374790-93-9|2-(2-Furanyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane| Ambeed

Structure of 374790-93-9

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Quality Control of [ 374790-93-9 ] Purity: 98% SDS Specification

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Product Details of [ 374790-93-9 ]

CAS No. :	374790-93-9
Formula :	C₁₀H₁₅BO₃
M.W :	194.04
SMILES Code :	CC1(C)C(C)(C)OB(C2=CC=CO2)O1
MDL No. :	MFCD02094008
InChI Key :	GWEWQKZABZXLJH-UHFFFAOYSA-N
Pubchem ID :	11356013

Safety of [ 374790-93-9 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302
Precautionary Statements:	P280-P305+P351+P338

Computational Chemistry of [ 374790-93-9 ] Show Less

Physicochemical Properties

Num. heavy atoms	14
Num. arom. heavy atoms	5
Fraction Csp3	0.6
Num. rotatable bonds	1
Num. H-bond acceptors	3.0
Num. H-bond donors	0.0
Molar Refractivity	55.18
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	31.6 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	0.0
Log P_o/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry	2.01
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	1.58
Log P_o/w (MLOGP)? MLOGP: Topological method implemented from Moriguchi I. et al. 1992 Chem. Pharm. Bull. Moriguchi I. et al. 1994 Chem. Pharm. Bull. Lipinski PA. et al. 2001 Adv. Drug. Deliv. Rev.	0.34
Log P_o/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com	1.25
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	1.04

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-2.51
Solubility	0.603 mg/ml ; 0.00311 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Soluble
Log S (Ali)? Ali: Topological method implemented from Ali J. et al. 2012 J. Chem. Inf. Model.	-2.3
Solubility	0.971 mg/ml ; 0.00501 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Soluble
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com	-3.21
Solubility	0.119 mg/ml ; 0.000612 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Soluble

Pharmacokinetics

GI absorption? Gatrointestinal absorption: according to the white of the BOILED-Egg	High
BBB permeant? BBB permeation: according to the yolk of the BOILED-Egg	Yes
P-gp substrate? P-glycoprotein substrate: SVM model built on 1033 molecules (training set) and tested on 415 molecules (test set) 10-fold CV: ACC=0.72 / AUC=0.77 External: ACC=0.88 / AUC=0.94	Yes
CYP1A2 inhibitor? Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set) and tested on 3000 molecules (test set) 10-fold CV: ACC=0.83 / AUC=0.90 External: ACC=0.84 / AUC=0.91	No
CYP2C19 inhibitor? Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set) and tested on 3000 molecules (test set) 10-fold CV: ACC=0.80 / AUC=0.86 External: ACC=0.80 / AUC=0.87	No
CYP2C9 inhibitor? Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set) and tested on 2075 molecules (test set) 10-fold CV: ACC=0.78 / AUC=0.85 External: ACC=0.71 / AUC=0.81	No
CYP2D6 inhibitor? Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set) and tested on 1068 molecules (test set) 10-fold CV: ACC=0.79 / AUC=0.85 External: ACC=0.81 / AUC=0.87	No
CYP3A4 inhibitor? Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set) and tested on 2579 molecules (test set) 10-fold CV: ACC=0.77 / AUC=0.85 External: ACC=0.78 / AUC=0.86	Yes
Log Kp (skin permeation)? Skin permeation: QSPR model implemented from Potts RO and Guy RH. 1992 Pharm. Res.	-6.06 cm/s

Druglikeness

Lipinski? Lipinski (Pfizer) filter: implemented from Lipinski CA. et al. 2001 Adv. Drug Deliv. Rev. MW ≤ 500 MLOGP ≤ 4.15 N or O ≤ 10 NH or OH ≤ 5	0.0
Ghose? Ghose filter: implemented from Ghose AK. et al. 1999 J. Comb. Chem. 160 ≤ MW ≤ 480 -0.4 ≤ WLOGP ≤ 5.6 40 ≤ MR ≤ 130 20 ≤ atoms ≤ 70	None
Veber? Veber (GSK) filter: implemented from Veber DF. et al. 2002 J. Med. Chem. Rotatable bonds ≤ 10 TPSA ≤ 140	0.0
Egan? Egan (Pharmacia) filter: implemented from Egan WJ. et al. 2000 J. Med. Chem. WLOGP ≤ 5.88 TPSA ≤ 131.6	0.0
Muegge? Muegge (Bayer) filter: implemented from Muegge I. et al. 2001 J. Med. Chem. 200 ≤ MW ≤ 600 -2 ≤ XLOGP ≤ 5 TPSA ≤ 150 Num. rings ≤ 7 Num. carbon > 4 Num. heteroatoms > 1 Num. rotatable bonds ≤ 15 H-bond acc. ≤ 10 H-bond don. ≤ 5	1.0
Bioavailability Score? Abbott Bioavailability Score: Probability of F > 10% in rat implemented from Martin YC. 2005 J. Med. Chem.	0.55

Medicinal Chemistry

PAINS? Pan Assay Interference Structures: implemented from Baell JB. & Holloway GA. 2010 J. Med. Chem.	0.0 alert
Brenk? Structural Alert: implemented from Brenk R. et al. 2008 ChemMedChem	1.0 alert: heavy_metal
Leadlikeness? Leadlikeness: implemented from Teague SJ. 1999 Angew. Chem. Int. Ed. 250 ≤ MW ≤ 350 XLOGP ≤ 3.5 Num. rotatable bonds ≤ 7	No; 1 violation:MW<1.0
Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) based on 1024 fragmental contributions (FP2) modulated by size and complexity penaties, trained on 12'782'590 molecules and tested on 40 external molecules (r² = 0.94)	3.35

Application In Synthesis of [ 374790-93-9 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Upstream synthesis route of [ 374790-93-9 ]
Downstream synthetic route of [ 374790-93-9 ]

[ 374790-93-9 ] Synthesis Path-Upstream 1~11

1
[ 584-12-3 ]
[ 61676-62-8 ]
[ 374790-93-9 ]

Yield	Reaction Conditions	Operation in experiment
78%	Stage #1: With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 2 h; Stage #2: at -78 - 20℃; Stage #3: With methanol In tetrahydrofuran; hexane	General procedure: n-BuLi in hexane (1.6 M, 65 mL, 0.10 mol) was slowly added toa solution of 2-bromothiophene (11 g, 0.068 mol) in THF (200 mL) at 78 C. After stirring for 2 h at this temperature, the mixturewas added to a solution of 2-isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (13 g, 0.068 mol) in 150 mL of THF. The mixture was warmed to room temperature and stirred overnight. The reactionwas terminated by adding a small amount of methanol and the resultant solution was washed with water three times. The solution was dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The crude product was purified by silica gel column chromatography (eluent: hexane) to give 2-(4,4,5,5-tetramethyl-1,3,2-dioxaborane-2-yl)thiophene

References: [1] Polymer, 2012, vol. 53, # 20, p. 4380 - 4387.

2
[ 110-00-9 ]
[ 25015-63-8 ]
[ 374790-93-9 ]

Yield	Reaction Conditions	Operation in experiment
76%	With (^CyAPDI)CoCH₃ In neat (no solvent) at 23℃; for 10 h;	EXAMPLE 9 - Borylation of Aromatic Five-Membered Heterocycle According to the reaction scheme illustrated in Figure 2(a), a scintillation vial (with a magnetic stir bar) was charged with cobalt complex (0.01 mmol) selected from 1-4, 2 methylfuran (1 mmol) and pinacolborane (1 mmol). The reaction was monitored by the analysis of an aliquot of the mixture by GC-FID. The mixture was allowed to stir to completion at room temperature and was quenched by exposure to air. The resulting solid was solubilized in CDC1₃, 1 ] 3 passed through a plug of silica gel in a Pasteur pipette and then analyzed by H and C NMR spectroscopy without further purification. If desired, the foregoing reaction can also be administered in 2 ml of tetrahydrofuran (THF). Figure 2(a) provides conversion percentages for cobalt complexes 1-4 with values in parenthesis as isolated yields. Further, Figure 2(b) details additional borylation products achieved with Co complexes 2 and 3 according to the foregoing reaction parameters.

References: [1] Patent: WO2015/89119, 2015, A1, . Location in patent: Page/Page column 34.
[2] Chemistry - An Asian Journal, 2010, vol. 5, # 7, p. 1657 - 1666.

3
[ 110-00-9 ]
[ 73183-34-3 ]
[ 374790-93-9 ]

Yield	Reaction Conditions	Operation in experiment
45%	With (1,5-cyclooctadiene)(methoxy)iridium(I) dimer; 4,4'-di-tert-butyl-2,2'-bipyridine In hexane at 20℃; for 16 h;	Example 2 illustrates the sp²-carbon borylation and hydrogenation of a furan substrate to form a corresponding 2-substituted sp³-carbon borylated tetrahydrofuran. Scheme 12 illustrates sp²-carbon borylation of furan with an iridium-based catalyst ([IrOMe(cod)]₂and dtbpy) in hexane (rt for 16 h). The sp²-carbon borylated product is hydrogenated using hydrogen with a rhodium-based catalyst (Rh/Al₂O₃) in ethanol (rt for 15 h) to form the corresponding hydrogenated, 2-substituted sp³-carbon borylated tetrahydrofuran product.

References: [1] Patent: US2018/51042, 2018, A1, . Location in patent: Paragraph 0056.
[2] Journal of the American Chemical Society, 2005, vol. 127, # 41, p. 14263 - 14278.

4
[ 54829-48-0 ]
[ 25015-63-8 ]
[ 374790-93-9 ]

References: [1] Journal of Organometallic Chemistry, 2001, vol. 640, # 1-2, p. 197 - 199.
[2] Journal of Organometallic Chemistry, 2001, vol. 640, # 1-2, p. 197 - 199.

5
[ 110-00-9 ]
[ 25015-63-8 ]
[ 374790-93-9 ]

References: [1] Science, 2015, vol. 349, # 6247, p. 513 - 516.
[2] Chemistry - An Asian Journal, 2010, vol. 5, # 7, p. 1657 - 1666.

6
[ 110-00-9 ]
[ 61676-62-8 ]
[ 374790-93-9 ]

References: [1] Chemistry - A European Journal, 2009, vol. 15, # 47, p. 12978 - 12992.

7
[ 110-00-9 ]
[ 374790-93-9 ]

References: [1] Organic Process Research and Development, 2018, vol. 22, # 11, p. 1489 - 1499.

8
[ 110-00-9 ]
[ 73183-34-3 ]
[ 374790-93-9 ]

References: [1] Journal of the American Chemical Society, 2005, vol. 127, # 41, p. 14263 - 14278.

9
[ 110-00-9 ]
[ 73183-34-3 ]
[ 374790-93-9 ]
[ 248924-59-6 ]

References: [1] Tetrahedron Letters, 2002, vol. 43, # 32, p. 5649 - 5651.

10
[ 76-09-5 ]
[ 374790-93-9 ]

References: [1] Journal of the American Chemical Society, 2016, vol. 138, # 30, p. 9521 - 9532.

11
[ 1613405-38-1 ]
[ 75593-28-1 ]
[ 33501-91-6 ]
[ 374790-93-9 ]

References: [1] Journal of the American Chemical Society, 2016, vol. 138, # 30, p. 9521 - 9532.

[ 374790-93-9 ] Synthesis Path-Downstream 1~35

1
[ 54829-48-0 ]
[ 25015-63-8 ]
[ 374790-93-9 ]

References: [1]Journal of Organometallic Chemistry,2001,vol. 640,p. 197 - 199.
[2]Journal of Organometallic Chemistry,2001,vol. 640,p. 197 - 199.

2
[ 28735-21-9 ]
[ 374790-93-9 ]
3-(2-furyl)-1,2,4-triazine [ No CAS ]

References: [1]Synlett,2002,p. 447 - 450.

3
[ 110-00-9 ]
[ 73183-34-3 ]
[ 374790-93-9 ]
[ 248924-59-6 ]
2,5-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)furan [ No CAS ]

References: [1]Tetrahedron Letters,2002,vol. 43,p. 5649 - 5651.

4
[ 110-00-9 ]
[ 73183-34-3 ]
[ 374790-93-9 ]

Yield	Reaction Conditions	Operation in experiment
45%	With (1,5-cyclooctadiene)(methoxy)iridium(I) dimer; 4,4'-di-tert-butyl-2,2'-bipyridine; In hexane; at 20℃; for 16h;	Example 2 illustrates the sp2-carbon borylation and hydrogenation of a furan substrate to form a corresponding 2-substituted sp3-carbon borylated tetrahydrofuran. Scheme 12 illustrates sp2-carbon borylation of furan with an iridium-based catalyst ([IrOMe(cod)]2 and dtbpy) in hexane (rt for 16 h). The sp2-carbon borylated product is hydrogenated using hydrogen with a rhodium-based catalyst (Rh/Al2O3) in ethanol (rt for 15 h) to form the corresponding hydrogenated, 2-substituted sp3-carbon borylated tetrahydrofuran product.

References: [1]Patent: US2018/51042,2018,A1 .Location in patent: Paragraph 0056.
[2]Journal of the American Chemical Society,2005,vol. 127,p. 14263 - 14278.

5
[ 72601-11-7 ]
[ 374790-93-9 ]
2,2-dimethyl-3,3'-bifuran-5(2H)-one [ No CAS ]

References: [1]Journal of Organic Chemistry,2007,vol. 72,p. 9510 - 9517.

7
[ 110-00-9 ]
[ 73183-34-3 ]
[ 374790-93-9 ]
2,5-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)furan [ No CAS ]

References: [1]Journal of the American Chemical Society,2005,vol. 127,p. 14263 - 14278.

8
[ 13331-23-2 ]
N-[5-bromo-6-[4-(phenylmethoxy)phenyl]-1-[[2-(trimethylsilyl)ethoxy]methyl]-1H-indazol-3-yl]butanamide [ No CAS ]
[ 374790-93-9 ]
[ 1438429-57-2 ]

Yield	Reaction Conditions	Operation in experiment
		353 mg of 2-furylboronic acid, 624 mg of sodium carbonate in 25 cm3 of water, and 311 mg of tetrakis(triphenylphosphine)palladium are added to 1.25 g of N-[5-bromo-6-[4-(phenylmethoxy)phenyl]-1-[[2-(trimethylsilyl)ethoxy]methyl]-1H-indazol-3-yl]butanamide, prepared in Example 63, in 125 cm3 of dioxane, and the mixture is refluxed for 18 hours, 611 mg of 2-furan-2-yl-4,4,5,5-tetramethyl[1,3,2]dioxaborolane are then added and heating is continued for 4 hours at reflux. 75 cm3 of ethyl acetate and 75 cm3 of water are added and the reaction medium is filtered through a sinter funnel packed with Celite. The organic phase is separated out after settling of the phases has taken place, washed with 75 cm3 of water, dried over magnesium sulphate, filtered and concentrated to dryness under reduced pressure (2 kPa; 50 C.) to give 2 g of an oil, which is purified by chromatography under an argon pressure of 50 kPa, on a column of silica gel (particle size 40-60 mum; diameter 3.5 cm), eluting with a cyclohexane/ethyl acetate mixture (75/25 by volume). The fractions containing the expected product are combined and evaporated under reduced pressure (2 kPa; 50 C.) to give 1.20 g of N-[5-(2-furyl)-6-[4-(phenylmethoxy)phenyl]-1-[[2-(trimethylsilyl)ethoxy]methyl]-1H-indazol-3-yl]butanamide in the form of a beige-coloured solid. [0886] 1H NMR spectrum (300 MHz, (CD3)2SO-d6, delta in ppm): -0.09 (s: 9H); 0.82 (t, J=8 Hz: 2H); 0.97 (t, J=7.5 Hz: 3H); 1.68 (mt: 2H); 2.43 (t, J=7 Hz: 2H); 3.55 (t, J=8 Hz: 2H); 5.17 (s: 2H); 5.61 (d, J=3.5 Hz: 1H); 5.68 (broad s: 2H); 6.38 (dd, J=3.5 and 1.5 Hz: 1H); 7.07 (d, J=8.5 Hz: 2H); 7.19 (d, J=8.5 Hz: 2H); 7.36 (broad t, J=7.5 Hz: 1H); 7.43 (broad t, J=7.5 Hz: 2H); 7.50 (broad d, J=7.5 Hz: 2H); 7.59 (s: 1H); 7.61 (d, J=1.5 Hz: 1H); 8.20 (s: 1H); 10.58 (unresolved peak: 1H). [TABLE-US-00057] EI m/z = 581M+. m/z = 464[M - OCH2CH2Si(CH3)3]+ m/z = 91[C6H5CH2]+

References: [1]Patent: US2004/14802,2004,A1 .Location in patent: Page/Page column 55-56.

9
[ 374790-93-9 ]
[ 74-88-4 ]
[ 534-22-5 ]

References: [1]Chemistry - A European Journal,2009,vol. 15,p. 4165 - 4171.

10
[ 110-00-9 ]
[ 61676-62-8 ]
[ 374790-93-9 ]

References: [1]Chemistry - A European Journal,2009,vol. 15,p. 12978 - 12992.

11
[ 33948-35-5 ]
[ 374790-93-9 ]
[ 78210-65-8 ]

References: [1]Chemistry - A European Journal,2009,vol. 15,p. 12978 - 12992.

12
[ 14210-25-4 ]
[ 374790-93-9 ]
[ 332176-11-1 ]

References: [1]Tetrahedron Letters,2010,vol. 51,p. 3473 - 3476.

13
[ 1025719-99-6 ]
[ 374790-93-9 ]
[ 1080641-08-2 ]

Yield	Reaction Conditions	Operation in experiment
52%	With potassium carbonate;tetrakis(triphenylphosphine) palladium(0); In 1,2-dimethoxyethane; water; at 80℃; for 3h;	(R)-Methyl 2-(7-iododibenzo[b,d]furan-2-sulfonamido)-3-methylbutanoate (200 mg, 0.41 mmol) was mixed with <strong>[374790-93-9]2-(furan-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane</strong> (238 mg, 1.23 mmol), Pd(PPh3)4 (24 mg, 0.02 mmol), and K2CO3 (283 mg, 2.05 mmol) in 2 mL of DME and 0.5 mL of water. The reaction mixture was heated to 80 C. for 3 hours, and was diluted with ethyl acetate and water. The organic layer was separated and concentrated to give the crude product, which was purified by a preparative HPLC to yield (R)-methyl 2-(7-(furan-2-yl) dibenzo[b,d]furan-2-sulfonamido)-3-methylbutanoate (52% yield).

References: [1]Patent: US2010/227859,2010,A1 .Location in patent: Page/Page column 28.

14
[ 1080641-96-8 ]
[ 374790-93-9 ]
[ 1080642-02-9 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium phosphate;dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; In water; N,N-dimethyl-formamide; at 80℃; for 3h;	A mixture of (R)-methyl 2-(7-iododibenzo[b,d]thiophene-2-sulfonamido)-3-methylbutanoate (400 mg, 0.8 mmol) (an intermediate in the preparation of Example 30), <strong>[374790-93-9]2-(furan-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane</strong> (310 mg, 1.6 mmol), PdCl2(dppf).CH2Cl2 (68 mg, 0.08 mmol), K3PO4 (2 M solution in water) (2.4 mL) and DMF (16 mL), were heated at 80 C. for 3 hours. After cooling to RT, the mixture was poured into ethyl acetate and water, the organic layer was separated, concentrated under reduced pressure, and the crude residue was purified by preparative HPLC to yield (R)-methyl 2-(7-(furan-2-yl)dibenzo[b,d]thiophene-2-sulfonamido)-3-methylbutanoate (146.5 mg).

References: [1]Patent: US2010/227859,2010,A1 .Location in patent: Page/Page column 80.

15
[ 133038-74-1 ]
[ 374790-93-9 ]
(R)-2-(1-(furan-2-yl)-1-phenylethyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane [ No CAS ]

References: [1]Journal of the American Chemical Society,2010,vol. 132,p. 17096 - 17098.
[2]Journal of the American Chemical Society,2010,vol. 132,p. 17096 - 17098.

16
[ 77-85-0 ]
[ 374790-93-9 ]
C₄H₃OB(OCH₂)3CCH₃^(1-)*Na⁽¹⁺⁾=NaC₄H₃OB(OCH₂)3CCH₃ [ No CAS ]

References: [1]Chemistry Letters,2011,vol. 40,p. 702 - 704.

17
[ 110-00-9 ]
[ 25015-63-8 ]
[ 374790-93-9 ]

References: [1]Science,2015,vol. 349,p. 513 - 516.
[2]Chemistry - An Asian Journal,2010,vol. 5,p. 1657 - 1666.

18
[ 110-00-9 ]
[ 25015-63-8 ]
[ 374790-93-9 ]
2,5-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)furan [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
76%; 24%	With (CyAPDI)CoCH3; In neat (no solvent); at 23℃; for 10h;	EXAMPLE 9 - Borylation of Aromatic Five-Membered Heterocycle According to the reaction scheme illustrated in Figure 2(a), a scintillation vial (with a magnetic stir bar) was charged with cobalt complex (0.01 mmol) selected from 1-4, 2 methylfuran (1 mmol) and pinacolborane (1 mmol). The reaction was monitored by the analysis of an aliquot of the mixture by GC-FID. The mixture was allowed to stir to completion at room temperature and was quenched by exposure to air. The resulting solid was solubilized in CDC13, 1 ] 3 passed through a plug of silica gel in a Pasteur pipette and then analyzed by H and C NMR spectroscopy without further purification. If desired, the foregoing reaction can also be administered in 2 ml of tetrahydrofuran (THF). Figure 2(a) provides conversion percentages for cobalt complexes 1-4 with values in parenthesis as isolated yields. Further, Figure 2(b) details additional borylation products achieved with Co complexes 2 and 3 according to the foregoing reaction parameters.

References: [1]Patent: WO2015/89119,2015,A1 .Location in patent: Page/Page column 34.
[2]Chemistry - An Asian Journal,2010,vol. 5,p. 1657 - 1666.

19
[ 77-85-0 ]
[ 1310-73-2 ]
[ 374790-93-9 ]
C₄H₃OB(OCH₂)3CCH₃^(1-)*Na⁽¹⁺⁾=NaC₄H₃OB(OCH₂)3CCH₃ [ No CAS ]

References: [1]Chemistry Letters,2011,vol. 40,p. 702 - 704.

20
[ 19063-55-9 ]
[ 374790-93-9 ]
[ 1334143-28-0 ]

References: [1]Journal of Medicinal Chemistry,2011,vol. 54,p. 7055 - 7065.

21
[ 612-62-4 ]
[ 374790-93-9 ]
[ 4637-63-2 ]