13675-18-8

Usage

InChI:InChI=1/B2H4O4/c3-1(4)2(5)6/h3-6H

Synthetic route

water (7732-18-5) + diboron tetrachloride (13701-67-2) → tetrahydroxydiboron (13675-18-8) + boric acid (11113-50-1)

Conditions	Yield
In water byproducts: HCl; hydrolysis of B2Cl4; dissolution of crude solid in degassed H2O, slow evapn. at room temp.;	A 70% B n/a

tetramethoxydiborane (7318-94-7) + water (7732-18-5) → methanol (67-56-1) + tetrahydroxydiboron (13675-18-8)

B2Br4(NH(CH3)2)2 (67183-19-1) + water (7732-18-5) → tetrahydroxydiboron (13675-18-8) + boric acid (11113-50-1)

Conditions	Yield
In tetrahydrofuran; water addn. of aq. THF to a soln. of boron compd. in THF, stirring for 2 d; dissolution in H2O, slow evapn. at room temp.;

tetrakis(dimethylamido)diborane (1630-79-1) + water (7732-18-5) → tetrahydroxydiboron (13675-18-8) + dimethyl amine (124-40-3)

water (7732-18-5) + diboron tetrachloride (13701-67-2) → hydrogenchloride (7647-01-0) + tetrahydroxydiboron (13675-18-8)

tetramethoxydiborane (7318-94-7) → tetrahydroxydiboron (13675-18-8) + boric acid (11113-50-1)

Conditions	Yield
With water In water at room temp. in vac.;
With hydrogenchloride In not given with dild. HCl at room temp. in vac.;
With H2O In water at room temp. in vac.;
With HCl In not given with dild. HCl at room temp. in vac.;

tetramethoxydiborane (7318-94-7) → tetrahydroxydiboron (13675-18-8)

Conditions	Yield
by hydrolysis;
by hydrolysis;

H4B2O2 → tetrahydroxydiboron (13675-18-8)

Conditions	Yield
With iodine
With I2

H2B2O2 → tetrahydroxydiboron (13675-18-8)

Conditions	Yield
In water evapn.;
With iodine In water
With I2 In water
In water evapn.;

dichlorobis(dimethylamino)diborane(4) (64541-76-0) → tetrahydroxydiboron (13675-18-8)

Conditions	Yield
With H2O

tetrakis(dimethylamido)diborane (1630-79-1) → tetrahydroxydiboron (13675-18-8) + N,N-dimethylammonium chloride (506-59-2)

Conditions	Yield
With hydrogenchloride; water
With H2O; HCl

tetrakis(dimethylamido)diborane (1630-79-1) → tetrahydroxydiboron (13675-18-8) + dimethyl amine (124-40-3)

Conditions	Yield
With H2O distn. in high vac.;

diboron tetrachloride (13701-67-2) → tetrahydroxydiboron (13675-18-8)

Conditions	Yield
With iodine In water oxydation by I2 in acidic soln.;
With I2; acid In water oxydation by I2 in acidic soln.;

tris(dimethylamino)monochlorodiborane(4) (7360-75-0) → tetrahydroxydiboron (13675-18-8)

Conditions	Yield
With H2O in acidic soln.;

water (7732-18-5) + tetrakis(tetrahydropyrrole)boron (158752-98-8) → tetrahydroxydiboron (13675-18-8)

Conditions	Yield
at 100℃; Inert atmosphere;	8.5 g

dihydroxy-methyl-borane (13061-96-6) + bis(pinacol)diborane (73183-34-3) → tetrahydroxydiboron (13675-18-8)

Conditions	Yield
With trifluoroacetic acid In dichloromethane at 20℃;

2,2'-bis(1,3,2-benzodioxaborole) (13826-27-2) → tetrahydroxydiboron (13675-18-8) + benzene-1,2-diol (120-80-9)

Conditions	Yield
With water In N,N-dimethyl acetamide at 80℃; for 8h; Inert atmosphere; Sealed tube;

tetrahydroxydiboron (13675-18-8) + 3-[2-bromo-5-(hydroxymethyl)phenyl]propan-1-ol → (1-hydroxy-4,5-dihydro-3H-2,1-benzoxaborepin-7-yl)methanol

Conditions	Yield
With chloro(2-dicyclohexylphosphino-2’,4’,6’-triisopropyl-1,1‘-biphenyl)[2-(2’-amino-1,1‘-biphenyl’)]palladium(II); potassium acetate; XPhos In ethanol at 80℃; for 1h; Inert atmosphere;	100%

potassium hydrogenfluoride (1279123-63-5) + tetrahydroxydiboron (13675-18-8) + 1-chloro-3,5-dimethoxybenzene (7051-16-3) → potassium (3,4-dimethoxyphenyl)trifluoroborate

Conditions	Yield
With PdCl(C6H4C6H4NH2)(Cy2PC6H4-2-C6H2-2',4',6'-i-Pr3); Cy2PC6H4-2-C6H2-2',4',6'-i-Pr3; K acetate In ethanol aryl chloride reacted with B2(OH)4 in EtOH in presence of catalyst (Pt-complex - ligand) and K acetate at 80°C for 2 h; subjected to aq. workup; treated with KHF2; purified by Soxlet extn.;	99%
With NaOC(CH3)3; 2,4,6-(i-Pr)3C6H2C6H4[2-P(cyclo-C6H11)2]; KOAc In methanol; ethanol mixt. org. compound, B2(OH)4, Pd-complex, 2,4,6-(i-Pr)3C6H2C6H4-2-P(c-C6H11)2, KOAc in EtOH at 80°C for 18 h, cooled to room temp., filtered, concd. aq. KHF2 was added dropwise in MeOH at 0°C, mixt. wasstirred at room temp. for 30 min;	92%

potassium hydrogenfluoride (1279123-63-5) + tetrahydroxydiboron (13675-18-8) + 4-methoxyphenyl triflate (66107-29-7) → potassium 4-(methoxy)phenyltrifluoroborate

Conditions	Yield
With PdCl(C6H4C6H4NH2)(Cy2PC6H4-2-C6H2-2',4',6'-i-Pr3); Cy2PC6H4-2-C6H2-2',4',6'-i-Pr3; K acetate In ethanol aryl triflate reacted with B2(OH)4 in EtOH in presence of catalyst (Pt-complex - ligand) and K acetate at 80°C for 2 h; subjected to aq. workup; treated with KHF2; purified by Soxlet extn.;	99%

tetrahydroxydiboron (13675-18-8) + (R)-1,1-bis(3,5-dimethylphenyl)-2-phenylethane-1,2-diol → (5R,5'R)-4,4,4',4'-tetrakis(3,5-dimethylphenyl)-5,5'-diphenyl-2,2'-bi(1,3,2-dioxaborolane)

Conditions	Yield
In tetrahydrofuran at 70℃; for 3h; Molecular sieve;	99%

tetrahydroxydiboron (13675-18-8) + (R)-2-phenyl-1,1-di-o-tolylethane-1,2-diol → (5R,5'R)-5,5'-diphenyl-4,4,4',4'-tetra-o-tolyl-2,2'-bi(1,3,2-dioxaborolane)

Conditions	Yield
In tetrahydrofuran at 70℃; for 3h; Molecular sieve;	99%
In tetrahydrofuran at 70℃; for 4h; Molecular sieve; Schlenk technique; Inert atmosphere;	95%

tetrahydroxydiboron (13675-18-8) + (R)-1,1-bis(2,5-dimethylphenyl)-2-phenylethane-1,2-diol → (5R,5'R)-4,4,4',4'-tetrakis(2,5-dimethylphenyl)-5,5'-diphenyl-2,2'-bi(1,3,2-dioxaborolane)

Conditions	Yield
In tetrahydrofuran at 70℃; for 3h; Molecular sieve;	99%
In tetrahydrofuran at 70℃; for 4h; Molecular sieve; Schlenk technique; Inert atmosphere;	94%

tetrahydroxydiboron (13675-18-8) + 2-methoxy-4-(2H-1,2,3-triazol-2-yl)benzenediazonium trifluoromethanesulfonic salt → (2-methoxy-4-(2H-1,2,3-triazol-2-yl)phenyl)boronic acid

Conditions	Yield
In water at 25℃; for 3h;	99%

potassium hydrogenfluoride (1279123-63-5) + tetrahydroxydiboron (13675-18-8) + 2-methyl-3-buten-2-ol (115-18-4) → potassium trifluoro(3-methylbut-2-en-1-yl)borate

Conditions	Yield
[1,3-bis(phenylselenomethyl)phenyl]palladium(II) chloride In methanol; dimethyl sulfoxide react. (B(OH)2)2 with olefine at 50°C for 16 h in mixt. DMSO-MeOH, aq. KHF2 was added;	98%

potassium hydrogenfluoride (1279123-63-5) + tetrahydroxydiboron (13675-18-8) + (C6H5O2S)(CO2CH3)C3H3CHCH2 → (C6H5O2S)(CO2CH3)C5H7BF3(1-)*K(1+)=(C6H5O2S)(COOCH3)C5H7BF3K

Conditions	Yield
[1,3-bis(phenylselenomethyl)phenyl]palladium(II) chloride In water; dimethyl sulfoxide B complex treated with ligand in DMSO at 40°C in the presence ofPd catalyst (5 mol%), reacted for 5 h, treated with aq. KHF2;	98%

potassium hydrogenfluoride (1279123-63-5) + tetrahydroxydiboron (13675-18-8) + 1-Chloro-4-fluorobenzene (352-33-0) → potassim 4-fluorophenyltrifluoroborate

Conditions	Yield
With PdCl(C6H4C6H4NH2)(Cy2PC6H4-2-C6H2-2',4',6'-i-Pr3); Cy2PC6H4-2-C6H2-2',4',6'-i-Pr3; K acetate In ethanol aryl chloride reacted with B2(OH)4 in EtOH in presence of catalyst (Pt-complex - ligand) and K acetate at 80°C for 2.5 h; subjected to aq. workup; treated with KHF2; purified by Soxlet extn.;	98%
With NaOC(CH3)3; 2,4,6-(i-Pr)3C6H2C6H4[2-P(cyclo-C6H11)2]; KOAc In methanol; ethanol mixt. org. compound, B2(OH)4, Pd-complex, 2,4,6-(i-Pr)3C6H2C6H4-2-P(c-C6H11)2, KOAc in EtOH at 80°C for 18 h, cooled to room temp., filtered, concd. aq. KHF2 was added dropwise in MeOH at 0°C, mixt. wasstirred at room temp. for 30 min;	80%

potassium hydrogenfluoride (1279123-63-5) + tetrahydroxydiboron (13675-18-8) + 4-bromo-phenol (106-41-2) → potassium (4-hydroxyphenyl)trifluoroborate

Conditions	Yield
With PdCl(C6H4C6H4NH2)(Cy2PC6H4-2-C6H2-2',4',6'-i-Pr3); Cy2PC6H4-2-C6H2-2',4',6'-i-Pr3; K acetate In ethanol aryl bromide reacted with B2(OH)4 in EtOH in presence of catalyst (Pt-complex - ligand) and K acetate at 80°C for 1 h; subjected to aq. workup; treated with KHF2; purified by Soxlet extn.;	98%

potassium hydrogenfluoride (1279123-63-5) + tetrahydroxydiboron (13675-18-8) + 1-bromo-3,5-dimethoxybenzene (20469-65-2) → potassium (3,4-dimethoxyphenyl)trifluoroborate

Conditions	Yield
With PdCl(C6H4C6H4NH2)(Cy2PC6H4-2-C6H2-2',4',6'-i-Pr3); Cy2PC6H4-2-C6H2-2',4',6'-i-Pr3; K acetate In ethanol aryl bromide reacted with B2(OH)4 in EtOH in presence of catalyst (Pt-complex - ligand) and K acetate at 80°C for 4 h; subjected to aq. workup; treated with KHF2; purified by Soxlet extn.;	98%

potassium hydrogenfluoride (1279123-63-5) + tetrahydroxydiboron (13675-18-8) + 3-monochlorophenol (108-43-0) → potassium (3-hydroxyphenyl)trifluoroborate (871231-45-7)

Conditions	Yield
With PdCl(C6H4C6H4NH2)(Cy2PC6H4-2-C6H2-2',4',6'-i-Pr3); Cy2PC6H4-2-C6H2-2',4',6'-i-Pr3; K acetate In ethanol aryl chloride reacted with B2(OH)4 in EtOH in presence of catalyst (Pt-complex - ligand) and K acetate at 80°C for 2 h; subjected to aq. workup; treated with KHF2; purified by Soxlet extn.;	98%

5-bromobenzofuran (23145-07-5) + tetrahydroxydiboron (13675-18-8) → 2,3-dihydro-1-benzofuran-5-ylboronic acid (331834-13-0)

Conditions	Yield
In methanol at 15℃; for 3h; Microwave irradiation;	98%
With potassium tert-butylate In methanol at 0 - 20℃;

5-bromobenzo[b]thiophene (4923-87-9) + tetrahydroxydiboron (13675-18-8) → benzo[b]thiophen-5-ylboronic acid (845872-49-3)

Conditions	Yield
In methanol at 15℃; for 3h; Microwave irradiation;	98%
With potassium tert-butylate In methanol at 0 - 20℃;

tetrahydroxydiboron (13675-18-8) + phenyltrimethylammonium iodide (98-04-4) → phenylboronic acid (98-80-6)

Conditions	Yield
In methanol at 15℃; for 3h; Microwave irradiation;	98%

tetrahydroxydiboron (13675-18-8) + trimethyl-p-tolylammonium iodide (6140-15-4) → 4-methylphenylboronic acid (5720-05-8)

Conditions	Yield
In methanol at 15℃; for 3h; Microwave irradiation;	98%

tetrahydroxydiboron (13675-18-8) + 4-nitrobenzenediazonium trifluoromethanesulfonate → 4-nitrophenylboronic acid (24067-17-2)

Conditions	Yield
In water at 20℃; for 3.5h;	98%

potassium hydrogenfluoride (1279123-63-5) + tetrahydroxydiboron (13675-18-8) + 1,1-diacetoxy-2-propene (869-29-4) → potassium trifluoro(3-acetoxy-2-propenyl)borate

Conditions	Yield
[1,3-bis(phenylselenomethyl)phenyl]palladium(II) chloride In water; dimethyl sulfoxide B complex treated with ligand in DMSO at 40°C in the presence ofPd catalyst (5 mol%), reacted for 36 h, treated with aq. KHF2;	97%

potassium hydrogenfluoride (1279123-63-5) + tetrahydroxydiboron (13675-18-8) + methyl 3-chlorobenzoate (2905-65-9) → potassium (meta-methoxycarbonylphenyl)trifluoroborate (1242733-94-3)

Conditions	Yield
With PdCl(C6H4C6H4NH2)(Cy2PC6H4-2-C6H2-2',4',6'-i-Pr3); Cy2PC6H4-2-C6H2-2',4',6'-i-Pr3; K acetate In ethanol aryl chloride reacted with B2(OH)4 in EtOH in presence of catalyst (Pt-complex - ligand) and K acetate at 80°C for 2.5 h; subjected to aq. workup; treated with KHF2; purified by Soxlet extn.;	97%

tetrahydroxydiboron (13675-18-8) + 4-fluoro-1-iodobenzene (352-34-1) → 4-fluoroboronic acid (1765-93-1)

Conditions	Yield
In methanol at 15℃; for 1h; Microwave irradiation;	97%
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate In dimethyl sulfoxide at 60℃; for 0.333333h; Temperature; Solvent; Reagent/catalyst;	74%
In methanol; water at -5℃; for 0.166667h; UV-irradiation; Flow reactor; chemoselective reaction;	100 %Spectr.

tetrahydroxydiboron (13675-18-8) + 1-bromo-4-(trifluoromethoxy)benzene (407-14-7) → 4-trifluoromethoxyphenylboronic acid (139301-27-2)

Conditions	Yield
In methanol at 15℃; for 3h; Microwave irradiation;	97%
With potassium tert-butylate In methanol at 0 - 20℃;

tetrahydroxydiboron (13675-18-8) + ethylene glycol (107-21-1) → (2,2’-bi(1,3,2-dioxaborolane)) (13826-24-9)

Conditions	Yield
With magnesium sulfate In tetrahydrofuran at 20℃; for 24h; Sealed tube;	97%
With magnesium sulfate In tetrahydrofuran at 20℃; for 48h; Inert atmosphere;	74%

potassium hydrogenfluoride (1279123-63-5) + tetrahydroxydiboron (13675-18-8) + 4-chloromethoxybenzene (623-12-1) → potassium 4-(methoxy)phenyltrifluoroborate

Conditions	Yield
With Pd(O2CCH3)2; Cy2PC6H4-2-C6H2-2',4',6'-i-Pr3; K acetate In ethanol Pd acetate, ligand and K acetate stirred in EtOH at 80°C for 20 min; B2(OH)4 in EtOH and aryl chloride added; reacted at 80°C for 1 h; subjected to aq. workup; treated with KHF2;	95%
With PdCl(C6H4C6H4NH2)(Cy2PC6H4-2-C6H2-2',4',6'-i-Pr3); Cy2PC6H4-2-C6H2-2',4',6'-i-Pr3; K acetate In ethanol aryl chloride reacted with B2(OH)4 in EtOH in presence of catalyst (Pt-complex - ligand) and K acetate at 80°C for 2 h; subjected to aq. workup; treated with KHF2; purified by Soxlet extn.;	93%
With NaOC(CH3)3; 2,4,6-(i-Pr)3C6H2C6H4[2-P(cyclo-C6H11)2]; KOAc In methanol; ethanol mixt. org. compound, B2(OH)4, Pd-complex, 2,4,6-(i-Pr)3C6H2C6H4-2-P(c-C6H11)2, KOAc in EtOH at 80°C for 18 h, cooled to room temp., filtered, concd. aq. KHF2 was added dropwise in MeOH at 0°C, mixt. was stirred at room temp. for 30 min;	90%

potassium hydrogenfluoride (1279123-63-5) + tetrahydroxydiboron (13675-18-8) + 2-methylchlorobenzene (95-49-8) → potassium o-tolyltrifluoroborate

Conditions	Yield
With PdCl(C6H4C6H4NH2)(Cy2PC6H4-2-C6H2-2',4',6'-i-Pr3); Cy2PC6H4-2-C6H2-2',4',6'-i-Pr3; K acetate In ethanol aryl chloride reacted with B2(OH)4 in EtOH in presence of catalyst (Pt-complex - ligand) and K acetate at 80°C for 3.5 h; subjected to aq. workup; treated with KHF2; purified by Soxlet extn.;	95%
With NaOC(CH3)3; 2,4,6-(i-Pr)3C6H2C6H4[2-P(cyclo-C6H11)2]; KOAc In methanol; ethanol mixt. org. compound, B2(OH)4, Pd-complex, 2,4,6-(i-Pr)3C6H2C6H4-2-P(c-C6H11)2, KOAc in EtOH at 80°C for 18 h, cooled to room temp., filtered, concd. aq. KHF2 was added dropwise in MeOH at 0°C, mixt. wasstirred at room temp. for 30 min;	75%

potassium hydrogenfluoride (1279123-63-5) + tetrahydroxydiboron (13675-18-8) + para-bromoacetophenone (99-90-1) → potassium 4-acetylphenyltrifluoroborate

Conditions	Yield
With PdCl(C6H4C6H4NH2)(Cy2PC6H4-2-C6H2-2',4',6'-i-Pr3); Cy2PC6H4-2-C6H2-2',4',6'-i-Pr3; K acetate In ethanol aryl bromide reacted with B2(OH)4 in EtOH in presence of catalyst (Pt-complex - ligand) and K acetate at 80°C for 2 h; subjected to aq. workup; treated with KHF2; purified by Soxlet extn.;	95%

potassium hydrogenfluoride (1279123-63-5) + tetrahydroxydiboron (13675-18-8) + 1-Bromo-4-fluorobenzene (460-00-4) → potassim 4-fluorophenyltrifluoroborate

Conditions	Yield
With PdCl(C6H4C6H4NH2)(Cy2PC6H4-2-C6H2-2',4',6'-i-Pr3); Cy2PC6H4-2-C6H2-2',4',6'-i-Pr3; K acetate In ethanol aryl bromide reacted with B2(OH)4 in EtOH in presence of catalyst (Pt-complex - ligand) and K acetate at 80°C for 4 h; subjected to aq. workup; treated with KHF2; purified by Soxlet extn.;	95%

tetrahydroxydiboron (13675-18-8) + (3aR,9bR)-tert-butyl 9b-((4- fluorophenyl)sulfonyl)-7-iodo-3a,4,5 ,9b-tetrahydro- 1H-benzo [e]indole-3 -carboxylate → ((3aR,9bR)-3-(tert-butoxycarbonyl)-9b-((4-fluorophenyl)sulfonyl)-2,3,3a,4,5,9b-hexahydro-1H-benzo[e]indol-7-yl)boronic acid

Conditions	Yield
With chloro(2-dicyclohexylphosphino-2’,4’,6’-triisopropyl-1,1‘-biphenyl)[2-(2’-amino-1,1‘-biphenyl’)]palladium(II); potassium acetate; XPhos In ethanol at 55℃; for 2.4h; Time; Inert atmosphere;	95%
With chloro(2-dicyclohexylphosphino-2’,4’,6’-triisopropyl-1,1‘-biphenyl)[2-(2’-amino-1,1‘-biphenyl’)]palladium(II); potassium acetate; XPhos In ethanol at 55℃; for 18h;	80%

potassium hydrogenfluoride (1279123-63-5) + tetrahydroxydiboron (13675-18-8) + (E)-2-Hexen-1-ol (928-95-0) → (E)-trifluoro-(hex-2-en-1-yl)-λ4-borane potassium

Conditions	Yield
[1,3-bis(phenylselenomethyl)phenyl]palladium(II) chloride In methanol; dimethyl sulfoxide react. (B(OH)2)2 with olefine at 50°C for 16 h in mixt. DMSO-MeOH, aq. KHF2 was added;	94%

potassium hydrogenfluoride (1279123-63-5) + tetrahydroxydiboron (13675-18-8) + 3-bromo-N,N-dimethylaniline (16518-62-0) → potassium (3-(dimethylamino)phenyl)trifluoroborate (1386231-64-6)

Conditions	Yield
With PdCl(C6H4C6H4NH2)(Cy2PC6H4-2-C6H2-2',4',6'-i-Pr3); Cy2PC6H4-2-C6H2-2',4',6'-i-Pr3; K acetate In ethanol aryl bromide reacted with B2(OH)4 in EtOH in presence of catalyst (Pt-complex - ligand) and K acetate at 80°C for 3.5 h; subjected to aq.workup; treated with KHF2; purified by Soxlet extn.;	94%

Upstream product

• 7318-94-7 tetramethoxydiborane 
• 7732-18-5 water 
• 67183-19-1 B₂Br₄(NH(CH₃)2)2 
• 1630-79-1 tetrakis(dimethylamido)diborane 
• 13701-67-2 diboron tetrachloride 
• 64541-76-0 dichlorobis(dimethylamino)diborane⁽⁴⁾ 
• 7360-75-0 tris(dimethylamino)monochlorodiborane⁽⁴⁾ 
• 158752-98-8 tetrakis(tetrahydropyrrole)boron 
• 13061-96-6 dihydroxy-methyl-borane 
• 73183-34-3 bis(pinacol)diborane 
• 13826-27-2 2,2'-bis(1,3,2-benzodioxaborole) 

Downstream Products

• 11113-50-1 boric acid 
• 1333-74-0 hydrogen 
• 13709-94-9 potassium metaborate 
• 1258238-88-8 potassium (4-benzoylphenyl)trifluoroborate 

Relevant academic research and scientific papers

Metal-Free Direct Deoxygenative Borylation of Aldehydes and Ketones

Direct conversion of aldehydes and ketones into alkylboronic esters via deoxygenative borylation represents an unknown yet highly desirable transformation. Herein, we present a one-step and metal-free method for carbonyl deoxy-borylation under mild conditions. A wide range of aromatic aldehydes and ketones are tolerated and successfully converted into the corresponding benzylboronates. By the same deoxygenation manifold with aliphatic aldehydes and ketones, we also enable a concise synthesis of 1,1,2-tris(boronates), a family of compounds that currently lack efficient synthetic methods. Given its simplicity and versatility, we expect that this novel borylation approach could show great promise in organoboron synthesis and inspire more carbonyl deoxygenative transformations in both academic and industrial settings.

Virtues of Volatility: A Facile Transesterification Approach to Boronic Acids

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Method for synthesizing aryl three fluoro potassium borate method

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The solid-state structure of diboronic acid, B2(OH)4

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