73183-34-3

Basic information

• Product Name: Bis(pinacolato)diboron
• Synonyms: BIS(2,2,3,3-TETRAMETHYL-2,3-BUTANEDIONATO)DIBORON;BIS(PINACOLATO)DIBORANE;BIS(PINACOLATO)DIBORON;DIBORON PINACOL ESTER;4,4,4',4',5,5,5',5'-OCTAMETHYL-2,2'-BL-1,3,2-DIOXABOROLANE;4,4,4',4',5,5,5',5'-OCTAMETHYL-2,2'-BIS(1,3,2-DIOXABOROLANE);4,4,4',4',5,5,5',5'-OCTAMETHYL-2,2'-BI-1,3,2-DIOXABOROLANE;4,4,4',4',5,5,5',5'-OCTAMETHYL-2,2-BI-1,3,2-DIOXABOROLANE
• CAS NO: 73183-34-3
• Molecular Formula: C₁₂H₂₄B₂O₄
• Molecular Weight: 253.93856
• EINECS: -0
• Product Categories: Pharmaceutical Intermediates;Boron Compounds;blocks;BoronicAcids;Miscellaneous;Small molecule;Aliphatics;Boronic Acids & Esters;DIBORON SERIES;Reagent;Organoborons;Diboron Esters;B (Classes of Boron Compounds);CHIRAL CHEMICALS;Boronic Acids & Esters;OLED materials,pharm chemical,electronic
• Mol File: 73183-34-3.mol
• Article Data: 34

Chemical Properties

• Melting Point: 137-140 °C(lit.)
• Boiling Point: 222.595 °C at 760 mmHg
• Flash Point: 88.423 °C
• Appearance: White/Powder or Platelets
• Density: 0.98
• Vapor Pressure: 0.15mmHg at 25°C
• Refractive Index: 1.432
• Storage Temp.: 0-6°C
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• Water Solubility: Soluble in tetrahydrofuran, dichloromethane, toluene, hexane and heptane. Insoluble in water.
• Sensitive: moisture sensitive
• Merck: 14,1300
• BRN: 7703552
• CAS DataBase Reference: Bis(pinacolato)diboron(CAS DataBase Reference)
• NIST Chemistry Reference: Bis(pinacolato)diboron(73183-34-3)
• EPA Substance Registry System: Bis(pinacolato)diboron(73183-34-3)

Safety Data

• Hazard Codes: Xi,Xn
• Statements: 36/37/38-20/21/22
• Safety Statements: 26-37/39-36-24/25
• WGK Germany: 3
• TSCA: No
• HazardClass: IRRITANT, IRRITANT-HARMFUL, KEEP
• Hazardous Substances Data: 73183-34-3(Hazardous Substances Data)

Usage

Definition

Bis(pinacolato)diboron is a covalent compound containing two boron atoms and two pinacolato ligands. It has the formula [(CH3)4C2O2B]2; the pinacol groups are sometimes abbreviated as "pin", so the structure is sometimes represented as B2pin2.

Uses

Different sources of media describe the Uses of 73183-34-3 differently. You can refer to the following data:
1. It is a colourless solid that is soluble in organic solvents. It is a commercially available reagent for making pinacol boronic esters for organic synthesis. Unlike some other diboron compounds, B2pin2 is not moisture-sensitive and can be handled in air.
2. suzuki reaction
3. Bis(pinacolato)diboron is used as a condensation agent in the preparation poly(arylene)s. Bis(pinacolato)diboron is an organoboranate with potential use as matrix metallo-proteinase (MMP-2) inhibitor.
4. As a boron source in Pt-mediated diborations, coupling reactions; in Rh-or Ir-mediated borylations of alkanes and arenes, and in carbenoid chemistry.

Reaction

Reagent used for the synthesis of aryl, alkenyl, allyl and alkylboronic esters. Reagent used for the borylation of an α,β-unsaturated ketones. Reagent used for the synthesis of precursors for conducting polymers. Reagent used for the synthesis of in vivo fluorescent probes. Reagent used for the diborylation of alkynes.

Preparation

Bis(pinacolato)diboron may be prepared by reacting tetrakis(dimethylamino)diboron with pinacol in acidic conditions.?The B-B bond length is 1.711(6) ?. The B-B bond adds across alkenes and alkynes to give the 1,2-diborylated alkanes and alkenes. Using various organorhodium or organoiridium catalysts, it can also be installed onto saturated hydrocarbons: CH3(CH2)6CH3 + [pinB]2 → pinBH + CH3(CH2)7Bpin These reactions proceed via boryl complexes.

Suzuki reaction

In the Suzuki reaction, Bis (pinacolato) diboron has the advantages of high reaction selectivity, mild conditions, and high yield. For some compounds that are unstable or need to improve the selectivity of the reaction, Bis (pinacolato) diboron and aryl halide are used. React is a good choice.

Chemical Properties

Bis(pinacolato)diboron is a white crystal powder, It is commonly used coupling reagent.

General Description

Bis(pinacolato)diboron or (B2pin2) is the most commonly used diborane reagent in organic synthesis due to its high stability in air and moisture. It can be synthesized by treating tetrakis(dimethylamino)diboron with pinacol in acidic conditions.

InChI:InChI=1/C12H24B2O4/c1-9(2)10(3,4)16-13(15-9)14-17-11(5,6)12(7,8)18-14/h1-8H3

Synthetic route

2,3-dimethyl-2,3-butane diol (76-09-5) → bis(pinacol)diborane (73183-34-3)

Conditions	Yield
With tetrakis(dimethylamido)diborane In diethyl ether at 20℃; for 18h; Conversion of starting material;	100%
With tetrakis(dimethylamido)diborane at 50 - 100℃; for 0.616667h; Conversion of starting material;	94.2%
With tetrakis(dimethylamido)diborane In n-heptane at 40 - 98℃; for 0.6h; Conversion of starting material;	90.5%

C18H29B2O4(1-)*Li(1+)*0.125C12H24B2O4 + tris(pentafluorophenyl)borate (1109-15-5) + 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane (25015-63-8) → Li[(hydride)B(pentafluorophenyl)3] + 2-phenyl-4,4,5,5-tetramethyl-1,3,2-dioxoborole (24388-23-6) + bis(pinacol)diborane (73183-34-3)

Conditions	Yield
at 20℃; for 12h;	A 73% B 80% C 41%

2,3-dimethyl-2,3-butane diol (76-09-5) + tetrakis(dimethylamido)diborane (1630-79-1) → bis(pinacol)diborane (73183-34-3)

Conditions	Yield
With hydrogenchloride In diethyl ether; toluene at 20℃; for 4h; Inert atmosphere; Cooling with ice;	79%
In diethyl ether N2-atmosphere; addn. of 2 equiv. diol to B-compd., stirring for at room temp. for 5 h; cooling to -78°C, addn. of excess 1 M HCl in Et2O, slow warming to room temp., solvent removal (vac.), extn. into hexane, filtration (Celite), solvent removal (vac.); elem. anal.;	76%
In benzene dropwise addn. of pinakol in benzene to a soln. of B2(NMe2)4 in benzeneunder N2 (stirring), addn. of a 2.7 M HCl soln. in ether, stirring (4 h); fritting from insolubles, evapn. of solvent (vac.), recrystn. (pentane); elem. anal.;	71%
With potassium acetate In toluene at 80℃; for 2h;

cis-[Ir(4,4'-di-tert-butyl-2,2'-bipyridine)2(C8H12)(BO2C2(CH3)4)2][CF3SO3] → (C5H3N(C(CH3)3))2Ir(C8H12)(1+)*CF3SO3(1-)=[(C5H3N(C(CH3)3))2Ir(C8H12)][CF3SO3] (401797-12-4) + bis(pinacol)diborane (73183-34-3)

Conditions	Yield
In benzene-d6 at 80°C;	A n/a B 75%

C18H29B2O4(1-)*Li(1+)*0.125C12H24B2O4 + tris(pentafluorophenyl)borate (1109-15-5) → Li[(hydride)B(pentafluorophenyl)3] + 2-phenyl-4,4,5,5-tetramethyl-1,3,2-dioxoborole (24388-23-6) + bis(pinacol)diborane (73183-34-3)

Conditions	Yield
With hydrogen at 20℃; under 3000.3 Torr; for 12h;	A 71% B 73% C 52%

2,3-dimethyl-2,3-butane diol (76-09-5) + tetrakis(tetrahydropyrrole)boron (158752-98-8) → bis(pinacol)diborane (73183-34-3)

Conditions	Yield
In toluene at 90 - 100℃; Inert atmosphere; Autoclave; Large scale;	69%

ethene (74-85-1) + C18H29B2O4(1-)*Li(1+)*0.125C12H24B2O4 + tris(pentafluorophenyl)borate (1109-15-5) → C26H16B2F15O2(1-)*Li(1+) + 2-phenyl-4,4,5,5-tetramethyl-1,3,2-dioxoborole (24388-23-6) + bis(pinacol)diborane (73183-34-3)

Conditions	Yield
at 20℃; under 45004.5 Torr; for 12h;	A 64% B n/a C n/a

4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane (25015-63-8) → bis(pinacol)diborane (73183-34-3)

Conditions	Yield
With C25H36FeN2Si for 10h; Inert atmosphere; Reflux;	62%
With C3H10B(1-)*K(1+) In neat (no solvent) at 25℃; for 16h; Inert atmosphere; Schlenk technique;	44%
With platinum on aluminium oxide for 48h; Heating;
With catalyst: Rh or Pd or Pt on alumina In not given Soxlet reactor, HBPin distilled in presence of catalyst: Rh/alumina for 20 h or Pd/alumina for 40 h or Pt/alumina for 20 h;
With carbonylhydrido[6-(di-tert-butylphosphinomethylene)-2-(N,N-diethylaminomethyl)-1,6-dihydropyridine]ruthenium(II) In tetrahydrofuran; 1,4-dioxane for 18h; Reflux;	10 %Chromat.

2,3-dimethyl-2,3-butane diol (76-09-5) + 2,2'-bis(1,3,2-benzodioxaborole) (13826-27-2) + tert-butyl 4-(((methylthio)carbonothioyl)oxy)piperidine-1-carboxylate (1612172-49-2) → 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)piperidine-1-carboxylic acid tert-butyl ester (1048970-17-7) + bis(pinacol)diborane (73183-34-3)

Conditions

Yield

Stage #1: 2,2'-bis(1,3,2-benzodioxaborole); tert-butyl 4-(((methylthio)carbonothioyl)oxy)piperidine-1-carboxylate With 2,2'-azobis(isobutyronitrile); tris-(trimethylsilyl)silane In N,N-dimethyl acetamide for 24h; Inert atmosphere; Schlenk technique; Irradiation; Stage #2: 2,3-dimethyl-2,3-butane diol With triethylamine In N,N-dimethyl acetamide for 2h; Inert atmosphere; Schlenk technique; Irradiation;

A 58% B 17%

2-phenyl-4,4,5,5-tetramethyl-1,3,2-dioxoborole (24388-23-6) + para-chlorobenzoic acid (74-11-3) → biphenyl (92-52-4) + pinacolboronic acid (25240-59-9) + bis(pinacol)diborane (73183-34-3) + biphenyl-4-carboxylic acid (92-92-2)

Conditions	Yield
With water In water-d2 at 27℃; for 24h; Inert atmosphere;	A 49% B n/a C n/a D 50%

2,3-dimethyl-2,3-butane diol (76-09-5) + 4-tert-Butylcatechol (98-29-3) + boron trichloride (10294-34-5) → bis(pinacol)diborane (73183-34-3)

Conditions	Yield
With sodium amalgam; lithium dimethylamide In n-heptane; pentane under inert atm. to soln. BCl3 in heptane at 0°C soln. catechol in pentane was added, stirred 0.5 h at 0°C and 1 h at room temp., solvent was evapd, residue was dissolved in toluene, Na/Hg amalgam was adde and heated at 90°C for 6 h; soln. was filtered, pinacol was added, soln. was stirred at room temp. for 1 h, solvent was evapd., Et2O was added, LiNMe2 in Et2O was added slowly, solvent was evapd., chromy. on alumina;	46%
With sodium amalgam; lithium dimethylamide In n-heptane; pentane under inert atm. to soln. BCl3 in heptane at 0°C soln. catechol in pentane was added, stirred 0.5 h at 0°C and 1 h at room temp., solvent was evapd, residue was dissolved in toluene, Na/Hg amalgam was adde and heated at 90°C for 6 h; soln. was filtered, pinacol was added, soln. was stirred at room temp. for 1 h, solvent was evapd., Et2O was added, LiNMe2 in Et2O was added slowly, solvent was evapd., residue was extd. with pentane, concd., and crystd. at -35°C;	32%

C42H50Mg2N4 + 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane (25015-63-8) → C54H74B2Mg2N4O6 + C54H78B2Mg2N4O4 + bis(pinacol)diborane (73183-34-3)

Conditions	Yield
In toluene at -78 - 20℃; Inert atmosphere; Schlenk technique;	A 5% B 27% C 18 mg

2,3-dimethyl-2,3-butane diol (76-09-5) + 3,5-Di-tert-butylcatechol (1020-31-1) + boron trichloride (10294-34-5) → bis(pinacol)diborane (73183-34-3)

Conditions

Yield

With sodium amalgam In n-heptane; pentane under inert atm. to soln. BCl3 in heptane at 0°C soln. catechol in pentane was added, stirred 0.5 h at 0°C and 1 h at room temp., solvent was evapd, residue was dissolved in toluene, Na/Hg amalgam was adde and heated at 90°C for 6 h; soln. was filtered, pinacol was added, soln. was stirred at room temp. for 1 h, soln. was concd., layered with pentane and cooled to -35°C;

23%

4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane (25015-63-8) + benzene (71-43-2) → 2-phenyl-4,4,5,5-tetramethyl-1,3,2-dioxoborole (24388-23-6) + bis(pinacol)diborane (73183-34-3)

Conditions	Yield
trans-chloro(dinitrogen)bis(tri-isopropylphosphine)rhodium(I) In benzene 1 M or 1/3 M soln. heated at 140°C for 58 h; various condns. various yield;	A 20% B 7%

B2((OC(C(2)H3)2)2)2 + [Ir(4,4-di-tert-butylbipyridine)(cyclooctene)(4,4,5,5-tetramethyl-1,3,2-dioxaborolanyl)3] → ((2)H3C)4C2O2BBO2C2(CH3)4 + bis(pinacol)diborane (73183-34-3)

Conditions	Yield
In Cyclohexane-d12 at 25℃; Kinetics; Further Variations:; Temperatures;

1,2-B2(NMe2)2(catecholate) (269742-02-1) + 2,3-dimethyl-2,3-butane diol (76-09-5) → 1,1-B2(pinacolate)(catecholate) + 2,2'-bis(1,3,2-benzodioxaborole) (13826-27-2) + bis(pinacol)diborane (73183-34-3)

Conditions	Yield
In tetrahydrofuran at -78℃;
With HCl In tetrahydrofuran; diethyl ether pinacol and slight excess of HCl in diethylether added to (C6H4O2)B2(N(CH3)2)2 (generated in situ in THF) at -78°C; filtered, volatiles removed from filtrate, extraction with hexane, subsequent extraction with benzene yields B2(catecholate)2;

2,3-dimethyl-2,3-butane diol (76-09-5) + cis-[Pt(difluoroboryl)2(PPh3)2] (203259-76-1) → tris(triphenylphosphine)platinum(0) (13517-35-6) + (triphenylphosphine)2PtHCl (25879-12-3, 16841-99-9, 16902-93-5) + bis(pinacol)diborane (73183-34-3)

Conditions	Yield
With 1,8-diazabicyclo[5.4.0]undec-7-ene In dichloromethane under inert atmosphere, standard Schlenk and vac. line techniques; react. between Pt complex and pinacol in the presence of DBU in CH2Cl2; monitored by NMR spectroscopy;

dichlorobis(dimethylamino)diborane(4) (64541-76-0) + disodium pinacolate → tetrakis(dimethylamido)diborane (1630-79-1) + 1,1-B2(NMe2)2(pinacolate) + bis(pinacol)diborane (73183-34-3)

Conditions	Yield
In not given tetrachlorocatechol added to (C6H4O2)B2(N(CH3)2)2 generated in toluene, volatiles removed, residue dissolved in (C2H5)2O, HCl added;

2-{bis(dimethylamino)boryl}-1,3,2-benzodithiaborole (78336-54-6) + 2,2'-bis(1,3,2-benzodioxaborole) (13826-27-2) → 1,1-B2(dithiocatecholate)(catecholate) + bis(pinacol)diborane (73183-34-3) + 2,2'bi-1,3,2-benzodithiaborole (78336-55-7)

Conditions	Yield
With HCl In tetrahydrofuran

2-{bis(dimethylamino)boryl}-1,3,2-benzodithiaborole (78336-54-6) + 2,3-dimethyl-2,3-butane diol (76-09-5) → 1,1-B2(diethiocatecholate)(pinacolate) + bis(pinacol)diborane (73183-34-3) + 2,2'bi-1,3,2-benzodithiaborole (78336-55-7)

Conditions	Yield
With HCl In tetrahydrofuran

B2((OC(C(2)H3)2)2)2 + [Ir(4,4'-di-tert-butyl-2,2'-bipyridine)(cyclooctene)(4,4,5,5-tetramethyl-1,3,2-dioxaborolane)3] → ((2)H3C)4C2O2BBO2C2(CH3)4 + bis(pinacol)diborane (73183-34-3)

Conditions	Yield
In Cyclohexane-d12 Kinetics; (Schlenk; N2 atm.) complex was added to a soln. of boryl-compound in cyclohexane-d12 at -30°C (NMR tube), heated to 0°C, heated to40°C; not sepd., detected by NMR spectra;

2,3-dimethyl-2,3-butane diol (76-09-5) + tetrahydroxydiboron (13675-18-8) → bis(pinacol)diborane (73183-34-3)

Conditions	Yield
With potassium acetate at 80℃;

pinacolborane → bis(pinacol)diborane (73183-34-3)

Conditions	Yield
With Pt/Al2O3; triethylamine In 1,3,5-trimethyl-benzene at 120℃; Reagent/catalyst;	1.36 g

C61H58BO2P3PdSi + 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane (25015-63-8) → C61H58BO2P3PdSi + C55H47P3PdSi (1198806-66-4) + bis(pinacol)diborane (73183-34-3)

Conditions	Yield
In benzene-d6 at 29.84℃; for 1h; Inert atmosphere;	A n/a B n/a C 65 %Chromat.

C61H58BO2P3PdSi + 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane (25015-63-8) → C61H58BO2P3PdSi + C55H47P3PdSi (1198806-66-4) + bis(pinacol)diborane (73183-34-3)

Conditions	Yield
In benzene-d6 at 29.84℃; for 1h; Inert atmosphere;	A n/a B n/a C 17 %Chromat.

C61H58BO2P3PdSi + 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane (25015-63-8) → C55H47P3PdSi (1198806-66-4) + bis(pinacol)diborane (73183-34-3)

Conditions	Yield
In benzene-d6 at 24.84℃; for 48h; Equilibrium constant; Inert atmosphere;	A 30 %Spectr. B n/a

C46H52BO2P3PdSi + 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane (25015-63-8) → C40H41P3PdSi (1420041-82-2) + bis(pinacol)diborane (73183-34-3)

Conditions	Yield
In benzene-d6 at 24.84℃; for 24h; Equilibrium constant; Inert atmosphere;	A 17 %Spectr. B n/a

dimethylphenyl(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)silane (185990-03-8) → dimethyl(phenyl)((4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)oxy)silane (1349697-23-9) + dimethylphenylsilanol (5272-18-4) + 1,1,3,3-tetramethyl-1,3-diphenyldisiloxane (56-33-7) + bis(pinacol)diborane (73183-34-3)

Conditions	Yield
With Au-TiO2 In dichloromethane at 25℃; for 2h;

2,3-dimethyl-2,3-butane diol (76-09-5) + tetrakis(dimethylamido)diborane (1630-79-1) + N,N'-dimethyl-1,2-phenylenediamine (3213-79-4) → 1,1-B2(1,2-(NMe)2C6H4)2 (1357843-94-7) + pinB-Bdmab (1613645-10-5) + bis(pinacol)diborane (73183-34-3)

Conditions	Yield
With hydrogenchloride In diethyl ether; dichloromethane at -5 - 20℃; for 72h; Inert atmosphere; Schlenk technique;

2,3-dimethyl-2,3-butane diol (76-09-5) + 2-[(1E)-but-1-en-1-yl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (1301680-12-5) + B2(cat)2 → (R)-2,2',2''-(butane-1,1,2-triyl)tris(4,4,5,5-tetramethyl-1,3,2-dioxaborolane) + bis(pinacol)diborane (73183-34-3)

Conditions

Yield

Stage #1: 2-[(1E)-but-1-en-1-yl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane; B2(cat)2 With [Pt(1,5-diphenylpenta-1,4-dien-3-one)3]; (3aR,8aR)-4,4,8,8-tetrakis(3,5-diisopropylphenyl)-2,2-dimethyl-6-phenyltetrahydro-[1,3]dioxolo[4,5-e][1,3,2]dioxaphosphepine In tetrahydrofuran at 70℃; for 24h; Inert atmosphere; Sealed tube; Stage #2: 2,3-dimethyl-2,3-butane diol In tetrahydrofuran at 20℃; for 14h; Inert atmosphere; Sealed tube; Overall yield = 77 %; Overall yield = 1.46 g;

A 24.3 mg B n/a

1,3-dibromo-5-t-butylbenzene (129316-09-2) + bis(pinacol)diborane (73183-34-3) → 2,2'-(5-(tert-butyl)-1,3-phenylene)bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane)

Conditions	Yield
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate In N,N-dimethyl-formamide at 100℃; for 4h; Inert atmosphere;	100%
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate In 1,4-dioxane at 100℃; for 12h; Inert atmosphere;	63%
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate In 1,4-dioxane at 100℃; for 12h; Inert atmosphere;	63%
With potassium acetate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride In N,N-dimethyl-formamide at 80℃; for 11h; Substitution;	55%

4-Trifluoromethanesulfonyloxy-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester (138647-49-1) + bis(pinacol)diborane (73183-34-3) → tert-Butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3,6-dihydro-1(2H)-pyridinecarboxylate (375853-82-0, 286961-14-6)

Conditions	Yield
With 1,1'-bis(diphenylphosphino)ferrocene; potassium acetate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride at 80℃;	100%
With 1,1'-bis-(diphenylphosphino)ferrocene; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate In 1,4-dioxane at 80℃;	100%
With 1,1'-bis-(diphenylphosphino)ferrocene; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate In 1,4-dioxane at 80℃; Inert atmosphere;	100%

norborn-2-ene (498-66-8) + bis(pinacol)diborane (73183-34-3) → 4,4,5,5-Tetramethyl-2-[3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)bicyclo[2.2.1]hept-2-yl]-1,3,2-dioxaborolane

Conditions	Yield
With tris(bicyclo[2.2.1]heptene)palladium; triphenylphosphine at 20℃; for 2h;	100%

4-Octyne (1942-45-6) + bis(pinacol)diborane (73183-34-3) → (Z)-4,5-bis[(4’,4’,5’,5’-tetramethyl-[1’,3’,2’]-dioxaborolan-2’-yl)]oct-4-ene

Conditions	Yield
With tris(bicyclo[2.2.1]heptene)palladium; triphenylphosphine at 20℃; for 9h;	100%
With tetrakis(triphenylphosphine)platinum In N,N-dimethyl-formamide at 80℃; for 12h; Inert atmosphere;	98%
tetrakis(triphenylphosphine)platinum In N,N-dimethyl-formamide for 12h; Heating;	95%

1-Heptyne (628-71-7) + bis(pinacol)diborane (73183-34-3) → (E)-2,2′-(hept-1-ene-1,2-diyl)bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane)

Conditions	Yield
With tris(bicyclo[2.2.1]heptene)palladium; triphenylphosphine at 20℃; for 12h;	100%
With gold nanoparticles supported on titanium dioxide at 65℃; for 2h; chemoselective reaction;	91%
With methanol; potassium carbonate In diethyl ether at 40℃; for 12h; Inert atmosphere; chemoselective reaction;	72%

1,2-bis(4-methylphenyl)acetylene (2789-88-0) + bis(pinacol)diborane (73183-34-3) → (Z)-(4-Me-C6H4)C(B(OC(CH3)2C(CH3)2O))=C(4-Me-C6H4)(B(OC(CH3)2C(CH3)2O))

Conditions	Yield
With tris(bicyclo[2.2.1]heptene)palladium; triphenylphosphine at 20℃; for 5h;	100%
ethylenebis(triphenylphosphine)platinum(0) In toluene N2-atmosphere; 80°C (3 h); evapn. (vac.); detd. by GC / MS and NMR spectroscopy;
cis-[(PPh3)2Pt(B(1,2-O2-4-tBuC6H3))2] In toluene N2-atmosphere; 80°C (3 h); evapn. (vac.); detd. by GC / MS and NMR spectroscopy;
With tetrakis(triphenylphosphine)platinum In N,N-dimethyl-formamide at 80℃;

4,4'-dimethoxydiphenylacetylene (2132-62-9) + bis(pinacol)diborane (73183-34-3) → (Z)-1,2-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,2-bis(4-methoxyphenyl)ethene (178106-74-6)

Conditions	Yield
With tris(bicyclo[2.2.1]heptene)palladium; triphenylphosphine at 20℃; for 5.5h;	100%
With copper diacetate; tricyclohexylphosphine In toluene at 80℃; for 16h; Inert atmosphere;	76%
With tetrakis(triphenylphosphine)platinum In toluene at 110℃; for 24h; Inert atmosphere;	50%

4-methoxyphenylacetylen (768-60-5) + bis(pinacol)diborane (73183-34-3) → (E)-2,2'-(1-(4-methoxyphenyl)ethene-1,2-diyl)bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane)

Conditions	Yield
With tris(bicyclo[2.2.1]heptene)palladium; triphenylphosphine at 20℃; for 1.3h;	100%
With atomically dispersed Pt on beta-cyclodextrin-containing polymer In toluene at 100℃; for 2h;	90%
With Pd(1,3,4,5-tetramethylimidazol-2-ylidene)2(diphenylacetylene) In benzene at 20℃; for 4h; stereoselective reaction;	88%

bis(pinacol)diborane (73183-34-3) + 1,2-bis(4-(trifluoromethyl)phenyl)ethyne (119757-51-6) → CF3C6H4C(BO2C2(CH3)4)C(BO2C2(CH3)4)C6H4CF3 (355012-35-0)

Conditions	Yield
With tris(norbornene)platinum(0); Diphenyl-o-tolylphosphin In toluene at 20℃; for 4.3h; Product distribution; Kinetics; Further Variations:; Reagents; Solvents;	100%
With platinum-based catalyst Inert atmosphere;

1,2-dichloro-benzene (95-50-1) + bis(pinacol)diborane (73183-34-3) → 2-(3,4-dichlorophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (401797-02-2)

Conditions	Yield
With [Ir(COD)(OMe)]2-Covalent organic framework (4-iPr) In n-heptane at 100℃; for 24h; Inert atmosphere;	100%
Stage #1: bis(pinacol)diborane With C24H28ClIrN2O In n-heptane; isopropyl alcohol at 75℃; for 1h; Sealed tube; Cooling with liquid nitrogen; Inert atmosphere; Stage #2: 1,2-dichloro-benzene In n-heptane; isopropyl alcohol at 75℃; for 18h; Catalytic behavior; Sealed tube; Inert atmosphere;	97%
With [Ir(OMe)(1,5-cyclooctadiene)]2; C88H164N2 In n-heptane at 25℃; for 18h; Reagent/catalyst; Inert atmosphere;	95%

bis(pinacol)diborane (73183-34-3) + benzene (71-43-2) → 2-phenyl-4,4,5,5-tetramethyl-1,3,2-dioxoborole (24388-23-6)

Conditions	Yield
With [Ir(COD)(OMe)]2-Covalent organic framework (4-iPr) at 100℃; for 24h; Reagent/catalyst; Inert atmosphere;	100%
With iridium-1,5-cyclooctadiene complex immobilized 2,2'-bipyridine-functionalized organosilica nanotubes at 80℃; for 12h; Catalytic behavior; Kinetics; Reagent/catalyst; Inert atmosphere;	97%
With [Ir(OMe)(1,5-cyclooctadiene)]2 In benzene at 80℃; for 12h; Kinetics; Reagent/catalyst; Schlenk technique; Inert atmosphere;	94%

4-bromo-2-methoxypyridine (100367-39-3) + bis(pinacol)diborane (73183-34-3) → 2-methoxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine (408502-23-8)

Conditions	Yield
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate In N,N-dimethyl-formamide at 80℃;	100%
With C37H51ClFeNPPd; potassium acetate In 1,4-dioxane at 80℃; for 3h; Suzuki-Miyaura coupling; Inert atmosphere;	91%
With potassium acetate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride In N,N-dimethyl-formamide at 80℃;	74%

1,1-Diphenylethylene (530-48-3) + bis(pinacol)diborane (73183-34-3) → 2-(2,2-diphenylvinyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (83947-50-6)

Conditions	Yield
With (CH3Si(C6H4P(C6H3(CF3)2)2)2)Pd(SO3CF3); triethylaluminum In toluene at 20℃; for 24h; Inert atmosphere;	100%
With 2-Adamantanone In para-xylene at 130℃; under 760.051 Torr; for 20h; Inert atmosphere; regioselective reaction;	82%
trans-carbonyl(chloro)bis(triphenylphosphine)rhodium(I) In toluene; acetonitrile at 80℃; for 72h;

3-(trifluoromethyl)anisole (454-90-0) + bis(pinacol)diborane (73183-34-3) → 2-(3-methoxy-5-(trifluoromethyl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (479411-93-3)

Conditions	Yield
With [Ir(COD)(OMe)]2-Covalent organic framework (4-iPr) In n-heptane at 100℃; for 24h; Reagent/catalyst; Inert atmosphere;	100%
With pinacol borane; 4,4'-di-tert-butylbipyridine In cyclohexane at 80℃;	77%
With bis(1,5-cyclooctadiene)diiridium(I) dichloride; sodium methylate; 4,4'-di-tert-butyl-2,2'-bipyridine at 90℃; for 96h; Schlenk technique; Sealed tube; Inert atmosphere;	60%

4-bromo-1H-indole (52488-36-5) + bis(pinacol)diborane (73183-34-3) → indole-4-boronic acid pinacol ester (388116-27-6)

Conditions	Yield
With potassium acetate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 In dimethyl sulfoxide at 90℃; for 4h;	100%
With potassium acetate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 In dimethyl sulfoxide at 90℃; for 4h;	100%
With tris-(dibenzylideneacetone)dipalladium(0); potassium acetate; XPhos In 1,4-dioxane at 110℃; for 20h; Miyaura borylation; Inert atmosphere;	93%

thiophene (188290-36-0) + bis(pinacol)diborane (73183-34-3) → 2-thiopheneboronic acid pinacol ester (193978-23-3)

Conditions	Yield
With [Ir(COD)(OMe)]2-Covalent organic framework (4-iPr) at 100℃; for 24h; Inert atmosphere;	100%
In octane at 25℃; for 4h; Conversion of starting material;	88%
In octane at 25℃; for 4h; Conversion of starting material;	86%

5'-bromo-2'-fluorobiphenyl-2-carbonitrile (425378-71-8) + bis(pinacol)diborane (73183-34-3) → 2'-fluoro-5'-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)biphenyl-2-carbonitrile (425378-72-9)

Conditions	Yield
With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium acetate; dimethyl sulfoxide In 1,4-dioxane at 90℃; for 16h; Miyaura reaction;	100%
With potassium acetate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride In 1,4-dioxane; dimethyl sulfoxide at 90℃; for 16h;	100%
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate In 1,4-dioxane at 90℃; Miyaura reaction;	95%

bis(pinacol)diborane (73183-34-3) + 1-bromo-2-[2-[tris(1-methylethyl)silyl]ethynyl]benzene (261713-83-1) → tris(1-methylethyl){[2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]ethynyl}silane (573658-45-4)

Conditions	Yield
With potassium acetate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride In dimethyl sulfoxide at 90℃; for 18h;	100%
With potassium acetate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride In dimethyl sulfoxide (N2); for 18 h at 90°C; cooled to 20°C, Et2O added, washed with satd. aq. NaH2PO4 and satd. aq. NaCl, filtered (SiO2, hexane/EtOAc), evapd. (vac.), obtained as an oil;	99%

trifluoromethanesulfonic acid 2'-cyanobiphenyl-3-yl ester (342613-87-0) + bis(pinacol)diborane (73183-34-3) → 3'-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-biphenyl-2-carbonitrile (342613-89-2)

Conditions	Yield
With 1,1'-bis-(diphenylphosphino)ferrocene; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium acetate In 1,4-dioxane at 85℃; for 18h;	100%
With potassium acetate; 1,1'-bis-(diphenylphosphino)ferrocene; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 In 1,4-dioxane at 85℃; for 18h;	100%

(4-bromo-phenyl)-acetic acid methyl ester (41841-16-1) + bis(pinacol)diborane (73183-34-3) → methyl [4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]acetate (454185-98-9)

Conditions	Yield
With potassium acetate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride In 1,4-dioxane; dichloromethane at 90℃; for 4h;	100%
With potassium acetate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride In 1,4-dioxane; dichloromethane at 90℃; for 4h;	100%
With dichloro bis(acetonitrile) palladium(II); 1-(diphenylphosphino)ferrocene-1-(di-tert-butylphosphino)ferrocene; potassium acetate In 1,4-dioxane at 90℃; for 20h; Inert atmosphere;	83%

t-butyl 2-(4-bromophenyl)ethylcarbamate (120157-97-3) + bis(pinacol)diborane (73183-34-3) → tert-butyl N-[2-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]ethyl]carbamate (360792-43-4)

Conditions	Yield
With 1,1'-bis-(diphenylphosphino)ferrocene; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate In 1,4-dioxane at 80℃; for 18h;	100%
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate In 1,4-dioxane at 120℃; for 12h; Inert atmosphere;	85%
With potassium acetate In 1,4-dioxane at 80℃; Inert atmosphere;	80%

1,3-dibromobenzene (108-36-1) + bis(pinacol)diborane (73183-34-3) → 4,4,5,5-tetramethyl-2-[3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]-1,3,2-dioxaborolane (196212-27-8)

Conditions	Yield
With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium acetate In N,N-dimethyl-formamide at 90℃; for 48h; Inert atmosphere; Schlenk technique;	100%
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate In N,N-dimethyl-formamide at 80℃; for 16h; Inert atmosphere; Schlenk technique;	96%
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate In N,N-dimethyl-formamide at 80℃; for 24h; Suzuki-Miyaura Coupling;	93%

methyl 2-(3-bromophenyl)acetatee (150529-73-0) + bis(pinacol)diborane (73183-34-3) → methyl 2-[3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]acetate (478375-42-7)

Conditions	Yield
With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium acetate In 1,4-dioxane at 85℃; for 4h; Inert atmosphere;	100%
With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium acetate In 1,4-dioxane at 85℃; for 4h; Inert atmosphere;	100%
With potassium acetate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 In dimethyl sulfoxide at 80℃; for 3h; Suzuki reaction;	99%

C14H11BrN2 (950201-58-8) + bis(pinacol)diborane (73183-34-3) → C20H23BN2O2 (950201-59-9)

Conditions	Yield
With potassium acetate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 In dimethyl sulfoxide at 110 - 130℃;	100%

C11H13BrFNO (950201-68-0) + bis(pinacol)diborane (73183-34-3) → C17H25BFNO3 (950201-71-5)

Conditions	Yield
With potassium acetate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 In dimethyl sulfoxide at 120℃; for 16h;	100%

4-(4-bromophenoxy)-2-methylpyridine (950201-74-8) + bis(pinacol)diborane (73183-34-3) → 4-[4-(4,4,5,5-tetramethyl[1,3,2]dioxaborolan-2-yl)phenoxy]-2-methylpyridine (950201-75-9)

Conditions	Yield
With potassium acetate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 In 1,4-dioxane; N,N-dimethyl-formamide at 150℃; for 0.166667h; Microwave irradiation;	100%
With potassium acetate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 In dimethyl sulfoxide at 110℃; for 16h;	100%
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate	89%

bis(pinacol)diborane (73183-34-3) + 2-chloro-6-methoxypyrazine (33332-30-8) → 2-methoxy-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrazine (960503-91-7)

Conditions	Yield
With water; potassium acetate; tris-(dibenzylideneacetone)dipalladium(0); tricyclohexylphosphine In 1,2-dimethoxyethane at 150℃; for 3h;	100%
With potassium acetate; tris-(dibenzylideneacetone)dipalladium(0); tricyclohexylphosphine In 1,2-dimethoxyethane at 150℃; for 3h; Microwave irradiation;	100%
With tris-(dibenzylideneacetone)dipalladium(0); potassium acetate; tricyclohexylphosphine In 1,2-dimethoxyethane at 150℃; for 3h; Inert atmosphere; Microwave irradiation;	600 mg

4-bromo-2,6-difluorobenzonitrile (123843-67-4) + bis(pinacol)diborane (73183-34-3) → 2,6-difluoro-4-(4,4,5,5- tetramethyl-1,3,2-dioxaborolan-2-yl)benzonitrile (1003298-73-4)

Conditions	Yield
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate In 1,4-dioxane at 110℃; for 2h; Inert atmosphere;	100%
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate In 1,4-dioxane at 100℃; for 6h; Inert atmosphere;	55%
With tris-(dibenzylideneacetone)dipalladium(0); potassium acetate; XPhos In toluene at 110℃; for 16h; Inert atmosphere;	35%

5-heptyl-5'-[4-(trifluoromethylsulfonyl)phenyl]-2,2'-bipyridine (943301-79-9) + bis(pinacol)diborane (73183-34-3) → 5-heptyl-5'-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]-2,2'-bipyridine

Conditions	Yield
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate In 1,4-dioxane at 120℃;	100%
With 1,1'-bis-(diphenylphosphino)ferrocene; potassium acetate; PdCl2(1,1'-bis(diphenylphopsphino)ferrocene) In 1,4-dioxane at 120℃; for 18h;	90%

Upstream product

• 76-09-5 2,3-dimethyl-2,3-butane diol 
• 1630-79-1 tetrakis(dimethylamido)diborane 
• 25015-63-8 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane 
• 71-43-2 benzene 
• 203259-76-1 cis-[Pt(difluoroboryl)2(PPh₃)2] 
• 13675-18-8 tetrahydroxydiboron 
• 1301680-12-5 2-[(1E)-but-1-en-1-yl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 1109-15-5 tris(pentafluorophenyl)borate 
• 74-85-1 ethene 
• 158752-98-8 tetrakis(tetrahydropyrrole)boron 
• 110-83-8 cyclohexene 
• 13826-27-2 2,2'-bis(1,3,2-benzodioxaborole) 

Downstream Products

• 171364-79-7 2-(4-methoxyphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 171364-81-1 1-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)ethanone 
• 25015-63-8 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane 
• 255041-56-6 2-(2-tert-butoxyethyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 67562-21-4 4,4,5,5-tetramethyl-2-pentyl-1,3,2-dioxaborolane 
• 24388-23-6 2-phenyl-4,4,5,5-tetramethyl-1,3,2-dioxoborole 
• 141091-37-4 2-(cyclohex-1-en-1-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 157945-83-0 (E)-2-(3,3-dimethylbut-1-en-1-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 261638-97-5 2-(3,3-dimethylbut-1-en-2-yl)-4,4,5 ,5-tetramethyl-1,3 ,2-dioxaborolane 
• 286961-15-7 benzyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3,6-dihydro-1 (2H)-pyridinecarboxylate 
• 199999-46-7 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-4-phenyl-1-phenylpropan-1-one 
• 303030-12-8 4-amino-4'-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-biphenyl-3-carboxylic acid methyl ester 
• 303030-15-1 4-amino-4'''-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-[1,4';1',1'';4'',1''']quaterphenyl-3,2''-dicarboxylic acid dimethyl ester 

Relevant articles and documents

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