1373397-31-9

Upstream product

• 1373397-22-8 4-fluoro-2-(trimethylsilyl)phenyl 1-imidazolsulfonate 
• 622-79-7 benzyl azide 
• 1313182-67-0 4-fluoro-2,6-bis(trimethylsilyl)phenol 
• 1313182-65-8 2-bromo-4-fluoro-6-(trimethylsilyl)phenol 
• 1313182-66-9 trimethylsilyl 2-bromo-4-fluoro-6-(trimethylsilyl)phenyl ether 
• 1313182-68-1 4-fluoro-2,6-bis(trimethylsilyl)phenyl trifluoromethanesulfonate 
• 1308789-55-0 m-fluorophthaloyl peroxide 
• 62366-71-6 m-fluorophthaloyl chloride 
• 129353-89-5 4-fluoro-2-(trimethylsilyl)phenol 
• 371-41-5 4-Fluorophenol 
• 100-52-7 benzaldehyde 
• 371-40-4 4-fluoroaniline 
• 184832-35-7 N¹-benzyl-4-fluorobenzene-1,2-diamine 
• 370-77-4 N-benzyl-p-fluoroaniline 

Relevant academic research and scientific papers

Scalable Synthesis of Benzotriazoles via [3+2] Cycloaddition of Azides and Arynes in Flow

A method for the metal-free synthesis of benzotriazoles in flow is reported. Using azides and in situ generated arynes, benzotriazoles are formed in a [3+2] cycloaddition within minutes. Employing different substitution patterns of the azide and aryne coupling partners, a modular access to benzotriazoles is provided. Thermal strain of hazardous azides and accumulation of reactive intermediates is minimized by short reaction times in flow, improving the safety profile of the process. The scalability of the reaction is demonstrated.

Regioselective Nitration of N-Alkyl Anilines using tert-Butyl Nitrite under Mild Condition

Regioselective ring nitration of N-alkyl anilines is reported using tert-butyl nitrite. The reactions proceed efficiently with a wide range of substrates providing synthetically useful N-nitroso N-alkyl nitroanilines in excellent yields which can be easily converted into N-alkyl phenylenediamines and N-alkyl nitroanilines using Zn-AcOH and HCl/MeOH, respectively.

Enhancing the synthetic utility of 3-haloaryne intermediates by their efficient Generation from readily synthesizable ortho-iodoaryl triflate-type precursors

Generation of 3-haloarynes from o-iodoaryl triflate-type precursors is reported. The method enables the generation of 3-fluorobenzyne with significantly high electrophilicity at -78 °C, allowing the formation of a three-component-coupled product between 3

Cycloadditions of azides with arynes via photolysis of phthaloyl peroxide derivatives

Photolysis of phthaloyl peroxides yields arynes, which undergo [3 + 2] cycloadditions with azides. This reaction tolerates a variety of organic azides and phthaloyl peroxides and affords the corresponding benzotriazoles in moderate to good yields at room

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

Regiocomplementary cycloaddition reactions of boryl- and silylbenzynes with 1,3-dipoles: Selective synthesis of benzo-fused azole derivatives

Benzo-fused nitrogen-containing heterocycles are abundant in biologically active compounds. One of the most important methods for preparing such heterocycles is the (3 + 2) cycloaddition reaction of benzynes with 1,3-dipolar compounds. However, the reacti

Design and application of new imidazolylsulfonate-based benzyne precursor: An efficient triflate alternative

Several o-(trimethylsilyl)aryl imidazolylsulfonates were synthesized in a simple process and successfully applied in cycloadditions involving benzyne intermediates. The precursor offers an efficient alternative for generating benzynes compared to widely used ortho TMS triflates under similar reaction conditions. With the utilization of this new precursor, the formation of potentially genotoxic trifluoromethanesulfonate side product is eliminated. The applicability of the new benzyne precursor was demonstrated in different types of cycloaddition reactions to prepare heterocyclic molecules.