72435-61-1

Upstream product

• 54187-96-1 1-(chloromethyl)-1H-benzotriazole 
• 108-90-7 chlorobenzene 
• 95-14-7 1,2,3-Benzotriazole 
• 104-83-6 1-Chloro-4-(chloromethyl)benzene 
• 104-88-1 4-chlorobenzaldehyde 
• 88-74-4 2-nitro-aniline 
• 622-95-7 4-chlorobenzyl bromide 
• 88284-48-4 2-(trimethylsilyl)phenyl trifluoromethanesulfonate 
• 15288-53-6 o-(trimethylsilyl)phenol 
• 27032-10-6 4-chlorobenzyl azide 
• 106-43-4 para-chlorotoluene 
• 1334478-56-6 Br^(1-)*C₂₀H₁₆Cl₂N₃⁽¹⁺⁾ 
• 1262319-49-2 C₁₉H₁₃ClN₆ 

Downstream Products

• 25115-73-5 2-(4-chlorophenyl)cyclohexanone 
• 1027408-60-1 1-Benzotriazol-1-yl-1-(4-chloro-phenyl)-2,3,3-trimethyl-butan-2-ol 
• 5172-02-1 1-chloro-4-(2-phenylethynyl)benzene 
• 18654-74-5 (E)-1-chloro-4-(pent-1-en-1-yl)benzene 
• 14670-41-8 (Z)-1-chloro-4-(pent-1-en-1-yl)benzene 
• 627088-30-6 C₃₀H₁₉BrClF₃N₄O₂ 
• 627088-31-7 C₃₀H₁₉BrClF₃N₄O 
• 5043-91-4 (E)-4-chloro-4'-methoxystilbene 
• 1657-50-7 (E)-1-(4-chlorophenyl)-2-phenylethene 
• 142819-62-3 1-(benzotriazol-1-yl)-1-(p-chlorophenyl)-2-phenylethylene 

Relevant academic research and scientific papers

Facile one-pot synthesis of diarylacetylenes from arylaldehydes: Via an addition-double elimination process

A practical one-pot protocol has been developed to synthesize diarylacetylenes from arylaldehydes by treatment with 1-(arylmethyl)benzotriazoles and LiN(SiMe3)2. The reaction proceeded through imine formation, Mannich-type addition and double elimination to deliver products in up to 99% yields with broad substrate scope. In addition, gram-scale synthesis of 1-bromo-4-(phenylethynyl)benzene has been demonstrated.

Atom Transfer Radical Polymerization-Inspired Room Temperature (sp3)C-N Coupling

A simple nonphotochemical procedure is reported for Cu(I)-catalyzed C-N coupling of aliphatic halides with amines and amides. The process is loosely based on the Goldberg reaction but takes place readily at room temperature. It uses Cu(I)Br, a commonly used and inexpensive atom transfer radical polymerization precatalyst, along with the cheap ligand N,N,N′,N″,N″-pentamethyldiethylenetriamine, to activate the R-X bond of the substrate via inner-sphere electron transfer. The procedure brings about productive C-N bond formation between a range of alkyl halide substrates with heterocyclic aromatic amines and amides. The mechanism of the coupling step, which was elucidated through application of computational methods, proceeds via a unique Cu(I) → Cu(II) → Cu(III) → Cu(I) catalytic cycle, involving (a) inner-sphere electron transfer from Cu(I) to the alkyl halide to generate the alkyl radical; (b) successive coordination of the N-nucleophile and the radical to Cu(II); and finally reductive elimination. In the absence of a nucleophile, debrominative homocoupling of the alkyl halide occurs. Control experiments rule out SN-type mechanisms for C-N bond formation.

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

A class of o-(trimethylsilyl)aryl fluorosulfates was synthesized by a concise method and successfully used as aryne precursors for the first time. Different trapping agents such as azides, furans, and acyl acetoacetates could successfully react with the a

Reusable ionic liquid-catalyzed oxidative coupling of azoles and benzylic compounds via sp3 C-N bond formation under metal-free conditions

The heterocyclic ionic liquid-catalyzed direct oxidative amination of benzylic sp3 C-H bonds via intermolecular sp3 C-N bond formation for the synthesis of N-alkylated azoles under metal-free conditions is reported for the first time. The catalyst 1-butylpyridinium iodide can be recycled and reused with similar efficacies for at least eight cycles.

Metal-free, highly efficient organocatalytic amination of benzylic C-H bonds

A new synthetic approach toward direct C-N bond formation through sp 3 C-H activation has been developed under metal-free conditions. Both primary and secondary benzylic C-H substrates could react smoothly with various amines to give only mono-amination products with good to excellent yields. The Royal Society of Chemistry 2013.

TBHP/I2-promoted oxidative coupling of azoles with benzyl compounds via cleavage of nonactivated C(sp3)-H bonds under solvent-free conditions

A novel and efficient TBHP/I2-promoted oxidative coupling of azoles with benzyl compounds via cleavage of nonactivated C(sp3)-H bonds under metal-free, base-free, and solvent-free conditions for the synthesis of N-alkylated azoles has been developed. The procedure, using I2 as the catalyst, is a simple, economical, and environmentally friendly protocol, which could be applied to various available substrates in moderate to good yields. Georg Thieme Verlag Stuttgart. New York.

Reactivity of AllylSmBr/HMPA: Facile Synthesis of 3-Aryl-1,2,4- benzotriazines

3-Aryl-1,2,4-benzotriazines were conveniently prepared in moderate to good yields from 1,l-bis(benzotriazol-1-yl)methylarenes with allylsamarium bromide/hexamethylphosphramide (allylSmBr/HMPA). Preliminary results indicate that HMPA may enhance the reduci

Convenient and stereoselective synthesis of symmetrical (E)-stilbenes via homocoupling of 1,3-dibenzylbenzotriazolium bromides

Using NaH as the base and DMSO as the solvent, a series of symmetric (E)-stilbenes were prepared in good yields via the -homocoupling of 1,3-dibenzylbenzotriazolium bromides at room temperature. Georg Thieme Verlag Stuttgart · New York.

Construction of 3-aryl-1,2,4-benzotriazines via unprecedented rearrangement of bis(benzotriazol-1-yl)methylarenes

3-Aryl-1,2,4-benzotriazines were formed unexpectedly by the treatment of 1,l-bis(benzotriazol-1-yl)methylarenes with allylsamarium bromide. A radical pathway was proposed involving steps, such as fragmentation, ring-opening, and cyclization.

Synthesis of 1H-benzotriazoles via reductive amination on solid supports

An efficient synthesis of N-benzyl-1H-benzotriazoles utilizing a two-step reductive amination reaction on solid supports has been achieved. The method is suitable for combinatorial synthesis. Georg Thieme Verlag Stuttgart.