883-39-6 (1-苯基-1H-苯并[D][1,2,3]三唑,1-Phenyl-1H-benzod1,2,3triazole)

_98%

反应条件：

1.1 Reagents: Potassium carbonate Catalysts: Copper oxide (CuO) Solvents: Dimethylformamide ; 3 h, reflux

参考文献：

Room temperature N-arylation of 1,2,4-triazoles under ligand-free condition

Suramwar, Nikhil V.; et al, Organic Chemistry International, 2012, 515092,

合成路线：1 步

591-50-4

_98%

反应条件：

1.1 Reagents: Potassium carbonate Catalysts: Hexadecyltrimethylammonium bromide , [Bis(diphenylphosphino)ethane]dichloropalladium , Cyclopropanecarboxylic acid, 2-phenyl-, copper(2+) salt (2:1) Solvents: Dimethylformamide

参考文献：

Pd- and Cu-catalyzed selective arylation of benzotriazole

Beletskaya, Irina P.; et al, Tetrahedron Letters, 1998, 39(31), 5617-5620

合成路线：1 步

591-50-4

_97%

反应条件：

1.1 Reagents: Potassium carbonate Catalysts: Copper oxide (CuO) Solvents: Dimethylformamide ; 5 h, reflux

参考文献：

Tamarix gallica leaf extract mediated novel route for green synthesis of CuO nanoparticles and their application for N-arylation of nitrogen-containing heterocycles under ligand-free conditions

Nasrollahzadeh, Mahmoud; et al, RSC Advances, 2015, 5(51), 40628-40635

合成路线：1 步

_96%

反应条件：

1.1 Reagents: Tetrabutylammonium fluoride Solvents: Dichloromethane

参考文献：

A convenient and efficient synthesis of benzotriazoles and benzisoxazolines using a new hypervalent iodine-benzyne precursor

Kitamura, Tsugio; et al, Heterocyclic Communications, 1998, 4(3), 205-208

合成路线：1 步

_96%

反应条件：

1.1 Reagents: Sodium hydroxide Catalysts: Palladium diacetate , Benzenesulfonic acid, 3,3′,3′′-phosphinidynetris-, sodium salt (1:3) , Cyclopropanecarboxylic acid, 2-phenyl-, copper(2+) salt (2:1) Solvents: Water

参考文献：

Pd- and Cu-catalyzed selective arylation of benzotriazole by diaryliodonium salts in water

Beletskaya, Irina P.; et al, Tetrahedron Letters, 1998, 39(31), 5621-5622

合成路线：1 步

_80%

反应条件：

1.1 Reagents: Potassium carbonate Catalysts: Copper(II) acetylacetonate Solvents: Toluene

参考文献：

Copper-catalyzed N-arylation of amines with hypervalent iodonium salts

Kang, Suk-Ku; et al, Synlett, 2000, (7), 1022-1024

合成路线：1 步

108-86-1

_95%

反应条件：

1.1 Reagents: Potassium carbonate Catalysts: Cuprous iodide , L-Proline, ion(1-), 3,3′-[[5,11,17,23-tetrakis(1,1-dimethylethyl)-26,28-bis(phen… Solvents: Water ; 30 min, rt; 10 min, 140 °C

参考文献：

Highly Efficient C-N Bond Forming Reactions in Water Catalyzed by Copper(I) Iodide with Calix[4]arene Supported Amino Acid Ionic Liquid

Huang, Li; et al, Chinese Journal of Chemistry, 2012, 30(10), 2394-2400

合成路线：1 步

108-86-1

_93%

反应条件：

1.1 Reagents: Potassium carbonate Catalysts: Cuprous iodide , 1H-Imidazolium, 3-[(4-ethenylphenyl)methyl]-1,2-dimethyl-, chloride (1:1), polym… (reaction products with sodium hydroxide and L-proline) , L-Proline, ion(1-), 1,2,3-trimethyl-1H-imidazolium (1:1) (polystyrene-supported) Solvents: Dimethyl sulfoxide ; 30 min, rt; 60 h, 120 °C; 120 °C → rt

参考文献：

A Concept of Supported Amino Acid Ionic Liquids and Their Application in Metal Scavenging and Heterogeneous Catalysis

Chen, Wen; et al, Journal of the American Chemical Society, 2007, 129(45), 13879-13886

合成路线：1 步

108-86-1

_75%

反应条件：

1.1 Reagents: Potassium tert-butoxide Catalysts: Copper iron oxide (CuFe2O4) Solvents: Dimethylformamide ; 24 h, reflux

参考文献：

Copper ferrite nanoparticle-mediated N-arylation of heterocycles: a ligand-free reaction

Panda, Niranjan; et al, Tetrahedron Letters, 2011, 52(16), 1924-1927

合成路线：1 步

534-85-0

_95%

反应条件：

1.1 Reagents: Nitrogen trioxide Solvents: Acetonitrile ; 10 min, 5 bar, 20 °C

参考文献：

On Demand Flow Platform for the Generation of Anhydrous Dinitrogen Trioxide and Its Further Use in N-Nitrosative Reactions

Chen, Yuesu ; et al, Angewandte Chemie, 2022, 61(41),

合成路线：1 步

1256156-55-4

_92%

反应条件：

1.1 Reagents: Potassium carbonate Catalysts: Cuprous iodide Solvents: Water , Polyethylene glycol ; 2.5 h, 110 °C

参考文献：

A ligand-free copper (1) catalysed intramolecular N-arylation of diazoaminobenzenes in PEG-water: an expeditious protocol towards regiospecific 1-aryl benzotriazoles

Mukhopadhyay, Chhanda; et al, Organic & Biomolecular Chemistry, 2010, 8(20), 4720-4729

合成路线：1 步

1256156-55-4

_73%

反应条件：

1.1 Reagents: Dabco Catalysts: Triphenylphosphine , Dichlorobis(triphenylphosphine)palladium Solvents: Toluene ; 24 h, 80 °C

参考文献：

Selective Synthesis of 3-Arylbenzo-1,2,3-triazin-4(3H)-ones and 1-Aryl-(1H)-benzo-1,2,3-triazoles from 1,3-Diaryltriazenes through Pd(0) Catalyzed Annulation Reactions

Chandrasekhar, Attoor; et al, Journal of Organic Chemistry, 2017, 82(21), 11487-11493

合成路线：1 步

_92%

反应条件：

1.1 Reagents: Cesium fluoride Solvents: Acetonitrile ; 24 h, rt

参考文献：

Facile N-Arylation of Amines and Sulfonamides and O-Arylation of Phenols and Arenecarboxylic Acids

Liu, Zhijian; et al, Journal of Organic Chemistry, 2006, 71(8), 3198-3209

合成路线：1 步

_86%

反应条件：

1.1 Reagents: Potassium fluoride , Sodium azide Solvents: Tetrahydrofuran ; 12 h, 25 °C

参考文献：

Selective Synthesis of N-H and N-Aryl Benzotriazoles by the [3 + 2] Annulation of Sodium Azide with Arynes

Guin, Avishek; et al, Journal of Organic Chemistry, 2019, 84(19), 12692-12699

合成路线：1 步

1295605-37-6

_91%

反应条件：

1.1 Reagents: Potassium acetate Catalysts: Palladium diacetate , 1,3-Bis(diphenylphosphino)propane Solvents: Dimethylformamide ; 12 h, 110 °C

参考文献：

1,7-palladium migration via C-H activation, followed by intramolecular amination: regioselective synthesis of benzotriazoles

Zhou, Jun; et al, Journal of the American Chemical Society, 2011, 133(18), 6868-6870

合成路线：1 步

1295605-37-6

_18%

反应条件：

1.1 Reagents: Potassium acetate , Iodobenzene diacetate Catalysts: Palladium (sulfur-modified gold-supported) Solvents: Dimethylformamide ; 96 h, 120 °C

参考文献：

Palladium-Nanoparticle-Catalyzed 1,7-Palladium Migration Involving C-H Activation, Followed by Intramolecular Amination: Regioselective Synthesis of N1-Arylbenzotriazoles and an Evaluation of Their Inhibitory Activity toward Indoleamine 2,3-Dioxygenase

Takagi, Koji; et al, Journal of Organic Chemistry, 2014, 79(13), 6366-6371

合成路线：1 步

1983774-30-6

_91%

反应条件：

1.1 Reagents: Diboronic acid Solvents: Acetonitrile ; 2 h, 50 °C

参考文献：

The Disappearing Director: The Case of Directed N-Arylation via a Removable Hydroxyl Group

Andrzejewska, Magdalena R.; et al, Advanced Synthesis & Catalysis, 2018, 360(13), 2503-2510

合成路线：1 步

1242566-87-5

_90%

反应条件：

1.1 Reagents: Sodium tert-butoxide Catalysts: 1,10-Phenanthroline , Cuprous iodide Solvents: Dimethyl sulfoxide ; 10 h, 135 - 140 °C

参考文献：

A Novel and regiospecific synthesis of 1-aryl-1H-benzotriazoles via copper(I)-catalyzed intramolecular cyclization reaction

Liu, Qi-Lun; et al, Helvetica Chimica Acta, 2010, 93(7), 1350-1354

合成路线：1 步

1242566-87-5

_86%

反应条件：

1.1 Reagents: Potassium carbonate Catalysts: Palladium diacetate , [1,1′-Bis(diphenylphosphino)ferrocene]dichloropalladium Solvents: Toluene ; 12 h, 110 °C

参考文献：

Synthesis of functionized N-arylbenzotriazoles via palladium catalyzed intramolecular amination

Wang, Dachao; et al, Tetrahedron Letters, 2022, 88,

合成路线：1 步

62-53-3

_89%

反应条件：

1.1 Reagents: tert-Butyl nitrite Solvents: Acetonitrile ; rt
1.2 Reagents: Azidotrimethylsilane ; rt; 1 h, rt
1.3 Reagents: Cesium fluoride ; overnight, rt

参考文献：

Benzyne Click Chemistry with in Situ Generated Aromatic Azides

Zhang, Fengzhi; et al, Organic Letters, 2009, 11(7), 1587-1590

合成路线：1 步

98-80-6

_89%

反应条件：

1.1 Catalysts: 2252271-43-3 Solvents: Methanol ; 22 h, rt
1.2 Reagents: Water ; rt

参考文献：

N,O-Bidentate ligand-tunable copper(II) complexes as a catalyst for Chan-Lam coupling reactions of arylboronic acids with 1H-imidazole derivatives

Jia, Xuefeng; et al, Organic & Biomolecular Chemistry, 2018, 16(46), 8984-8988

合成路线：1 步

98-80-6

_80%

反应条件：

1.1 Reagents: Sodium tert-butoxide Catalysts: Copper, [N,N′-bis[2-(hydroxy-κO)phenyl]-2,6-pyridinedicarboxamidato(2-)-κN1,κO2,… ; 4 h, 120 °C

参考文献：

Cu(II) complex of pyridine-based polydentate as a novel, efficient, and highly reusable catalyst in C-N bond-forming reaction

Sharghi, Hashem; et al, Molecular Diversity, 2017, 21(4), 855-864

合成路线：1 步

98-80-6

_54%

反应条件：

1.1 Reagents: Sodium carbonate Catalysts: 2992619-64-2 Solvents: Methanol ; 24 h, 70 °C

参考文献：

Cu-NHC Complex for Chan-Evans-Lam Cross-Coupling Reactions of N-Heterocyclic Compounds and Arylboronic Acids

Adhikari, Bhupendra; et al, European Journal of Organic Chemistry, 2023, 26(40),

合成路线：1 步

1608-42-0

_88%

反应条件：

1.1 Solvents: tert-Butanol

参考文献：

Benzyne as a dipolarophile

Huisgen, Rolf; et al, Naturwissenschaften, 1962, 48,

合成路线：1 步

_87%

反应条件：

1.1 Reagents: Cesium fluoride Solvents: Acetonitrile ; 18 h, rt

参考文献：

Benzyne click chemistry: synthesis of benzotriazoles from benzynes and azides

Shi, Feng; et al, Organic Letters, 2008, 10(12), 2409-2412

合成路线：1 步

反应条件：

1.1 Reagents: Tetrabutylammonium fluoride Solvents: Acetonitrile ; overnight, rt

参考文献：

Photochemical C-H Activation: Generation of Indole and Carbazole Libraries, and First Total Synthesis of Clausenawalline D

Alimi, Isak; et al, European Journal of Organic Chemistry, 2017, 2017(22), 3197-3210

合成路线：1 步

_84%

反应条件：

1.1 Reagents: Cesium carbonate Catalysts: Copper Solvents: Acetonitrile ; 24 h, 80 °C

参考文献：

Cu-catalyzed arylation of 1-acyl-1H-1,2,3-Benzotriazoles via C-N activation

Zhang, Wenying; et al, Journal of Organometallic Chemistry, 2019, 895, 64-67

合成路线：1 步

_84%

反应条件：

1.1 Catalysts: Palladium Solvents: Acetonitrile ; 30 min, rt
1.2 12 h, reflux

参考文献：

Pd/Al2O3-catalysed regioselective N-1-modification of benzotriazoles using iodonium salts

Davydov, Dmitry V.; et al, Tetrahedron Letters, 2017, 58(47), 4465-4467

合成路线：1 步

1651824-88-2

_82%

反应条件：

1.1 Reagents: Cesium carbonate Catalysts: 18-Crown-6 Solvents: Acetonitrile ; 12 h, 30 °C
1.2 Reagents: Ammonium chloride Solvents: Water

参考文献：

Development and Application of O-(Trimethylsilyl)aryl Fluorosulfates for the Synthesis of Arynes

Chen, Qiao; et al, Journal of Organic Chemistry, 2015, 80(13), 6890-6896

合成路线：1 步

136-35-6

_80%

反应条件：

1.1 Reagents: Oxygen Catalysts: Palladium diacetate Solvents: Dimethylformamide ; 110 °C; 110 °C → rt

参考文献：

Pd-Catalyzed C-H Activation/C-N Bond Formation: A New Route to 1-Aryl-1H-benzotriazoles

Kumar, Rapolu Kiran; et al, Organic Letters, 2011, 13(8), 2102-2105

合成路线：1 步

95-51-2

62-53-3

_78%