Production Method 1

2404-35-5

73183-34-3

931583-43-6

Reaction Conditions

1.1 Reagents: Potassium tert-butoxide Catalysts: Cuprous chloride ,  1,1′-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis[1,1-diphenylphosphine] Solvents: Tetrahydrofuran ;  rt; overnight, rt

Reference

Photoredox-Catalyzed Cyclobutane Synthesis by a Deboronative Radical Addition-Polar Cyclization Cascade

Shu, Chao; Noble, Adam ; Aggarwal, Varinder K., Angewandte Chemie, 2019, 58(12), 3870-3874

Production Method 2

76-09-5

2404-35-5

931583-43-6

Reaction Conditions

1.1 Reagents: Sodium methoxide ,  2,2′-Bi-1,3,2-benzodioxaborole Catalysts: 4-Phenylpyridine Solvents: Acetonitrile ;  12 h, rt
1.2 Reagents: Triethylamine ;  1 h, rt
1.3 Solvents: Ethyl acetate ,  Water ;  rt

Reference

Photoinduced Radical Borylation of Alkyl Bromides Catalyzed by 4-Phenylpyridine

Zhang, Li; Wu, Zhong-Qian; Jiao, Lei, Angewandte Chemie, 2020, 59(5), 2095-2099

Production Method 3

2404-35-5

73183-34-3

931583-43-6

Reaction Conditions

1.1 Catalysts: Cupric chloride ,  1,1′-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis[1,1-diphenylphosphine] Solvents: Tetrahydrofuran ;  10 min, rt
1.2 Reagents: Potassium methoxide ;  30 min, rt
1.3 1 h, rt

Reference

Highly efficient synthesis of alkylboronate esters via Cu(II)-catalyzed borylation of unactivated alkyl bromides and chlorides in air

Bose, Shubhankar Kumar; Brand, Simon; Omoregie, Helen Oluwatola; Haehnel, Martin; Maier, Jonathan; et al, ACS Catalysis, 2016, 6(12), 8332-8335

Production Method 4

76-09-5

931583-43-6

Reaction Conditions

1.1 Reagents: 2,2′-Bi-1,3,2-benzodioxaborole Catalysts: 2,4,6-Tris(diphenylamino)-3,5-difluorobenzonitrile Solvents: Dimethylformamide ;  6 h, 20 °C
1.2 Reagents: Triethylamine ;  6 h, rt

Reference

Light-Mediated Sulfur-Boron Exchange

Panferova, Liubov I.; Dilman, Alexander D., Organic Letters, 2021, 23(10), 3919-3922

Production Method 5

76-09-5

14874-70-5

931583-43-6

Reaction Conditions

1.1 Reagents: 2,2′-Bi-1,3,2-benzodioxaborole Solvents: Dimethylacetamide ;  6 h, 30 °C
1.2 Reagents: Triethylamine ;  1 h, rt

Reference

Deaminative Borylation of Aliphatic Amines Enabled by Visible Light Excitation of an Electron Donor-Acceptor Complex

Sandfort, Frederik; Strieth-Kalthoff, Felix; Klauck, Felix J. R.; James, Michael J.; Glorius, Frank, Chemistry - A European Journal, 2018, 24(65), 17210-17214

Production Method 6

2404-35-5

73183-34-3

931583-43-6

Reaction Conditions

1.1 Reagents: Potassium tert-butoxide Catalysts: Cuprous chloride ,  1,1′-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis[1,1-diphenylphosphine] Solvents: Tetrahydrofuran ;  rt; overnight, rt

Reference

Divergent Aminocarbonylations of Alkynes Enabled by Photoredox/Nickel Dual Catalysis

Zhao, Xian; Feng, Xiaoliang; Chen, Fan; Zhu, Shengqing; Qing, Feng-Ling; et al, Angewandte Chemie, 2021, 60(51), 26511-26517

Production Method 7

2404-35-5

73183-34-3

931583-43-6

Reaction Conditions

1.1 Reagents: Lithium methoxide Catalysts: Copper oxide (Cu2O) Solvents: Ethanol ;  12 h, rt

Reference

Borylation of primary and secondary alkyl bromides catalyzed by Cu2O nanoparticles

Zhou, Xin-Feng; Wu, Ya-Dong; Dai, Jian-Jun; Li, Yong-Jia; Huang, Yu; et al, RSC Advances, 2015, 5(58), 46672-46676

Production Method 8

76-09-5

2404-35-5

931583-43-6

Reaction Conditions

1.1 Reagents: Azobisisobutyronitrile ,  Tris(trimethylsilyl)silane ,  2,2′-Bi-1,3,2-benzodioxaborole Solvents: Dimethylacetamide ;  6 h, 80 °C; 80 °C → rt
1.2 Reagents: Triethylamine ;  1 h, rt
1.3 Reagents: Tetrabutylammonium fluoride Solvents: Diethyl ether ,  Tetrahydrofuran ;  5 min, 0 °C

Reference

Transition metal- and light-free radical borylation of alkyl bromides and iodides using silane

Sun, Beiqi; Zheng, Sihan; Mo, Fanyang, Chemical Communications (Cambridge, 2021, 57(46), 5674-5677

Production Method 9

76-09-5

2404-35-5

931583-43-6

Reaction Conditions

1.1 Reagents: Tetrabutylammonium tetrafluoroborate ,  4,4,5,5-Tetramethyl-2-(3-phenylpropyl)-1,3,2-dioxaborolane Solvents: Dimethylacetamide ;  19 min, 25 °C
1.2 Reagents: Triethylamine ;  1 h, 25 °C
1.3 Reagents: Sodium chloride Solvents: Water

Reference

Electro-initiated preparation method of alkyl boride

, China, , ,

Production Method 10

76-09-5

2404-35-5

931583-43-6

Reaction Conditions

1.1 Reagents: Catecholborane ,  Potassium carbonate Catalysts: Titanocene dichloride Solvents: tert-Butyl methyl ether ;  30 min, 80 °C
1.2 24 h, 80 °C
1.3 Reagents: Triethylamine Solvents: tert-Butyl methyl ether ;  1 h, rt

Reference

Catalytic Boration of Alkyl Halides with Borane without Hydrodehalogenation Enabled by Titanium Catalyst

Wang, Xianjin ; Cui, Penglei; Xia, Chungu; Wu, Lipeng, Angewandte Chemie, 2021, 60(22), 12298-12303

Production Method 11

76-09-5

2404-35-5

931583-43-6

Reaction Conditions

1.1 Reagents: Catecholborane ,  Potassium carbonate Catalysts: Titanocene dichloride Solvents: tert-Butyl methyl ether ;  30 min, rt
1.2 24 h, 80 °C
1.3 Reagents: Triethylamine ;  1 h, rt

Reference

Method for directly preparing alkyl boronate compound from alkyl halide

, China, , ,

Production Method 12

2404-35-5

73183-34-3

931583-43-6

Reaction Conditions

1.1 Reagents: Ethylmagnesium bromide Catalysts: N,N,N′,N′-Tetramethylethylenediamine ,  Iron(III) acetylacetonate Solvents: Diethyl ether ,  Tetrahydrofuran ;  rt; 12 h, rt

Reference

Iron-Catalyzed Borylation of Alkyl Electrophiles

Atack, Thomas C.; Lecker, Rachel M.; Cook, Silas P., Journal of the American Chemical Society, 2014, 136(27), 9521-9523

Production Method 13

2404-35-5

73183-34-3

931583-43-6

Reaction Conditions

1.1 Reagents: Isobutanol ,  Potassium tert-butoxide Catalysts: 4,4′,4′′-Tris(1,1-dimethylethyl)-2,2′:6′,2′′-terpyridine ,  Dibromo[1,1′-(oxy-κO)bis[2-(methoxy-κO)ethane]]nickel Solvents: Diisopropyl ether ;  5 min, cooled
1.2 24 h, 60 °C

Reference

Alkylboronic Esters from Palladium- and Nickel-Catalyzed Borylation of Primary and Secondary Alkyl Bromides

Yi, Jun; Liu, Jin-Hui; Liang, Jun; Dai, Jian-Jun; Yang, Chu-Ting; et al, Advanced Synthesis & Catalysis, 2012, 354(9), 1685-1691

Production Method 14

2404-35-5

73183-34-3

931583-43-6

Reaction Conditions

1.1 Reagents: Lithium methoxide Catalysts: Triphenylphosphine ,  Cuprous iodide Solvents: Dimethylformamide ;  24 h, 37 °C

Reference

Alkylboronic Esters from Copper-Catalyzed Borylation of Primary and Secondary Alkyl Halides and Pseudohalides

Yang, Chu-Ting; Zhang, Zhen-Qi; Tajuddin, Hazmi; Wu, Chen-Cheng; Liang, Jun; et al, Angewandte Chemie, 2012, 51(2), 528-532

Production Method 15

2404-35-5

73183-34-3

931583-43-6

Reaction Conditions

1.1 Reagents: Lithium tert-butoxide Catalysts: Copper, compd. with palladium (2.8:0.2) (graphene supported) Solvents: Dimethylformamide ;  2 h, 30 °C

Reference

Visible-light-driven graphene supported Cu/Pd alloy nanoparticle-catalyzed borylation of alkyl bromides and chlorides in air

Jiao, Zhi-Feng; Tian, Ya-Ming ; Guo, Xiao-Ning ; Radius, Udo ; Braunschweig, Holger; et al, Journal of Catalysis, 2021, 395, 258-265

Production Method 16

2404-35-5

73183-34-3

931583-43-6

Reaction Conditions

1.1 Catalysts: Zinc chloride ,  1,3-Dihydro-1,3-bis(2,4,6-trimethylphenyl)-2H-imidazol-2-ylidene Solvents: tert-Butyl methyl ether ;  30 min, rt
1.2 Reagents: Potassium tert-butoxide ;  30 min, rt
1.3 1 h, rt

Reference

Zinc-Catalyzed Borylation of Primary, Secondary and Tertiary Alkyl Halides with Alkoxy Diboron Reagents at Room Temperature

Bose, Shubhankar Kumar; Fucke, Katharina; Liu, Lei; Steel, Patrick G.; Marder, Todd B., Angewandte Chemie, 2014, 53(7), 1799-1803

Production Method 17

76-09-5

2404-35-5

931583-43-6

Reaction Conditions

1.1 Reagents: Tris(trimethylsilyl)silane ,  2,2′-Bi-1,3,2-benzodioxaborole Catalysts: Azobisisobutyronitrile Solvents: Dimethylacetamide ;  6 h, 80 °C; 80 °C → rt
1.2 Reagents: Triethylamine ;  1 h, rt

Reference

Boron esterification reaction method catalyzed by alkyl bromide without transition metal

, China, , ,

Production Method 18

76-09-5

2453-46-5

931583-43-6

Reaction Conditions

1.1 Reagents: 2,2′-Bi-1,3,2-benzodioxaborole Catalysts: Zirconocene, dichloride ,  N,N′-Dicyclohexylurea ,  Iridium, tris[5-methoxy-2-(2-pyridinyl-κN)phenyl-κC]-, (OC-6-22)- Solvents: (Trifluoromethyl)benzene ;  12 h, 35 °C
1.2 Reagents: Triethylamine ;  1 h, 23 °C
1.3 Solvents: Water ;  23 °C

Reference

Chlorine Atom Transfer of Unactivated Alkyl Chlorides Enabled by Zirconocene and Photoredox Catalysis

Okita, Toshimasa; Aida, Kazuhiro; Tanaka, Keisuke; Ota, Eisuke ; Yamaguchi, Junichiro, Precision Chemistry, 2023, 1(2), 112-118

Production Method 19

76-09-5

2404-35-5

931583-43-6

Reaction Conditions

1.1 Reagents: Tetrabutylammonium tetrafluoroborate ,  Bis(pinacolato)diborane Solvents: Dimethylacetamide ;  19 min, 25 °C
1.2 Reagents: Triethylamine ;  1 h, 25 °C
1.3 Reagents: Sodium chloride Solvents: Water ;  25 °C

Reference

Electrochemical Borylation of Alkyl Halides: Fast, Scalable Access to Alkyl Boronic Esters

Wang, Bingbing; Peng, Pan; Ma, Wan; Liu, Zhao; Huang, Cheng; et al, Journal of the American Chemical Society, 2021, 143(33), 12985-12991

Production Method 20

73183-34-3

2404-36-6

931583-43-6

Reaction Conditions

1.1 Reagents: Lithium tert-butoxide Solvents: Methanol ,  Water ;  48 h, 50 °C

Reference

Transition-Metal-Free Borylation of Alkyl Iodides via a Radical Mechanism

Liu, Qianyi; Hong, Junting; Sun, Beiqi; Bai, Guangcan; Li, Feng; et al, Organic Letters, 2019, 21(17), 6597-6602

Cycloheptylboronic acid, pinacol ester Raw materials

• 2,3-Dimethylbutane-2,3-diol
• Bromocycloheptane
• Chlorocycloheptane
• Borate(1-),tetrafluoro-
• Bis(pinacolato)diborane
• Cycloheptane, iodo-

Cycloheptylboronic acid, pinacol ester Preparation Products

• Cycloheptylboronic acid, pinacol ester (931583-43-6)

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• 1073371-70-6(4,4,5,5-tetramethyl-2-[5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pentyl]-1,3,2-dioxaborolane)
• 66217-56-9(1,3,2-Dioxaborolane, 4,4,5,5-tetramethyl-2-octyl-)
• 200432-90-2(Heptyl, 1-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-)
• 1360914-08-4(2-cyclobutyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane)
• 86308-26-1(2-hexyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane)
• 126689-02-9(1,3,2-Dioxaborolane, 2-[(1R,2R)-2-butylcyclopropyl]-4,4,5,5-tetramethyl-, rel-)
• 200432-96-8(Pentyl, 1-[(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)methyl]-)
• 737776-93-1(Ferrocene,1,1'-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-)
• 66217-55-8(1,3,2-DIOXABOROLANE, 2-CYCLOPENTYL-4,4,5,5-TETRAMETHYL-)
• 87100-15-0(2-Cyclohexyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane)