℃; for 12h;
2,3-dimethyl-2,3-butane diol
76-09-5

2,3-dimethyl-2,3-butane diol

vinylbis(diisopropylamino)borane
151293-63-9

vinylbis(diisopropylamino)borane

pinacol vinylboronate
75927-49-0

pinacol vinylboronate

Conditions
ConditionsYield
With 2,6-di-tert-butyl-4-methyl-phenol at 85 - 90℃; Reagent/catalyst; Inert atmosphere;252 g
bis(pinacol)diborane
73183-34-3

bis(pinacol)diborane

A

2,2',2''-(ethane-1,1,2-triyl)tris(4,4,5,5-tetramethyl-1,3,2-dioxaborolane)
1361598-50-6

2,2',2''-(ethane-1,1,2-triyl)tris(4,4,5,5-tetramethyl-1,3,2-dioxaborolane)

B

pinacol vinylboronate
75927-49-0

pinacol vinylboronate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: tetrahydrofuran / 2 h / -78 °C / Sealed tube; Inert atmosphere
2: tetrabutylammomium bromide; tris(2,2-bipyridine)ruthenium(II) hexafluorophosphate; potassium iodide / acetonitrile / 24 h / 20 °C / Inert atmosphere; Sealed tube; Irradiation
View Scheme
C14H27B2O4(1-)*BrMg(1+)

C14H27B2O4(1-)*BrMg(1+)

A

2,2',2''-(ethane-1,1,2-triyl)tris(4,4,5,5-tetramethyl-1,3,2-dioxaborolane)
1361598-50-6

2,2',2''-(ethane-1,1,2-triyl)tris(4,4,5,5-tetramethyl-1,3,2-dioxaborolane)

B

pinacol vinylboronate
75927-49-0

pinacol vinylboronate

Conditions
ConditionsYield
With tris(2,2-bipyridine)ruthenium(II) hexafluorophosphate; tetrabutylammomium bromide; potassium iodide In acetonitrile at 20℃; for 24h; Inert atmosphere; Sealed tube; Irradiation;
4-(1,1,1,3,3,3-hexafluoro-2-(methoxymethoxy)propan-2-yl)-1-(4-iodo-3-methylphenoxy)-2-n-propylbenzene
1198166-34-5

4-(1,1,1,3,3,3-hexafluoro-2-(methoxymethoxy)propan-2-yl)-1-(4-iodo-3-methylphenoxy)-2-n-propylbenzene

pinacol vinylboronate
75927-49-0

pinacol vinylboronate

4-(1,1,1,3,3,3-hexafluoro-2-(methoxymethoxy)propan-2-yl)-1-(3-methyl-4-vinylphenoxy)-2-propylbenzene
1198166-35-6

4-(1,1,1,3,3,3-hexafluoro-2-(methoxymethoxy)propan-2-yl)-1-(3-methyl-4-vinylphenoxy)-2-propylbenzene

Conditions
ConditionsYield
With sodium carbonate; tetrakis(triphenylphosphine) palladium(0) In water; N,N-dimethyl-formamide at 80℃; for 1h; Suzuki Coupling;100%
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In water; N,N-dimethyl-formamide at 80℃; Suzuki-Miyaura Coupling; Microwave irradiation;99%
9-bromo-N-(tert-butyl)-3,4-dihydro-2H,6H-pyrimido[1,2-c][1,3]benzothiazin-6-imine
1394235-81-4

9-bromo-N-(tert-butyl)-3,4-dihydro-2H,6H-pyrimido[1,2-c][1,3]benzothiazin-6-imine

pinacol vinylboronate
75927-49-0

pinacol vinylboronate

N-(tert-butyl)-3,4-dihydro-9-vinyl-2H,6H-pyrimido[1,2-c][1,3]benzothiazin-6-imine
1394235-92-7

N-(tert-butyl)-3,4-dihydro-9-vinyl-2H,6H-pyrimido[1,2-c][1,3]benzothiazin-6-imine

Conditions
ConditionsYield
With tetrakis(triphenylphosphine) palladium(0); dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium carbonate In ethanol; water; toluene for 1h; Suzuki coupling; Reflux;100%
1-[3-chloro-5-(trifluoromethyl)pyridin-2-yl]piperidin-2-one
1430092-25-3

1-[3-chloro-5-(trifluoromethyl)pyridin-2-yl]piperidin-2-one

pinacol vinylboronate
75927-49-0

pinacol vinylboronate

1-[5-(trifluoromethyl)-3-vinylpyridin-2-yl]piperidin-2-one
1430092-26-4

1-[5-(trifluoromethyl)-3-vinylpyridin-2-yl]piperidin-2-one

Conditions
ConditionsYield
With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; potassium phosphate; palladium diacetate In water; acetonitrile at 120℃; for 0.666667h;100%
2-(5-(3,4-dichloroquinolin-6-yl)pyrimidin-2-yl)propan-2-ol

2-(5-(3,4-dichloroquinolin-6-yl)pyrimidin-2-yl)propan-2-ol

pinacol vinylboronate
75927-49-0

pinacol vinylboronate

2-(5-(3-chloro-4-vinylquinolin-6-yl)pyrimidin-2-yl)propan-2-ol

2-(5-(3-chloro-4-vinylquinolin-6-yl)pyrimidin-2-yl)propan-2-ol

Conditions
ConditionsYield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In 1,4-dioxane at 90℃; for 20h; Suzuki-Miyaura Coupling; Inert atmosphere; Sealed tube;100%
2-bromonaphthalene
580-13-2

2-bromonaphthalene

pinacol vinylboronate
75927-49-0

pinacol vinylboronate

naphthyl vinyl boronic acid pinacol ester

naphthyl vinyl boronic acid pinacol ester

Conditions
ConditionsYield
With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; palladium diacetate; triethylamine In 1,4-dioxane at 80℃; for 24h; Sealed tube; Inert atmosphere;100%
ethyl 2-(2-(3-hydroxy-3-methylhex-5-en-1-yl)-1,3-dioxolan-2-yl)acetate

ethyl 2-(2-(3-hydroxy-3-methylhex-5-en-1-yl)-1,3-dioxolan-2-yl)acetate

pinacol vinylboronate
75927-49-0

pinacol vinylboronate

(E)-ethyl 2-(2-(3-hydroxy-3-methyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)hex-5-en-1-yl)-1,3-dioxolan-2-yl)acetate

(E)-ethyl 2-(2-(3-hydroxy-3-methyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)hex-5-en-1-yl)-1,3-dioxolan-2-yl)acetate

Conditions
ConditionsYield
With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride In dichloromethane at 120℃; for 0.333333h; Inert atmosphere; Microwave irradiation;100%
3-bromoisonicotinic acid
13959-02-9

3-bromoisonicotinic acid

pinacol vinylboronate
75927-49-0

pinacol vinylboronate

3-vinyl-4-picolinic acid

3-vinyl-4-picolinic acid

Conditions
ConditionsYield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In 1,4-dioxane; water at 100℃; Inert atmosphere;100%
isopropyl 6-(3-((benzyloxy)methyl)-4-ethyl-5-oxo-4,5-dihydro-1H-1,2,4-triazol-1-yl)-2-chloro-5-fluoronicotinate

isopropyl 6-(3-((benzyloxy)methyl)-4-ethyl-5-oxo-4,5-dihydro-1H-1,2,4-triazol-1-yl)-2-chloro-5-fluoronicotinate

pinacol vinylboronate
75927-49-0

pinacol vinylboronate

isopropyl 6-(3-((benzyloxy)methyl)-4-ethyl-5-oxo-4,5-dihydro-1H-1,2,4-triazol-1-yl)-5-fluoro-2-vinylnicotinate

isopropyl 6-(3-((benzyloxy)methyl)-4-ethyl-5-oxo-4,5-dihydro-1H-1,2,4-triazol-1-yl)-5-fluoro-2-vinylnicotinate

Conditions
ConditionsYield
With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; sodium carbonate In 1,4-dioxane; water at 100℃; Inert atmosphere;100%
2-bromo-5-methyl-N-[3-(trifluoromethyl)phenyl]pyridin-4-amine

2-bromo-5-methyl-N-[3-(trifluoromethyl)phenyl]pyridin-4-amine

pinacol vinylboronate
75927-49-0

pinacol vinylboronate

5-methyl-N-[3-(trifluoromethyl)phenyl]-2-vinyl-pyridin-4-amine

5-methyl-N-[3-(trifluoromethyl)phenyl]-2-vinyl-pyridin-4-amine

Conditions
ConditionsYield
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; caesium carbonate In 1,4-dioxane; water at 100℃; for 30h; Microwave irradiation;99.9%
methyl 6-bromo-3-[(tert-butoxycarbonyl)amino]thieno[3,2-b]pyridine-2-carboxylate

methyl 6-bromo-3-[(tert-butoxycarbonyl)amino]thieno[3,2-b]pyridine-2-carboxylate

pinacol vinylboronate
75927-49-0

pinacol vinylboronate

methyl 3-[(tert-butoxycarbonyl)amino]-6-vinylthieno[3,2-b]pyridine-2-carboxylate

methyl 3-[(tert-butoxycarbonyl)amino]-6-vinylthieno[3,2-b]pyridine-2-carboxylate

Conditions
ConditionsYield
With bis(tri-t-butylphosphine)palladium(0); N-ethyl-N,N-diisopropylamine In 1,4-dioxane; water at 130℃; for 0.666667h; Suzuki Coupling;99.6%
(R)-tert-butyl 4-(2-(2-bromo-4-nitrophenoxy)ethyl)-2-methylpiperazine-1-carboxylate

(R)-tert-butyl 4-(2-(2-bromo-4-nitrophenoxy)ethyl)-2-methylpiperazine-1-carboxylate

pinacol vinylboronate
75927-49-0

pinacol vinylboronate

(2R)-tert-butyl 2-methyl-4-(2-(4-nitro-2-vinylphenoxy)ethyl)piperazine-1-carboxylate

(2R)-tert-butyl 2-methyl-4-(2-(4-nitro-2-vinylphenoxy)ethyl)piperazine-1-carboxylate

Conditions
ConditionsYield
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride In 1,4-dioxane; water at 90℃; for 12h; Inert atmosphere;99.6%
3-bromo-4-(cyclohexylamino)-N-methylbenzenesulfonamide

3-bromo-4-(cyclohexylamino)-N-methylbenzenesulfonamide

pinacol vinylboronate
75927-49-0

pinacol vinylboronate

4-(cyclohexylamino)-N-methyl-3-vinylbenzenesulfonamide

4-(cyclohexylamino)-N-methyl-3-vinylbenzenesulfonamide

Conditions
ConditionsYield
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; caesium carbonate In 1,4-dioxane; water at 100℃; for 0.5h; Microwave irradiation;99.5%
ethyl 2-(3-bromo-4-(2-fluoro-4-hydroxy-3-isopropylbenzyl)-5-methylphenoxy)acetate

ethyl 2-(3-bromo-4-(2-fluoro-4-hydroxy-3-isopropylbenzyl)-5-methylphenoxy)acetate

pinacol vinylboronate
75927-49-0

pinacol vinylboronate

2-(4-(2-fluoro-4-hydroxy-3-isopropylbenzyl)-3-methyl-5-vinylphenoxy)acetic acid

2-(4-(2-fluoro-4-hydroxy-3-isopropylbenzyl)-3-methyl-5-vinylphenoxy)acetic acid

Conditions
ConditionsYield
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate In 1,4-dioxane; water at 120℃; for 2h; Microwave irradiation;99.4%
methyl 3-amino-6-bromothieno[3,2-b]pyridine-2-carboxylate
1206907-38-1

methyl 3-amino-6-bromothieno[3,2-b]pyridine-2-carboxylate

pinacol vinylboronate
75927-49-0

pinacol vinylboronate

methyl 3-amino-6-vinylthieno[3,2-b]pyridine-2-carboxylate

methyl 3-amino-6-vinylthieno[3,2-b]pyridine-2-carboxylate

Conditions
ConditionsYield
With bis(tri-t-butylphosphine)palladium(0); N-ethyl-N,N-diisopropylamine In 1,4-dioxane; water at 130℃; for 0.666667h; Suzuki Coupling;99.3%
trifluoro-methanesulfonic acid 2,6-dichloro-3,5-difluoro-phenyl ester
877400-00-5

trifluoro-methanesulfonic acid 2,6-dichloro-3,5-difluoro-phenyl ester

pinacol vinylboronate
75927-49-0

pinacol vinylboronate

C8H4Cl2F2
877400-02-7

C8H4Cl2F2

Conditions
ConditionsYield
With caesium carbonate; bis-triphenylphosphine-palladium(II) chloride In 1,2-dimethoxyethane; water at 70℃; for 15h;99%
4-[(4-bromo-1,3-thiazol-2-yl)methyl]morpholine
919347-47-0

4-[(4-bromo-1,3-thiazol-2-yl)methyl]morpholine

pinacol vinylboronate
75927-49-0

pinacol vinylboronate

(E)-4-((4-(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)vinyl)thiazol-2-yl)methyl)morpholine
1247003-29-7

(E)-4-((4-(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)vinyl)thiazol-2-yl)methyl)morpholine

Conditions
ConditionsYield
With triethylamine; bis(tri-t-butylphosphine)palladium(0) In N,N-dimethyl-formamide at 120℃; for 1h; Microwave irradiation;99%
4-(4-bromophenoxy)-1-isopropylpiperidine
1373010-28-6

4-(4-bromophenoxy)-1-isopropylpiperidine

pinacol vinylboronate
75927-49-0

pinacol vinylboronate

(E)-1-isopropyl-4-(4-(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)vinyl)phenoxy)piperidine
1373010-27-5

(E)-1-isopropyl-4-(4-(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)vinyl)phenoxy)piperidine

Conditions
ConditionsYield
With triethylamine; bis(tri-t-butylphosphine)palladium(0) In toluene at 80℃; for 2h; Inert atmosphere;99%
With bis(tri-t-butylphosphine)palladium(0); triethylamine In toluene at 20 - 80℃; Inert atmosphere;99%
4-(4-bromophenoxy)-1-methylpiperidine

4-(4-bromophenoxy)-1-methylpiperidine

pinacol vinylboronate
75927-49-0

pinacol vinylboronate

(E)-1-methyl-4-(4-(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)vinyl)phenoxy)piperidine
1247003-32-2

(E)-1-methyl-4-(4-(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)vinyl)phenoxy)piperidine

Conditions
ConditionsYield
With bis(tri-t-butylphosphine)palladium(0); triethylamine In toluene at 20 - 80℃; Inert atmosphere;99%
7-Bromo-4-methoxybenzoxazole

7-Bromo-4-methoxybenzoxazole

pinacol vinylboronate
75927-49-0

pinacol vinylboronate

4-methoxy-7-vinylbenzo[d]oxazole

4-methoxy-7-vinylbenzo[d]oxazole

Conditions
ConditionsYield
With potassium phosphate; palladium diacetate; CyJohnPhos In 1,4-dioxane; water Inert atmosphere; Reflux;99%
C16H24BrClF2OSi

C16H24BrClF2OSi

pinacol vinylboronate
75927-49-0

pinacol vinylboronate

C18H27ClF2OSi

C18H27ClF2OSi

Conditions
ConditionsYield
With potassium phosphate; palladium diacetate; triphenylphosphine In toluene at 95℃; for 14h; Suzuki Coupling; Inert atmosphere;99%
Stage #1: pinacol vinylboronate With potassium phosphate In toluene at 20℃; for 0.166667h;
Stage #2: C16H24BrClF2OSi With palladium diacetate; triphenylphosphine In toluene at 95℃; for 14h; Inert atmosphere;
99%
tert-butyl 2-chloro-4-(4-fluoro-2-(trifluoromethyl)phenoxy)-5,8-dihydropyrido[3,4-d]pyrimidine-7(6H)-carboxylate

tert-butyl 2-chloro-4-(4-fluoro-2-(trifluoromethyl)phenoxy)-5,8-dihydropyrido[3,4-d]pyrimidine-7(6H)-carboxylate

pinacol vinylboronate
75927-49-0

pinacol vinylboronate

tert-butyl 4-(4-fluoro-2-(trifluoromethyl)phenoxy)-2-vinyl-5,8-dihydropyrido[3,4-d]pyrimidine-7(6H)-carboxylate

tert-butyl 4-(4-fluoro-2-(trifluoromethyl)phenoxy)-2-vinyl-5,8-dihydropyrido[3,4-d]pyrimidine-7(6H)-carboxylate

Conditions
ConditionsYield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In 1,4-dioxane; water at 95℃; for 2h; Inert atmosphere;99%
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In 1,4-dioxane; water at 95℃; for 2h; Inert atmosphere;99%
4-chloro-5-iodo-7-(1-methylcyclopropyl)-7H-pyrrolo[2,3-d]pyrimidine

4-chloro-5-iodo-7-(1-methylcyclopropyl)-7H-pyrrolo[2,3-d]pyrimidine

pinacol vinylboronate
75927-49-0

pinacol vinylboronate

4-chloro-7-(1-methylcyclopropyl)-5-vinyl-7H-pyrrolo[2,3-d]pyrimidine

4-chloro-7-(1-methylcyclopropyl)-5-vinyl-7H-pyrrolo[2,3-d]pyrimidine

Conditions
ConditionsYield
With potassium phosphate; tetrakis(triphenylphosphine) palladium(0) In 1,4-dioxane; water at 90℃; for 3h; Inert atmosphere;99%
pinacol vinylboronate
75927-49-0

pinacol vinylboronate

N-Benzyl-2-iodo-N-(2-methyl-allyl)-benzamide

N-Benzyl-2-iodo-N-(2-methyl-allyl)-benzamide

A

(R)-4-allyl-2-benzyl-4-methyl-3,4-dihydroisoquinolin-1(2H)-one

(R)-4-allyl-2-benzyl-4-methyl-3,4-dihydroisoquinolin-1(2H)-one

B

4-allyl-2-benzyl-4-methyl-3,4-dihydroisoquinolin-1(2H)-one

4-allyl-2-benzyl-4-methyl-3,4-dihydroisoquinolin-1(2H)-one

Conditions
ConditionsYield
With tris(dibenzylideneacetone)dipalladium(0) chloroform complex; (R)-N-((S)-(3,5-di-tert-butyl-4-methoxyphenyl)(2-(dicyclohexylphosphanyl)phenyl)methyl)-N,2-dimethylpropane-2-sulfinamide; caesium carbonate In toluene at 60℃; for 60h; Inert atmosphere;A 99%
B n/a
With tris(dibenzylideneacetone)dipalladium(0) chloroform complex; (R)-N-((S)-(3,5-di-tert-butyl-4-methoxyphenyl)(2-(dicyclohexylphosphanyl)phenyl)methyl)-N,2-dimethylpropane-2-sulfinamide; caesium carbonate In toluene at 60℃; for 60h; Sealed tube; Inert atmosphere; Overall yield = 99 percent; Overall yield = 62.9 mg; enantioselective reaction;A n/a
B n/a
ethyl 2-chloro-4-methyl-3-pyridinecarboxylate
50840-02-3

ethyl 2-chloro-4-methyl-3-pyridinecarboxylate

pinacol vinylboronate
75927-49-0

pinacol vinylboronate

ethyl 2-ethenyl-4-methylpyridine-3-carboxylate

ethyl 2-ethenyl-4-methylpyridine-3-carboxylate

Conditions
ConditionsYield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In 1,4-dioxane; water at 90℃; for 16h; Inert atmosphere;98.7%
4-tolyl iodide
624-31-7

4-tolyl iodide

pinacol vinylboronate
75927-49-0

pinacol vinylboronate

2-[(E)-2-p-tolylethenyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
149777-84-4

2-[(E)-2-p-tolylethenyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Conditions
ConditionsYield
With bis(tri-t-butylphosphine)palladium(0); triethylamine In toluene at 50℃; for 5h;98%

75927-49-0Relevant articles and documents

An Olefinic 1,2-Boryl-Migration Enabled by Radical Addition: Construction of gem-Bis(boryl)alkanes

Zhao, Binlin,Li, Zexian,Wu, Yixiao,Wang, Yandong,Qian, Jiasheng,Yuan, Yu,Shi, Zhuangzhi

supporting information, p. 9448 - 9452 (2019/08/07)

A series of in situ formed alkenyl diboronate complexes from alkenyl Grignard reagents (commercially available or prepared from alkenyl bromides and Mg) with B2Pin2 (bis(pinacolato)diboron) react with diverse alkyl halides by a Ru photocatalyst to give various gem-bis(boryl)alkanes. Alkyl radicals add efficiently to the alkenyl diboronate complexes, and the adduct radical anions undergo radical-polar crossover, specifically, a 1,2-boryl-anion shift from boron to the α-carbon sp2 center. This transformation shows good functional-group compatibility and can serve as a powerful synthetic tool for late-stage functionalization in complex compounds. Measurements of the quantum yield reveal that a radical-chain mechanism is operative in which the alkenyl diboronates acts as reductive quencher for the excited state of the photocatalyst.

Synthesis of functionalized vinyl boronates via ruthenium-catalyzed olefin cross-metathesis and subsequent conversion to vinyl halides

Morrill, Christie,Grubbs, Robert H.

, p. 6031 - 6034 (2007/10/03)

Functionalized vinyl pinacol boronates suitable for Suzuki cross-coupling reactions are synthesized using ruthenium-catalyzed olefin cross-metathesis of 1-propenyl pinacol boronate and various alkenes, including functionalized and 1,1-disubstituted alkenes. The resultant boronate cross products are stereoselectively transformed into predominantly Z-vinyl bromides and E-vinyl iodides. The vinyl bromides may be synthesized in a two-step, one-pot synthesis from a variety of olefins, resulting in a Z-selective formal vinyl bromide cross-metathesis reaction.

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