179029-65-3

Upstream product

• 6292-59-7 4-tert-butylbenzenesulphonamide 
• 15084-51-2 4-tert-butylbenzenesulfonyl chloride 
• 65604-75-3 4-(tert-butyl)benzenesulfonyl hydrazide 

Downstream Products

• 1006728-09-1 2-(p-(tert-butyl)benzenesulfonylimino)-1-methylindoline 
• 1006728-15-9 C₂₅H₂₆N₄O₄S₂ 
• 477482-92-1 N-(2,4,6-trimethylphenyl)-4-tert-butylbenzenesulfonamide 

Relevant academic research and scientific papers

Convenient synthesis of spiroindolenines from tryptamine-derived isocyanides and organic azides by cobalt catalysis in pure water

A Co-catalyzed coupling of 3-(2-isocyanoethyl)indoles with organic azides in pure water for accessing spiroindolenine derivatives was developed. This strategy features mild reaction conditions, high atom-economy, excellent yields, wide substrate scopes, and broad functional group tolerance. The products were obtained simply by sequential operation involving extraction, concentration, precipitation, and filtration, without tedious column chromatography. More importantly, the aqueous catalytic system could be recycled at least ten times without reducing the catalytic activity. The strategy provides a green and efficient method for the construction of spiroindolenine derivatives.

Diversity Oriented Clicking (DOC): Divergent Synthesis of SuFExable Pharmacophores from 2-Substituted-Alkynyl-1-Sulfonyl Fluoride (SASF) Hubs

Diversity Oriented Clicking (DOC) is a unified click-approach for the modular synthesis of lead-like structures through application of the wide family of click transformations. DOC evolved from the concept of achieving “diversity with ease”, by combining classic C?C π-bond click chemistry with recent developments in connective SuFEx-technologies. We showcase 2-Substituted-Alkynyl-1-Sulfonyl Fluorides (SASFs) as a new class of connective hub in concert with a diverse selection of click-cycloaddition processes. Through the selective DOC of SASFs with a range of dipoles and cyclic dienes, we report a diverse click-library of 173 unique functional molecules in minimal synthetic steps. The SuFExable library comprises 10 discrete heterocyclic core structures derived from 1,3- and 1,5-dipoles; while reaction with cyclic dienes yields several three-dimensional bicyclic Diels–Alder adducts. Growing the library to 278 discrete compounds through late-stage modification was made possible through SuFEx click derivatization of the pendant sulfonyl fluoride group in 96 well-plates—demonstrating the versatility of the DOC approach for the rapid synthesis of diverse functional structures. Screening for function against MRSA (USA300) revealed several lead hits with improved activity over methicillin.

Regioselective C-H Amidation of (Alkyl)arenes by Iron(II) Catalysis

A nondirected amidation reaction of aromatic C-H bond was developed under iron(II) catalysis, using sulfonyl azides as the nitrogen source. The reaction displayed a broad substrate scope and good regioselectivities in the aspects of aromatic ring vs alkyl

Photoinduced Cascade Reaction of Tertiary Amines with Sulfonyl Azides: Synthesis of Amidine Derivatives

A metal-free cascade reaction of tertiary amines with sulfonyl azides promoted by acridinium salts under blue light irradiation was developed and provided amidine derivatives in moderate to good yields. Enamine was generated from tertiary amine via single-electron transfer promoted by acridinium salts, and the following [3+2] cyclization with sulfonyl azide and CH2N2 release afforded the desired products. (Figure presented.).

Nitroacenaphthene as a New Photocatalyst for the Synthesis of Sulfonyl Amidines

A small molecule, namely nitroacenaphthene, is reported for the first time as a recyclable visible-light photocatalyst for the construction of the C=N bond from sulfonyl azides and amines. This scalable, site-selective protocol provides a convenient way to access various sulfonyl amidines under mild conditions. Two reaction pathways are proposed, according to different transformation patterns.

Tert -Butyl nitrite mediated nitrogen transfer reactions: Synthesis of benzotriazoles and azides at room temperature

A conversion of o-phenylenediamines into benzotriazoles was achieved at room temperature using tert-butyl nitrite. The optimized conditions are also well suited for the transformation of sulfonyl and acyl hydrazines into corresponding azides. This protocol does not require any catalyst or acidic medium. The desired products were obtained in excellent yields in a short span of time.

Iridium(III)-Catalyzed Regiocontrolled Direct Amidation of Isoquinolones and Pyridones

Iridium(III)-catalyzed highly regiocontrolled C3/C8 amidation of isoquinolones and C6 amidation of 2-pyridones has been successfully accomplished with various azides. The optimized method is operationally simple with a broad substrate scope. The protocol has been found to be scalable. (Figure presented.).

Iridium-Catalysed Cascade Synthesis of Oxindoles Using Diazo Compounds: A Quick Entry to C-7-Functionalized Oxindoles

A cascade iridium-catalysed oxindole synthesis was achieved using pyridyl-protected anilines and bis(2,2,2-trifluoroethyl) 2-diazomalonate. The developed protocol is simple and scalable, and has a broad scope and excellent regioselectivity. The pyridyl directing group can easily be removed. The method was further extended to give C-7-functionalized oxindole derivatives in a straightforward manner. The role of bis(2,2,2-trifluoroethyl) 2-diazomalonate for oxindole preparation has been explored.

Iridium(III)-Catalyzed Direct C-H Sulfonamidation of 2-Aryl-1,2,3-triazole N-Oxides with Sulfonyl Azides

We have developed a method for the direct sulfonamidation of 2-aryl-1,2,3-triazole N-oxides using sulfonyl azides as the amino source to release molecular nitrogen as the sole by-product. This protocol exhibits excellent functional group tolerance and proceeds efficiently under external oxidant-free conditions. Various 2-(2-sulfonamidoaryl)-1,2,3-triazoles were prepared in up to 97% yields for 25 examples with excellent regioselectivity.

Transition-metal-free direct amination of simple arenes with sulfonyl azides

A metal-free green protocol has been developed for amination of simple arenes using arylsulfonyl azides via a nitrene transfer process under solvent free conditions at 130 °C releasing N2 gas as the sole by-product.