405198-82-5

Upstream product

• 615-37-2 ortho-methylphenyl iodide 
• 88-67-5 2-Iodobenzoic acid 
• 183789-20-0 2-iodobenzyl methanesulfonate 
• 40400-13-3 2-Iodobenzyl bromide 
• 5159-41-1 2-iodobenzyl alcohol 

Downstream Products

• 874633-59-7 2-[3,5-bis(2-aminomethyl-phenylethynyl)phenylethynyl]benzylamine 
• 874633-58-6 (2-{3,5-bis[2-(tert-butoxycarbonylamino-methyl)phenylethynyl]phenylethynyl}benzyl)carbamic acid tert-butyl ester 
• 405198-83-6 2-iodobenzyl-carbamoyl acid tert-butyl ester 
• 152417-92-0 2-iodobenzyl isothiocyanate 
• 1235527-62-4 1-(2-iodobenzyl)-4-phenyl-1H-1,2,3-triazole 
• 1426579-44-3 1-(2-iodobenzyl)-5-methyl-7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-benzo[d]triazole 
• 1235527-70-4 1-(2-iodobenzyl)-4-(p-tolyl)-1H-1,2,3-triazole 
• 1030862-10-2 1-(2-iodobenzyl)-1H-benzo[d][1,2,3]triazole 
• 405198-84-7 N-[2-[2-(trimethysilyl)ethynyl]benzyl]-(4-methylphenyl)sulfonamide 
• 405198-87-0 N-[2-(1-hexynyl)benzyl]-(4-methylbenzyl)sulfonamide 
• 405198-90-5 N-[2-(3,3-dimethyl-1-butynyl)benzyl]-(4-methylphenyl)sulfonamide 
• 405198-89-2 N-[2-(3-hydroxypropynyl)benzyl]-(4-methylphenyl)sulfonamide 
• 405198-85-8 (2-trimethylsilylethynyl-benzyl)carbamoyl acid tert-butyl ester 

Relevant academic research and scientific papers

Palladium-copper catalysed heteroannulation of acetylenic compounds: An expeditious synthesis of isoindoline fused with triazoles

A convenient and general method for the synthesis of isoindoline fused with triazoles from ortho-iodobenzyl azide and acetylenes through palladium-copper catalysis is described.

Synthesis and characterization of fluorescent-active triazole-gold complexes

Fluorescence active fused-triazole was developed as a ligand in gold(I) cation coordination. The coordination ability was evaluated using NMR and fluorescence emission. Our previously reported N-2-aryl-triazoles, though gave good emission, could not form stable complexes with gold cations. A new N-fused-triazole (NFT) derivative was prepared and the ligand indicated good fluorescence emission, and formed strong coordination with gold cations. Both ligand and complex were characterized by X-ray crystallography. Fluorescence properties of various gold complexes (with different primary ligands) were evaluated, which suggested the feasibility of using fluorescence emission as potential tools for future mechanistic investigation.

Synthesis of 1,2,3,triazole modified analogues of hydrochlorothiazide via click chemistry approach and in-vitro α-glucosidase enzyme inhibition studies

The current study was aimed to discover potent inhibitors of α-glucosidase enzyme. A 25 membered library of new 1,2,3-triazole derivatives of hydrochlorothiazide (1) (HCTZ, a diuretic drug also being used for the treatment of high blood pressure) was synt

Copper-Catalyzed Azide–Ynamide Cyclization to Generate α-Imino Copper Carbenes: Divergent and Enantioselective Access to Polycyclic N-Heterocycles

Here an efficient copper-catalyzed cascade cyclization of azide-ynamides via α-imino copper carbene intermediates is reported, representing the first generation of α-imino copper carbenes from alkynes. This protocol enables the practical and divergent synthesis of an array of polycyclic N-heterocycles in generally good to excellent yields with broad substrate scope and excellent diastereoselectivities. Moreover, an asymmetric azide–ynamide cyclization has been achieved with high enantioselectivities (up to 98:2 e.r.) by employing BOX-Cu complexes as chiral catalysts. Thus, this protocol constitutes the first example of an asymmetric azide–alkyne cyclization. The proposed mechanistic rationale for this cascade cyclization is further supported by theoretical calculations.

Waste-minimised copper-catalysed azide-alkyne cycloaddition in Polarclean as a reusable and safe reaction medium

Herein we report the first example of a generally useful organic reaction, namely the copper-catalysed azide-alkyne cycloaddition, performed in a Polarclean/water mixture as a reaction medium. The process is very efficient, affording in 24 out of the 26 tested cases the desired triazole in quantitative yields. Product isolation is also very convenient, since the triazoles either precipitate or form a separate liquid phase, without the need to perform chromatographic separations. Moreover, since the metal catalyst is retained in the Polarclean/water phase, the catalyst/reaction medium can be easily reused for consecutive reaction runs, without an apparent loss in efficiency. This methodology is associated with very limited waste production, as evidenced by calculated E-factors in the range 2.6-3.7.

Synthesis of diaziridines and diazirines via resin-bound sulfonyl oximes

Diazirines are one of the most prominent functionalities in labeling experiments in vivo and in vitro because they allow photochemical generation of carbenes. The strategy presented herein describes the formation of diaziridines, being essential precursors in diazirine syntheses, using solid-supported procedures with immobilized sulfonyl oximes. The solid-supported building blocks have been shown to be valuable intermediates for CuAAC and amidation reactions, offering the possibility to build complex compounds with diverse functionalities.

Benzylic C-H Azidation Using the Zhdankin Reagent and a Copper Photoredox Catalyst

An azidation method for C-N bond formation at benzylic C-H positions is described using copper-catalyzed visible light photochemistry and the Zhdankin azidoiodinane reagent. The method is applicable to a wide range of substrates bearing different functional groups and having a primary, secondary, or tertiary benzylic position, and is thought to proceed through a radical chain reaction.

Copper promoted synthesis of substituted quinolines from benzylic azides and alkynes

A novel copper promoted synthesis of substituted quinolines from various benzylic azides and internal alkynes has been demonstrated. The reaction features a broad substrate scope, high product yields and excellent regioselectivity. In contrast to the known two-step process of acid promoted [4 + 2] cycloaddition reaction and oxidation, the present methodology allows the synthesis of quinolines in a single step under neutral reaction conditions and can be applied to the synthesis of biologically active 6-chloro-2,3-dimethyl-4-phenylquinoline (antiparasitic agent) and 3,4-diphenylquinolin-2(1H)-one (p38αMAP kinase inhibitor). A plausible reaction mechanism involves rearrangement of benzylic azide to N-arylimine (Schmidt reaction) followed by intermolecular [4 + 2] cycloaddition with internal alkynes.

Palladium and copper-supported on charcoal: A heterogeneous multi-task catalyst for sequential Sonogashira-Click and Click-Heck reactions

This paper describes the development of one-pot sequential Sonogashira-Click and Click-Heck reactions by using Pd-Cu/C as a heterogeneous multi-task catalyst for the synthesis of heterocyclic structures. Details of the optimization studies and the substrate scope are discussed. These methodologies allow the preparation of functionalized triazoles in simple experimental conditions with inexpensive reagents.

Facile synthesis of [1,2,3]-triazole-fused isoindolines, tetrahydroisoquinolines, benzoazepines and benzoazocines by palladium-copper catalysed heterocyclisation

An elegant method for the synthesis of 1,2,3-triazoles fused with five-, six-, seven- and eight-membered benzoheterocycles, including isoindoline, tetrahydroisoquinoline, benzoazepine and benzoazocine, has been developed via palladium-copper catalysed reactions in one-pot. The broad scope of this reaction was illustrated by effecting bis-heteroannulations, synthesis of uracil derivatives of biological interest, and employment of acetylene gas as an inexpensive substrate. The reactions are experimentally simple and utilise easily accessible substrates of different types. Georg Thieme Verlag Stuttgart · New York.