Production Method 1

73183-34-3

6746-94-7

849061-99-0

Reaction Conditions

1.1 Reagents: Sodium methoxide Catalysts: Copper Solvents: Ethanol ;  24 h, rt

Reference

Cu-Catalyzed C-H Alkenylation of Benzoic Acid and Acrylic Acid Derivatives with Vinyl Boronates

Li, Jian-Jun; Wang, Cheng-Gang; Yu, Jin-Feng; Wang, Peng ; Yu, Jin-Quan, Organic Letters, 2020, 22(12), 4692-4696

Production Method 2

25015-63-8

6746-94-7

849061-99-0

Reaction Conditions

1.1 Catalysts: Sodium tert-butoxide ,  2255360-50-8 Solvents: Toluene ;  16 h, 80 °C
1.2 Reagents: Sodium bicarbonate Solvents: Water

Reference

Dearomatization and Functionalization of Terpyridine Ligands Leading to Unprecedented Zwitterionic Meisenheimer Aluminum Complexes and Their Use in Catalytic Hydroboration

Zhang, Guoqi ; Wu, Jing; Zeng, Haisu; Neary, Michelle C. ; Devany, Matthew; et al, ACS Catalysis, 2019, 9(2), 874-884

Production Method 3

73183-34-3

6746-94-7

849061-99-0

Reaction Conditions

1.1 Reagents: Sodium methoxide Catalysts: Copper Solvents: Ethanol ;  11 h, 25 °C

Reference

Ligand-free hydroboration of alkynes catalyzed by heterogeneous copper powder with high efficiency

Zhao, Jie; Niu, Zhiqiang; Fu, Hua; Li, Yadong, Chemical Communications (Cambridge, 2014, 50(16), 2058-2060

Production Method 4

25015-63-8

6746-94-7

849061-99-0

Reaction Conditions

1.1 Reagents: Dabco Catalysts: Methanesulfonic acid, 1,1,1-trifluoro-, iron(2+) salt (2:1) Solvents: Toluene ;  72 h, 100 °C

Reference

Iron-Catalyzed Dehydrogenative Borylation of Terminal Alkynes

Wei, Duo; Carboni, Bertrand; Sortais, Jean-Baptiste; Darcel, Christophe, Advanced Synthesis & Catalysis, 2018, 360(19), 3649-3654

Production Method 5

25015-63-8

6746-94-7

849061-99-0

Reaction Conditions

1.1 Catalysts: Tris(pentafluorophenyl)borane Solvents: Toluene ;  rt; 2 h, 60 °C

Reference

Zwitterion-Initiated Hydroboration of Alkynes and Styrene

Bismuto, Alessandro ; Cowley, Michael J. ; Thomas, Stephen P., Advanced Synthesis & Catalysis, 2021, 363(9), 2382-2385

Production Method 6

25015-63-8

6746-94-7

849061-99-0

Reaction Conditions

1.1 Catalysts: Aluminum, dihydro[N,N′,N′′,N′′′-tetrakis(2,6-diethylphenyl)imidodicarbonimidic d… ;  12 h, 60 °C

Reference

Aluminum-Catalyzed Selective Hydroboration of Nitriles and Alkynes: A Multifunctional Catalyst

Sarkar, Nabin; Bera, Subhadeep; Nembenna, Sharanappa, Journal of Organic Chemistry, 2020, 85(7), 4999-5009

Production Method 7

25015-63-8

6746-94-7

849061-99-0

Reaction Conditions

1.1 Catalysts: (T-4)-[[N,N′-(1,3-Dimethyl-1,3-propanediylidene)bis[2,6-diethylbenzenaminato-κN]… ;  32 h, 30 °C

Reference

An Aluminum Dihydride Working as a Catalyst in Hydroboration and Dehydrocoupling

Yang, Zhi; Zhong, Mingdong; Ma, Xiaoli; Nijesh, Karikkeeriyil; De, Susmita; et al, Journal of the American Chemical Society, 2016, 138(8), 2548-2551

Production Method 8

25015-63-8

6746-94-7

849061-99-0

Reaction Conditions

1.1 Catalysts: 2765810-19-1 Solvents: 1,2-Difluorobenzene ;  10 min, 90 °C
1.2 20 h, 90 °C

Reference

An "On-Demand", Selective Dehydrogenative Borylation or Hydroboration of Terminal Alkynes Using Zn2+-based Catalyst

Jaiswal, Kuldeep ; Groutchik, Kristina; Bawari, Deependra ; Dobrovetsky, Roman, ChemCatChem, 2022, 14(9),

Production Method 9

25015-63-8

6746-94-7

849061-99-0

Reaction Conditions

1.1 Catalysts: Potassium tert-butoxide ,  Cobalt, dichloro[4′-(4-pyridinyl)-2,2′:6′,2′′-terpyridine-κN1,κN1′,κN1′′]-, (SP-… Solvents: Tetrahydrofuran ;  1 min, rt
1.2 5 min, rt
1.3 Reagents: Dichloromethane

Reference

Highly efficient and selective hydroboration of terminal and internal alkynes catalyzed by a cobalt(II) coordination polymer

Zhang, Guoqi; Li, Sihan; Wu, Jing; Zeng, Haisu; Mo, Zixuan; et al, Organic Chemistry Frontiers, 2019, 6(18), 3228-3233

Production Method 10

25015-63-8

6746-94-7

849061-99-0

Reaction Conditions

1.1 Catalysts: Vanadium, [1′,4′-dihydro-4′-[(trimethylsilyl)methyl]-2,2′:6′,2′′-terpyridine-κN1… Solvents: Diethyl ether ;  16 h, rt

Reference

Vanadium-Catalyzed Stereo- and Regioselective Hydroboration of Alkynes to Vinyl Boronates

Zhang, Guoqi ; Zeng, Haisu; Zheng, Shengping ; Neary, Michelle C. ; Dub, Pavel A., ACS Catalysis, 2022, 12(9), 5425-5429

Production Method 11

25015-63-8

6746-94-7

849061-99-0

Reaction Conditions

1.1 Catalysts: 9-Borabicyclo[3.3.1]nonane Solvents: Tetrahydrofuran ;  2 h, rt

Reference

Kinetics and Mechanism of the Arase-Hoshi R2BH-Catalyzed Alkyne Hydroboration: Alkenylboronate Generation via B-H/C-B Metathesis

Nieto-Sepulveda, Eduardo; Bage, Andrew D.; Evans, Louise A. ; Hunt, Thomas A.; Leach, Andrew G. ; et al, Journal of the American Chemical Society, 2019, 141(46), 18600-18611

Production Method 12

73183-34-3

6746-94-7

849061-99-0

Reaction Conditions

1.1 Catalysts: N-Propyl-N-[2-(2-pyridinylamino)phenyl]formamide Solvents: Water ;  12 h, 50 °C

Reference

Aqueous hydroboration of alkynes via nonclassical generation of N-heterocyclic carbenes

Tao, Sheng; Wang, Yang; Pan, Qianxiu; Zhao, Jixing; Bu, Qingqing; et al, Green Chemistry, 2023, 25(17), 6704-6716

Production Method 13

73183-34-3

6746-94-7

849061-99-0

Reaction Conditions

1.1 Reagents: Sodium methoxide ,  Oxygen Catalysts: Copper iron oxide (CuFe2O4) (copper supported) Solvents: Ethanol ;  2 h, 22 °C

Reference

Efficient heterogeneous hydroboration of alkynes: enhancing the catalytic activity by Cu(0) incorporated CuFe2O4 nanoparticles

Zeng, Xianghua; Gong, Chunhua; Guo, Haiyang; Xu, Hao; Zhang, Junyong; et al, New Journal of Chemistry, 2018, 42(21), 17346-17350

Production Method 14

25015-63-8

6746-94-7

849061-99-0

Reaction Conditions

1.1 Reagents: Triethylamine Catalysts: Zirconocene chloride hydride ;  16 h, 60 °C

Reference

Preparation of α-Imino Aldehydes by [1,3]-Rearrangements of O-Alkenyl Oximes

Kontokosta, Dimitra; Mueller, Daniel S.; Wang, Heng-Yen; Anderson, Laura L., Organic Letters, 2013, 15(18), 4830-4833

Production Method 15

25015-63-8

6746-94-7

849061-99-0

Reaction Conditions

1.1 Catalysts: Sodium triethylborohydride ,  2770537-52-3 Solvents: Tetrahydrofuran ,  tert-Butyl methyl ether ;  10 h, 45 °C

Reference

Integrating Terminal CoBrn Salts into a 2D Cobalt(II) Coordination Polymer to Promote the β-(E)-Selective Hydroboration of Alkynes

Jia, Jun-Song; Wu, Tai-Xue; Fu, Yi-Jia; Hu, Zhi-Rong; Tang, Hai-Tao ; et al, Advanced Synthesis & Catalysis, 2022, 364(11), 1873-1878

Production Method 16

25015-63-8

6746-94-7

849061-99-0

Reaction Conditions

1.1 Catalysts: (T-4)-Trihydro(tetrahydrofuran)boron Solvents: Tetrahydrofuran ;  1 h, 60 °C
1.2 Solvents: Dichloromethane

Reference

Borane-Catalyzed Hydroboration of Alkynes and Alkenes

Ang, Nate W. J.; Buettner, Cornelia S.; Docherty, Scott; Bismuto, Alessandro; Carney, Jonathan R.; et al, Synthesis, 2018, 50(4), 803-808

Production Method 17

73183-34-3

6746-94-7

849061-99-0

Reaction Conditions

1.1 Reagents: Potassium tert-butoxide ,  Oxygen Catalysts: Copper iron oxide (CuFe2O4) Solvents: Methanol ;  12 h, 50 °C

Reference

Superparamagnetic copper ferrite nanoparticles catalyzed aerobic, ligand-free, regioselective hydroboration of alkynes: Influence of synergistic effect

Mohan, Balaji; Park, Kang Hyun, Applied Catalysis, 2016, 519, 78-84

(E)-2-Cyclopropylvinylboronic acid pinacol ester Raw materials

• Bis(pinacolato)diborane
• Pinacolborane
• Cyclopropylacetylene

(E)-2-Cyclopropylvinylboronic acid pinacol ester Preparation Products

• (E)-2-Cyclopropylvinylboronic acid pinacol ester (849061-99-0)

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• Solvents and Organic Chemicals Organic Compounds Organic acids and derivatives Boronic acid derivatives Boronic acid esters
• Other Chemical Reagents Derivatization Reagents
• Solvents and Organic Chemicals Organic Compounds Acids/Esters

• 83947-55-1(trans-4,4,5,5-Tetramethyl-2-oct-1-enyl-1,3,2-dioxaborolane)
• 170942-79-7(TRANS-4,4,5,5-TETRAMETHYL-2-OCT-1-ENYL-1,3,2-DIOXABOROLANE)
• 91083-23-7(1,3,2-Dioxaborolane, 2-(1-hexenyl)-4,4,5,5-tetramethyl-, (Z)-)
• 161395-96-6((E)-4,4,5,5-Tetramethyl-2-(pent-1-en-1-yl)-1,3,2-dioxaborolane)
• 169339-75-7(trans-1-Heptenylboronic Acid Pinacol Ester)
• 154820-94-7(1,3,2-Dioxaborolane,2-(1-hexen-1-yl)-4,4,5,5-tetramethyl-)
• 843612-43-1(1,3,2-Dioxaborolane,2-[(1E)-3,3-dimethyl-1-pentenyl]-4,4,5,5-tetramethyl-)
• 172512-85-5(2-(2-cyclohexylethenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane)
• 154820-99-2(2-t-Butyl-E-vinylboronic acid, pinacol ester)
• 126688-97-9(1,3,2-Dioxaborolane,2-(1E)-1-hexen-1-yl-4,4,5,5-tetramethyl-)