Production Method 1

2113-56-6

25015-63-8

912844-88-3

Reaction Conditions

1.1 Reagents: Magnesium Catalysts: Cobalt chloride (CoCl2) ,  2,4,6-Trimethyl-N-[1-methyl-3-[(2,4,6-trimethylphenyl)amino]-2-buten-1-ylidene]b… Solvents: Tetrahydrofuran ;  24 h, 60 °C

Reference

Cobalt-Catalyzed Formation of Grignard Reagents via C-O or C-S Bond Activation

Pietrasiak, Ewa; Ha, Seongmin; Jeon, Seungwon; Jeong, Jongheon; Lee, Jiyeon; et al, Journal of Organic Chemistry, 2022, 87(13), 8380-8389

Production Method 2

73183-34-3

2367-22-8

912844-88-3

Reaction Conditions

1.1 Reagents: Lithium bis(trimethylsilyl)amide Catalysts: Tris(dibenzylideneacetone)dipalladium Solvents: Toluene ;  12 h, 80 °C

Reference

LiHMDS-Promoted Palladium or Iron-Catalyzed ipso-Defluoroborylation of Aryl Fluorides

Zhao, Xianghu; Wu, Mingsheng; Liu, Yisen; Cao, Song, Organic Letters, 2018, 20(18), 5564-5568

Production Method 3

2060541-04-8

912844-88-3

Reaction Conditions

1.1 Reagents: Triethylamine Catalysts: 1-Hydroxypyrene Solvents: Tetrahydrofuran ;  18 h, 35 °C

Reference

Bifunctional 1-Hydroxypyrene Photocatalyst for Hydrodesulfurization via Reductive C(Aryl)-S Bond Cleavage

Wu, Di; Shiozuka, Akira; Kawashima, Kyohei; Mori, Toshifumi ; Sekine, Kohei ; et al, Organic Letters, 2023, 25(18), 3293-3297

Production Method 4

73183-34-3

716-76-7

912844-88-3

Reaction Conditions

1.1 Reagents: Sodium fluoride ,  Proton sponge Catalysts: (SP-4-2)-Chlorotris(triphenylphosphine)rhodium ,  Methanaminium, N-[(dimethylamino)fluoromethylene]-N-methyl-, hexafluorophosphate… Solvents: Toluene ;  24 h, 140 °C

Reference

Rh-Catalyzed Direct Decarbonylative Borylation of Carboxylic Acids

Yin, Chang; Liao, Yanjing; He, Bangyue; Li, Hongyi; Su, Weiping, Chemistry - A European Journal, 2023, 29(29),

Production Method 5

73183-34-3

643-93-6

912844-88-3

Reaction Conditions

1.1 Reagents: N-Hydroxyphthalimide ,  tert-Butyl nitrite Catalysts: Lithium bromide Solvents: Acetonitrile ;  48 h, 80 °C
1.2 Catalysts: 1,1-Dimethylethyl 3-pyridinecarboxylate Solvents: (Trifluoromethyl)benzene ;  21 h, 110 °C

Reference

Cleavage of C(aryl)-CH3 Bonds in the Absence of Directing Groups under Transition Metal Free Conditions

Dai, Peng-Fei; Ning, Xiao-Shan; Wang, Hua; Cui, Xian-Chao; Liu, Jie; et al, Angewandte Chemie, 2019, 58(16), 5392-5395

Production Method 6

2051-61-8

73183-34-3

912844-88-3

Reaction Conditions

1.1 Reagents: Potassium tert-butoxide Catalysts: Iron(III) acetylacetonate Solvents: Toluene ;  16 h, 150 °C; 150 °C → rt
1.2 Reagents: Ammonium chloride Solvents: Water ;  rt

Reference

Iron-catalyzed borylation of aryl chlorides in the presence of potassium t-butoxide

Yoshida, Takumi; Ilies, Laurean; Nakamura, Eiichi, ACS Catalysis, 2017, 7(5), 3199-3203

Production Method 7

25015-63-8

912844-88-3

144432-80-4

Reaction Conditions

1.1 Catalysts: (SP-4-3)-Carbonylchlorobis(trimethylphosphine)rhodium ;  12 h
1.2 Reagents: Oxygen ;  5 min

Reference

Efficient Rh-catalyzed C-H borylation of arene derivatives under photochemical conditions

Bheeter, Charles Beromeo; Chowdhury, Abhishek Dutta; Adam, Rosa; Jackstell, Ralf; Beller, Matthias, Organic & Biomolecular Chemistry, 2015, 13(41), 10336-10340

Production Method 8

25015-63-8

912844-88-3

144432-80-4

Reaction Conditions

1.1 Catalysts: [[1,3-Bis[2,6-bis(1-methylethyl)phenyl]-2-phenyl-1H-imidazolium-4,5-diyl]-1,2-ph… ;  24 h, 100 °C

Reference

Nickel-Catalyzed C(sp2)-H Borylation of Arenes

Das, Arpan; Hota, Pradip Kumar; Mandal, Swadhin K., Organometallics, 2019, 38(17), 3286-3293

Production Method 9

76-09-5

5122-95-2

912844-88-3

Reaction Conditions

1.1 Solvents: Diethyl ether ;  overnight, rt

Reference

Palladium-Catalyzed Monofluoromethylation of Arylboronic Esters with Fluoromethyl Iodide

Hu, Jingyu; Gao, Bing; Li, Lingchun; Ni, Chuanfa; Hu, Jinbo, Organic Letters, 2015, 17(12), 3086-3089

Production Method 10

580-51-8

73183-34-3

912844-88-3

Reaction Conditions

1.1 Reagents: Tripotassium phosphate ,  Methanaminium, N-[(dimethylamino)fluoromethylene]-N-methyl-, hexafluorophosphate… Catalysts: Bis(1,5-cyclooctadiene)nickel ,  Tricyclohexylphosphine Solvents: 1,4-Dioxane ;  24 h, 60 °C

Reference

Ni-Catalyzed Deoxygenative Borylation of Phenols Via O-Phenyl-uronium Activation

Liu, Xiaojie; Xu, Biping; Su, Weiping, ACS Catalysis, 2022, 12(15), 8904-8910

Production Method 11

157790-83-5

73183-34-3

912844-88-3

Reaction Conditions

1.1 Reagents: Lithium tert-butoxide Catalysts: Bis(acetylacetonato)nickel ,  1H-Imidazolium, 1,3-bis[2,6-bis(1-methylethyl)phenyl]-4,5-dimethyl-, chloride (1… Solvents: Cyclopentyl methyl ether ;  16 h, 100 °C

Reference

Nickel-Catalyzed Ipso-Borylation of Silyloxyarenes via C-O Bond Activation

Pein, Wesley L. ; Wiensch, Eric M.; Montgomery, John, Organic Letters, 2021, 23(12), 4588-4592

Production Method 12

73183-34-3

2367-22-8

912844-88-3

Reaction Conditions

1.1 Reagents: Cesium fluoride Catalysts: Chlorobis(tricyclohexylphosphine)copper Solvents: Toluene ;  24 h, 80 °C

Reference

Copper-Catalyzed ipso-Borylation of Fluoroarenes

Niwa, Takashi ; Ochiai, Hidenori; Hosoya, Takamitsu, ACS Catalysis, 2017, 7(7), 4535-4541

Production Method 13

73183-34-3

2113-57-7

912844-88-3

Reaction Conditions

1.1 Reagents: Potassium acetate Catalysts: [1,1′-Bis(diphenylphosphino)ferrocene]dichloropalladium ,  2′-(Dicyclohexylphosphino)-N,N-dimethyl[1,1′-biphenyl]-2-amine ;  3 h

Reference

Electromagnetic Mill Promoted Mechanochemical Solvent-Free Palladium-Catalyzed Borylation of Aryl Bromides

Liu, Yunxia; Li, Xin; Liu, Qing ; Li, Xinjin ; Liu, Hui, Organic Letters, 2022, 24(36), 6604-6608

Production Method 14

73183-34-3

2113-57-7

912844-88-3

Reaction Conditions

1.1 Reagents: Potassium acetate Catalysts: Dichloro[1,1′-bis(diphenylphosphino)ferrocene]palladium(II) dichloromethane addu… Solvents: 1,4-Dioxane ;  24 h, reflux

Reference

Ligand-Enabled, Iridium-Catalyzed ortho-Borylation of Fluoroarenes

Kuleshova, Olena; Asako, Sobi ; Ilies, Laurean, ACS Catalysis, 2021, 11(10), 5968-5973

Production Method 15

73183-34-3

912844-88-3

144432-80-4

Reaction Conditions

1.1 Catalysts: 2411767-15-0 ;  20 h, 120 °C

Reference

Undirected ortho-selectivity in C-H borylation of arenes catalyzed by NHC platinum(0) complexes

Rzhevskiy, Sergey A.; Topchiy, Maxim A.; Golenko, Yulia D.; Gribanov, Pavel S.; Sterligov, Grigorii K.; et al, Mendeleev Communications, 2020, 30(5), 569-571

Production Method 16

73183-34-3

716-76-7

912844-88-3

Reaction Conditions

1.1 Catalysts: Pyridine ,  Tetrabutylammonium acetate ,  2,8-Dichloroindolo[2,1-b]quinazoline-6,12-dione Solvents: Acetone ,  Acetonitrile ;  6 h, 35 - 40 °C

Reference

Organic charge-transfer complex induces chemoselective decarboxylation to aryl radicals for general functionalization

Hu, Chun-Hong; Sang, Yueqian; Yang, Ya-Wei; Li, Wen-Wen; Wang, Hui-Lin; et al, Chem, 2023, 9(10), 2997-3012

Production Method 17

2244150-61-4

73183-34-3

912844-88-3

Reaction Conditions

1.1 Catalysts: Triphenylphosphine ,  Bis(1,5-cyclooctadiene)nickel Solvents: Toluene ,  Octane ;  30 s, rt
1.2 Reagents: Sodium chloride ,  Potassium fluoride ;  24 h, 140 °C

Reference

Nickel-catalyzed decarbonylative borylation of aroyl fluorides

Wang, Zhenhua; Wang, Xiu; Nishihara, Yasushi, Chemical Communications (Cambridge, 2018, 54(99), 13969-13972

Production Method 18

2052-07-5

73183-34-3

912844-88-3

Reaction Conditions

1.1 Reagents: Potassium acetate Catalysts: [1,1′-Bis(diphenylphosphino)ferrocene]dichloropalladium Solvents: 1,4-Dioxane ;  18 h, reflux

Reference

Fluorine-programmed nanozipping to tailored nanographenes on rutile TiO2 surfaces

Kolmer, M. ; Zuzak, R. ; Steiner, A. K. ; Zajac, L. ; Engelund, M. ; et al, Science (Washington, 2019, 363(6422), 57-60

Production Method 19

1997317-90-4

73183-34-3

912844-88-3

Reaction Conditions

1.1 Reagents: Lithium carbonate (Li2CO3) Catalysts: Tributylphosphine ,  Bis(1,5-cyclooctadiene)nickel Solvents: 1,4-Dioxane ;  36 h, 170 °C

Reference

Functional Group Interconversion: Decarbonylative Borylation of Esters for the Synthesis of Organoboronates

Guo, Lin; Rueping, Magnus, Chemistry - A European Journal, 2016, 22(47), 16787-16790

Production Method 20

2243-47-2

73183-34-3

912844-88-3

Reaction Conditions

1.1 Reagents: Oxygen Catalysts: Acridinium, 10-methyl-9-(2,4,6-trimethylphenyl)-, tetrafluoroborate(1-) (1:1) Solvents: Dimethyl carbonate ;  24 h, 35 °C

Reference

Photoinduced Divergent Deaminative Borylation and Hydrodeamination of Primary Aromatic Amines

Shiozuka, Akira; Sekine, Kohei ; Toki, Takumi; Kawashima, Kyohei; Mori, Toshifumi ; et al, Organic Letters, 2022, 24(23), 4281-4285

Production Method 21

73183-34-3

912844-88-3

Reaction Conditions

1.1 Reagents: Potassium acetate Catalysts: [1,1′-Bis(diphenylphosphino)ferrocene]dichloropalladium Solvents: 1,4-Dioxane ;  12 h, 120 °C

Reference

Metal-Free and Redox-Neutral Conversion of Organotrifluoroborates into Radicals Enabled by Visible Light

Liu, Wenbo ; Liu, Peng; Lv, Leiyang; Li, Chao-Jun, Angewandte Chemie, 2018, 57(41), 13499-13503

Production Method 22

73183-34-3

912844-88-3

144432-80-4

Reaction Conditions

1.1 Catalysts: 2756816-84-7 ;  72 h, 110 °C

Reference

Rhodium Indenyl NHC and Fluorenyl-Tethered NHC Half-Sandwich Complexes: Synthesis, Structures and Applications in the Catalytic C-H Borylation of Arenes and Alkanes

Evans, Kieren J. ; Morton, Paul A. ; Luz, Christian; Miller, Callum; Raine, Olivia; et al, Chemistry - A European Journal, 2021, 27(71), 17824-17833

2-([1,1'-Biphenyl]-3-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane Raw materials

• 2,3-Dimethylbutane-2,3-diol
• 3-Methoxybiphenyl
• 3-Phenylphenol
• 4,4,5,5-Tetramethyl-2-[4-(methylthio)[1,1′-biphenyl]-3-yl]-1,3,2-dioxaborolane
• Carbamic acid, diethyl-, [1,1'-biphenyl]-3-yl ester
• 3-Aminobiphenyl
• 2-Bromo-1,1'-biphenyl
• 3-Chlorobiphenyl
• [1,1'-Biphenyl]-3-carbonyl fluoride
• Phenyl [1,1'-biphenyl]-3-carboxylate
• Bis(pinacolato)diborane
• Pinacolborane
• 3-Bromobiphenyl
• 3-Biphenylboronic acid
• 1,1'-biphenyl-3-carboxylic acid
• 3-Methyl-1,1'biphenyl
• 3-Fluorobiphenyl

2-([1,1'-Biphenyl]-3-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane Preparation Products

• 4-Biphenylboronic acid pinacol ester (144432-80-4)
• 2-([1,1'-Biphenyl]-3-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (912844-88-3)

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  RabailGul,MariamMir,MurtazaNAli
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  Christian K. Rank,Alexander W. Jones,Tatjana Wall,Patrick Di Martino-Fumo,Sarah Schr?ck,Markus Gerhards,Frederic W. Patureau Chem. Commun., 2019,55, 13749-13752
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• Other Chemical Reagents Derivatization Reagents
• Solvents and Organic Chemicals Organic Compounds Acids/Esters

• 144432-80-4(4-Biphenylboronic acid pinacol ester)
• 1036378-83-2(1,3,2-Dioxaborolane, 4,4,5,5-tetramethyl-2-[1,1':3',1''-terphenyl]-5'-yl-)
• 207611-87-8(4,4'-Bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,1'-biphenyl)
• 1115023-84-1(2-([1,1':3',1''-Terphenyl]-3-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane)
• 1381960-58-2(4,4,5,5-Tetramethyl-2-4-(4-methylphenyl)phenyl-1,3,2-dioxaborolane)
• 1017967-97-3(2,2'-(5'-(4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-[1,1':3',1''-terphenyl]-4,4''-diyl)bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane))
• 1080632-76-3(2-([1,1':4',1''-Terphenyl]-4-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane)
• 1923743-78-5(4,4,5,5-tetramethyl-2-{5-methyl-1,1'-biphenyl-3-yl}-1,3,2-dioxaborolane)
• 1115639-92-3(4,4,5,5-Tetramethyl-2-(3-(triphenylen-2-yl)phenyl)-1,3,2-dioxaborolane)
• 1263272-83-8(4,4,5,5-Tetramethyl-2-(3-(naphthalen-1-yl)phenyl)-1,3,2-dioxaborolane)