87100-15-0 (环己烷硼酸频那醇酯,2-Cyclohexyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane)

_100%

反应条件：

1.1 Reagents: Potassium carbonate Solvents: 1,4-Dioxane ; 5 h, 100 °C; 100 °C → rt
1.2 10 min, 100 °C

参考文献：

A practical and modular construction of C(sp3)-rich alkyl boron compounds

Yang, Yangyang; et al, ChemRxiv, 2020, 1, 1-9

合成路线：1 步

4441-56-9

_96%

反应条件：

1.1 3 h, rt

参考文献：

Hydrogenation of Borylated Arenes

Wollenburg, Marco; et al, Angewandte Chemie, 2019, 58(20), 6549-6553

合成路线：1 步

4441-56-9

_90%

反应条件：

1.1 Reagents: Sulfuric acid magnesium salt (1:1) Solvents: Diethyl ether ; 16 h, rt

参考文献：

Synthesis of 3-Aryl-1-aminopropane Derivatives: Lithiation-Borylation-Ring-Opening of Azetidinium Ions

Casoni, Giorgia; et al, Synthesis, 2016, 48(19), 3241-3253

合成路线：1 步

_99%

反应条件：

1.1 Reagents: Potassium methoxide Catalysts: Copper Solvents: Dimethylformamide ; 1 h, rt

参考文献：

Facile synthesis of alkyl- and arylboronate esters enabled by a carbon nanotube supported copper catalyst

Saini, Suresh; et al, Catalysis Science & Technology, 2023, 13(1), 147-156

合成路线：1 步

_99%

反应条件：

1.1 Catalysts: (T-4)-Chlorotris(triphenylphosphine)cobalt , 1,3-Dicyclohexyl-1,3-dihydro-2H-imidazol-2-ylidene Solvents: tert-Butyl methyl ether ; 0.5 h, rt
1.2 Reagents: Sodium ethoxide ; 16 h, 50 °C
1.3 Reagents: Oxygen

参考文献：

Cobalt(I)-Catalyzed Borylation of Unactivated Alkyl Bromides and Chlorides

Verma, Piyush Kumar; et al, Organic Letters, 2020, 22(4), 1431-1436

合成路线：1 步

_99%

反应条件：

1.1 Reagents: Potassium tert-butoxide Catalysts: Dopamine (anchored on ferrite) , Copper (nano-Fe-DOPA supported) Solvents: Dimethylformamide ; 18 h, rt

参考文献：

Efficient synthesis of alkylboronic esters via magnetically recoverable copper nanoparticle-catalyzed borylation of alkyl chlorides and bromides

Shegavi, Mahadev L.; et al, Green Chemistry, 2020, 22(9), 2799-2803

合成路线：1 步

24388-23-6

_99%

反应条件：

1.1 Reagents: Hydrogen Catalysts: [1-[2,6-Bis(1-methylethyl)phenyl]-3,3,5,5-tetramethyl-2-pyrrolidinylidene]chloro… Solvents: 2,2,2-Trifluoroethanol ; 24 h, 5 MPa, rt

参考文献：

Hydrogenation of (Hetero)aryl Boronate Esters with a Cyclic (Alkyl)(amino)carbene-Rhodium Complex: Direct Access to cis-Substituted Borylated Cycloalkanes and Saturated Heterocycles

Ling, Liang; et al, Angewandte Chemie, 2019, 58(20), 6554-6558

合成路线：1 步

24388-23-6

_82%

反应条件：

1.1 Reagents: Pinacol , Diboronic acid Catalysts: Bis[(1,2,5,6-η)-1,5-cyclooctadiene]di-μ-hydroxydirhodium Solvents: Ethanol ; 18 h, 50 °C

参考文献：

Mild and Selective Rhodium-Catalyzed Transfer Hydrogenation of Functionalized Arenes

Wang, Yuhan; et al, Organic Letters, 2021, 23(5), 1910-1914

合成路线：1 步

_99%

反应条件：

1.1 Reagents: Potassium tert-butoxide Catalysts: Dopamine (anchored on ferrite) , Copper (nano-Fe-DOPA supported) Solvents: Dimethylformamide ; 18 h, rt

参考文献：

Efficient synthesis of alkylboronic esters via magnetically recoverable copper nanoparticle-catalyzed borylation of alkyl chlorides and bromides

Shegavi, Mahadev L.; et al, Green Chemistry, 2020, 22(9), 2799-2803

合成路线：1 步

_96%

反应条件：

1.1 Reagents: Potassium methoxide Catalysts: Copper Solvents: Dimethylformamide ; 1 h, rt

参考文献：

Facile synthesis of alkyl- and arylboronate esters enabled by a carbon nanotube supported copper catalyst

Saini, Suresh; et al, Catalysis Science & Technology, 2023, 13(1), 147-156

合成路线：1 步

_86%

反应条件：

1.1 Reagents: 2,2′-Bi-1,3,2-benzodioxaborole Solvents: Dimethylformamide ; 24 h, rt
1.2 Reagents: Triethylamine ; 1 h, rt

参考文献：

Metal-Free Radical Borylation of Alkyl and Aryl Iodides

Cheng, Ying; et al, Angewandte Chemie, 2018, 57(51), 16832-16836

合成路线：1 步

_97%

反应条件：

1.1 Catalysts: Bis(dichloro(η6-p-cymene)ruthenium) ; 24 h, rt

参考文献：

Ruthenium-Catalyzed Anti-Markovnikov Selective Hydroboration of Olefins

Kisan, Sesha; et al, ACS Catalysis, 2017, 7(9), 5950-5954

合成路线：1 步

_95%

反应条件：

1.1 Catalysts: 2839130-42-4 ; 12 h, 100 °C

参考文献：

Monomeric Magnesium Catalyzed Alkene and Alkyne Hydroboration

Kumar, Rohit; et al, Chemistry - A European Journal, 2022, 28(56),

合成路线：1 步

_94%

反应条件：

1.1 Catalysts: 1,2-Bis(diphenylphosphino)ethane , Di-μ-chlorobis[(1,2,5,6-η)-1,5-cyclooctadiene]diiridium Solvents: Dichloromethane ; 0 °C; 16 h, rt
1.2 Reagents: Methanol , Water ; rt

参考文献：

A General Approach to Deboronative Radical Chain Reactions with Pinacol Alkylboronic Esters

Andre-Joyaux, Emy; et al, Angewandte Chemie, 2020, 59(33), 13859-13864

合成路线：1 步

2101752-79-6

_95%

反应条件：

1.1 Catalysts: 1,10-Phenanthroline , Cuprous iodide Solvents: Acetonitrile ; 0.5 h, 50 °C; 50 °C → rt

参考文献：

Synthesis of Functionalized Organoboron/Silicon Compounds by Copper-Catalyzed Coupling of Alkylsilyl Peroxides and Diboron/Silylborane Reagents

Seihara, Takumi; et al, Organic Letters, 2019, 21(7), 2477-2481

合成路线：1 步

_86%

反应条件：

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

参考文献：

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

Wang, Bingbing; et al, Journal of the American Chemical Society, 2021, 143(33), 12985-12991

合成路线：1 步

_72%

反应条件：

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

参考文献：

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

Sun, Beiqi; et al, Chemical Communications (Cambridge, 2021, 57(46), 5674-5677

合成路线：1 步

126812-30-4

_86%

反应条件：

1.1 Reagents: Tetrabutylammonium tetrafluoroborate , 2,2′-Bi-1,3,2-benzodioxaborole Solvents: Dimethylformamide ; 4 h, rt
1.2 Reagents: Triethylamine ; 2 h, rt

参考文献：

Electrochemically promoted decarboxylative borylation of alkyl N-hydroxyphthalimide esters

Dai, Jian-Jun ; et al, Chinese Chemical Letters, 2022, 33(3), 1555-1558

合成路线：1 步

_86%

反应条件：

1.1 Reagents: Tetrabutylammonium tetrafluoroborate , Bis(pinacolato)diborane Solvents: Dimethylformamide ; 12 min, 25 °C
1.2 Reagents: Triethylamine ; 1 h, 25 °C
1.3 Reagents: Sodium chloride Solvents: Water ; 25 °C

参考文献：

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

Wang, Bingbing; et al, Journal of the American Chemical Society, 2021, 143(33), 12985-12991

合成路线：1 步

1542422-29-6

_85%

反应条件：

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

参考文献：

Light-Mediated Sulfur-Boron Exchange

Panferova, Liubov I.; et al, Organic Letters, 2021, 23(10), 3919-3922

合成路线：1 步

542-18-7

_84%

反应条件：

1.1 Catalysts: Cupric chloride , 1,3-Bis[2,6-bis(1-methylethyl)phenyl]-1,3-dihydro-2H-imidazol-2-ylidene Solvents: Tetrahydrofuran ; 10 min, rt
1.2 Reagents: Potassium methoxide ; 10 min, rt
1.3 30 min, 60 °C

参考文献：

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

Bose, Shubhankar Kumar; et al, ACS Catalysis, 2016, 6(12), 8332-8335

合成路线：1 步

542-18-7

_72%

反应条件：

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; rt; 18 h, rt

参考文献：

Copper(I)-Catalyzed Boryl Substitution of Unactivated Alkyl Halides

Ito, Hajime; et al, Organic Letters, 2012, 14(3), 890-893

合成路线：1 步

542-18-7

_65%

反应条件：

1.1 Reagents: Lithium tert-butoxide Catalysts: Copper, compd. with palladium (2.8:0.2) (graphene supported) Solvents: Dimethylformamide ; 2 h, 50 °C

参考文献：

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

Jiao, Zhi-Feng; et al, Journal of Catalysis, 2021, 395, 258-265

合成路线：1 步

931-50-0

_82%

反应条件：

1.1 Solvents: Tetrahydrofuran ; 1 h, 25 °C
1.2 Reagents: Hydrochloric acid Solvents: Water

参考文献：

Hydride as a Leaving Group in the Reaction of Pinacolborane with Halides under Ambient Grignard and Barbier Conditions. One-Pot Synthesis of Alkyl, Aryl, Heteroaryl, Vinyl, and Allyl Pinacolboronic Esters

Clary, Jacob W.; et al, Journal of Organic Chemistry, 2011, 76(23), 9602-9610

合成路线：1 步

110-82-7

_81%

反应条件：

1.1 Reagents: Cupric chloride , 2,2′-Bi-1,3,2-benzodioxaborole Solvents: Acetonitrile ; 18 h, rt
1.2 Reagents: Triethylamine ; 4 h, rt

参考文献：

Photoinduced C(sp3)-H borylation of alkanes mediated by copper(II) chloride

Fang, Wen; et al, Chemical Communications (Cambridge, 2023, 59(46), 7108-7111

合成路线：1 步

110-82-7

_68%

反应条件：

1.1 Reagents: 2,2′-Bi-1,3,2-benzodioxaborole Catalysts: Cupric chloride Solvents: Acetonitrile ; 10 h, rt
1.2 16 h, 40 °C
1.3 Reagents: Triethylamine Solvents: Dichloromethane ; 1 h, rt

参考文献：

Copper-Mediated Dehydrogenative C(sp3)-H Borylation of Alkanes

Sang, Ruocheng ; et al, Journal of the American Chemical Society, 2023, 145(28), 15207-15217

合成路线：1 步

1632411-83-6

_78%

反应条件：

1.1 Catalysts: Ferrous bromide , Dibromo[1,1′-oxybis[ethane]]magnesium Solvents: Tetrahydrofuran ; 1 h, rt

参考文献：

Iron-Catalyzed Borylation of Alkyl, Allyl, and Aryl Halides: Isolation of an Iron(I) Boryl Complex

Bedford, Robin B.; et al, Organometallics, 2014, 33(21), 5940-5943

合成路线：1 步

_78%

反应条件：

1.1 Catalysts: Bis(1,5-cyclooctadiene)nickel , Tri-tert-butylphosphine Solvents: Methanol , Toluene ; 10 h, 75 °C

参考文献：

Base-free nickel-catalyzed hydroboration of simple alkenes with bis(pinacolato)diboron in an alcoholic solvent

Li, Jiang-Fei; et al, Green Chemistry, 2017, 19(19), 4498-4502

合成路线：1 步

_43%

反应条件：

1.1 Reagents: Potassium tert-butoxide Catalysts: 2659230-20-1 Solvents: Acetonitrile , Water ; 6 h, rt

参考文献：

Copper-Photocatalyzed Hydroboration of Alkynes and Alkenes

Zhong, Mingbing; et al, Angewandte Chemie, 2021, 60(26), 14498-14503

合成路线：1 步

1632411-83-6

_78%

反应条件：

1.1 Catalysts: Ferrous bromide , Dibromo[1,1′-oxybis[ethane]]magnesium Solvents: Tetrahydrofuran ; 1 h, rt

参考文献：

Iron-Catalyzed Borylation of Alkyl, Allyl, and Aryl Halides: Isolation of an Iron(I) Boryl Complex

Bedford, Robin B.; et al, Organometallics, 2014, 33(21), 5940-5943

合成路线：1 步

_76%

反应条件：

1.1 Reagents: 2,2′-Bi-1,3,2-benzodioxaborole Solvents: Dimethylacetamide ; 14 h, rt
1.2 Reagents: Triethylamine ; 1 h, rt

参考文献：

Photoinduced Deaminative Borylation of Alkylamines

Wu, Jingjing; et al, Journal of the American Chemical Society, 2018, 140(34), 10700-10704

合成路线：1 步

_73%

反应条件：

1.1 Reagents: 2,2′-Bi-1,3,2-benzodioxaborole Catalysts: 4,4′-Bis(1,1-dimethylethyl)-2,2′-bipyridine Solvents: Dimethylacetamide ; 6 h, 100 °C; 100 °C → rt
1.2 Reagents: Triethylamine ; 1 h, rt

参考文献：

Selective C-N Borylation of Alkyl Amines Promoted by Lewis Base

Hu, Jiefeng; et al, Angewandte Chemie, 2018, 57(46), 15227-15231

合成路线：1 步

_69%

反应条件：

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

参考文献：

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

Sandfort, Frederik; et al, Chemistry - A European Journal, 2018, 24(65), 17210-17214

合成路线：1 步

2925076-96-4

_69%

反应条件：

1.1 Reagents: 2,2′-Bi-1,3,2-benzodioxaborole Catalysts: Tris[2-[4-(1,1-dimethylethyl)-2-pyridinyl-κN]-3,5-difluorophenyl-κC]iridium Solvents: Ethyl acetate , Hexamethylphosphoramide ; 14 h, rt
1.2 Reagents: Triethylamine ; 1 h, rt

参考文献：

Decarboxylative Borylation of Stabilized and Activated Carbon Radicals

Zhang, Qiang; et al, Angewandte Chemie, 2020, 59(49), 21875-21879

合成路线：1 步

_67%

反应条件：

1.1 Reagents: Pyridine-borane , Iodine Solvents: Dichloromethane ; 0 °C; 0 °C → rt
1.2 2 h, rt; rt → 0 °C
1.3 Reagents: Sodium hydroxide Solvents: Water ; 0 °C → rt
1.4 Solvents: Dichloromethane ; 15 h, rt

参考文献：

Formation of Pinacol Boronate Esters via Pyridine Iodoborane Hydroboration

Karatjas, Andrew G.; et al, Journal of Organic Chemistry, 2008, 73(23), 9508-9510

合成路线：1 步

_52%

反应条件：

1.1 Reagents: Diisopropylethylamine , Boron tribromide Solvents: Dichloromethane ; 0 °C; 12 - 48 h, rt
1.2 Reagents: Triethylamine Solvents: Dichloromethane ; 1 h, rt

参考文献：

Site-Fixed Hydroboration of Terminal and Internal Alkenes using BX3/iPr2NEt

Li, Sida; et al, Angewandte Chemie, 2021, 60(50), 26238-26245

合成路线：1 步

_52%

反应条件：

1.1 Reagents: N,N-Diethyl-2-propanamine , Boron tribromide Solvents: Dichloromethane ; 0 °C; 12 h, rt
1.2 Reagents: Triethylamine Solvents: Dichloromethane ; 1 h, rt

参考文献：

Site-fixed hydroboration of alkenes under metal-free conditions: scope and mechanistic studies

Li, Sida; et al, ChemRxiv, 2021, 1, 1-15

合成路线：1 步

1619237-57-8

_60%